docs(readme): clarify /loop runs a prompt or custom command, not built-ins

- stopLoop re-arms the poll ticker after removing one loop, so stopping one of
  several no longer strands the rest with no tick scheduled (jatmn).
- a bare self-paced /command is rejected with a pointer to the interval form:
  self-paced drives a free-form goal via the playbook + LOOP: control line, which
  a custom command's expanded template never carries, so it would silently
  degrade to adaptive polling (jatmn).
- /resume only tears loops down on an actual session-id change; /resume latest or
  /resume <currentID> can resolve to the already-active session, whose loops are
  its own, not a "previous" session's (CodeRabbit).
- tests: skipped-behind-modal loop stays scheduled, footer carries the next-wake
  time, the confirmed /clear actually wipes the transcript, plus multi-loop stop
  keeping the ticker alive and self-paced-/command rejection.

.github/workflows/ci.yml

@@ -100,9 +100,10 @@ jobs:
           go-version-file: go.mod
           cache: true
 
-      # govulncheck and deadcode resolve a toolchain from their own modules, which
-      # can drop below the version go.mod requires and then fail to load our
-      # packages. Pin GOTOOLCHAIN to the go.mod toolchain so both run under it.
+      # govulncheck, deadcode, and golangci-lint each resolve a toolchain from
+      # their own modules, which can drop below the version go.mod requires and
+      # then fail to load our packages. Pin GOTOOLCHAIN to the go.mod toolchain
+      # so all three run under it.
       - name: Pin toolchain from go.mod
         run: |
           toolchain="$(awk '/^toolchain /{print $2}' go.mod)"
@@ -120,3 +121,13 @@ jobs:
       - name: deadcode (advisory)
         continue-on-error: true
         run: go run golang.org/x/tools/cmd/[email protected] -test=false ./...
+
+      # Advisory: catches what deadcode's whole-program reachability analysis
+      # doesn't, unused private functions/assignments reachable within a
+      # package but never actually called, plus staticcheck-style correctness
+      # and readability issues. Scoped to a few linters rather than the full
+      # default battery, and non-blocking, while the existing findings across
+      # the repo are cleaned up incrementally (see #527).
+      - name: golangci-lint (advisory)
+        continue-on-error: true
+        run: go run github.com/golangci/golangci-lint/v2/cmd/[email protected] run --enable-only unused,ineffassign,staticcheck ./...

.gitignore

@@ -37,6 +37,7 @@ report.[0-9]_.[0-9]_.[0-9]_.[0-9]_.json
 
 /zero
 /zero.exe
+/zero-skills
 /snake-game.html
 
 # Superpowers skill artifacts (brainstorm mockups, specs, plans) — local only

README.md

@@ -186,6 +186,7 @@ Common slash commands:
 | `/spec`, `/plan` | draft and review a plan before building |
 | `/image` | attach an image for vision-capable models |
 | `/resume`, `/rewind` | continue or roll back local sessions |
+| `/loop` | repeat a prompt or custom `/command` on an interval (`/loop 5m /babysit-prs`) or self-paced |
 | `/compact`, `/context` | manage context usage |
 | `/permissions`, `/tools` | inspect available tools and policy |
 | `/add-dir` | allow an extra write directory for this session |
@@ -283,6 +284,39 @@ zero cron             scheduled agent jobs
 zero update           check for newer releases
 ```
 
+## Extending Zero
+
+### Project and personal instructions
+
+Zero appends project-specific guidance to the system prompt from the first
+`AGENTS.md`, `ZERO.md`, or `.zero/AGENTS.md` file found in each directory from
+the git root down to your current working directory (checked in that order
+per directory). Files are injected general-to-specific, capped at 8 KiB per
+file and 32 KiB total.
+
+A personal `ZERO.md` under `config.UserConfigDir()/zero/ZERO.md`
+(`$XDG_CONFIG_HOME/zero/ZERO.md` or `~/.config/zero/ZERO.md` on Linux/macOS,
+`%AppData%\Roaming\zero\ZERO.md` on Windows) applies across every workspace, ahead of any project guidelines.
+
+### Plugins
+
+Plugins are discovered from `~/.config/zero/plugins/<name>/plugin.json` (user
+scope — `$XDG_CONFIG_HOME` or `~/.config` on every OS, independent of the
+`config.UserConfigDir()` path used above) and `<cwd>/.zero/plugins/<name>/plugin.json`
+(project scope — resolved from the current working directory, not the repo
+root), and managed with `zero plugins`. A manifest can declare:
+
+- `tools` — custom tools (`command`, `args`, `inputSchema`, and a
+  `permission` of `prompt` or `deny`; `allow` is honored only when manifest tool
+  auto-approval is enabled)
+- `hooks` — commands run on `beforeTool`, `afterTool`, `sessionStart`, or
+  `sessionEnd`
+- `prompts` and `skills` — additional prompt/skill files
+
+MCP servers (`zero mcp`) and standalone markdown skills (`zero skills`) use
+the same extension points and can also be wired up outside of a plugin
+manifest.
+
 ## Appearance And Accessibility
 
 | Control | Effect |

action.yml

@@ -180,6 +180,7 @@ runs:
         ZERO_INPUT_ADD_DIR: ${{ inputs.add-dir }}
         ZERO_INPUT_WORKTREE: ${{ inputs.worktree }}
         ZERO_INPUT_OUTPUT_FORMAT: ${{ inputs.output-format }}
+        ACTION_PATH: ${{ github.action_path }}
         RUNNER_TEMP: ${{ runner.temp }}
       run: |
         set -euo pipefail
@@ -247,10 +248,9 @@ runs:
         echo "exit-code=${code}" >> "${GITHUB_OUTPUT}"
         echo "output-file=${output_file}" >> "${GITHUB_OUTPUT}"
 
-        # Best-effort one-line summary: last non-empty line of the captured output.
-        summary="$(grep -v '^[[:space:]]*$' "${output_file}" | tail -n 1 || true)"
-        # Keep the summary single-line and bounded for the step output.
-        summary="$(printf '%s' "${summary}" | cut -c1-280)"
+        # Best-effort one-line summary. Structured output ends with lifecycle
+        # metadata, so parse final/error events instead of tailing stdout.
+        summary="$(node "${ACTION_PATH}/scripts/action-summary.mjs" "${ZERO_INPUT_OUTPUT_FORMAT}" "${output_file}" || true)"
         {
           echo "summary<<ZERO_EOF"
           printf '%s\n' "${summary}"

internal/agent/async_diagnostics.go

@@ -0,0 +1,185 @@
+package agent
+
+import (
+	"context"
+	"path/filepath"
+	"sort"
+	"strings"
+	"sync"
+	"time"
+)
+
+// Post-edit LSP diagnostics used to run synchronously inside edit_file /
+// write_file: every edit blocked its tool result on a fresh-publish wait with
+// a quiet-period debounce (≥300ms floor that reset on each publish, 10s cap) —
+// the largest recurring latency tax in an edit-heavy session. Collection is
+// now asynchronous: a file is enqueued the moment a mutating tool finishes, a
+// single worker checks it while the rest of the tool batch (and any
+// self-correct verification) runs, and the loop drains completed results just
+// before building the NEXT provider request, appending errors as a user-role
+// nudge. The model always issues another request after an edit turn — it has
+// to read its tool results — so it still sees introduced errors at the same
+// decision point as before, without any tool call stalling on the language
+// server.
+//
+// A file re-edited before its check runs is checked once in its final state
+// (the checker re-reads the file); a file re-edited after its check completed
+// is re-enqueued and the newer result wins. When the worker is still busy at
+// drain time, the drain gives up after a short wait and the results are
+// delivered on the following turn instead — they stay accurate because any
+// further edit re-enqueues the file.
+
+// asyncDiagnosticsDrainTimeout bounds how long a turn waits on the in-flight
+// check before deferring delivery to the next turn. Most checks finish well
+// under it (debounce floor + analysis); a cold language server on a large
+// repo does not get to stall the loop the way the old inline 10s cap could.
+// A var so tests can shorten the wait.
+var asyncDiagnosticsDrainTimeout = 3 * time.Second
+
+// asyncDiagnosticsFinalDrainTimeout is the wait used when the run is about to
+// FINALIZE (natural completion or the max-turns summary): there is no later
+// turn to defer to, so the gate waits out the old inline-era budget rather
+// than silently dropping an error the last edit introduced. A var so tests
+// can shorten the wait.
+var asyncDiagnosticsFinalDrainTimeout = 10 * time.Second
+
+// asyncDiagnosticsNudge prefixes the drained diagnostics blocks; phrased like
+// the old inline block so the model reacts the same way.
+const asyncDiagnosticsNudge = "Diagnostics after your recent edits (fix any errors you introduced):\n"
+
+type asyncDiagnostics struct {
+	check         func(context.Context, string) string
+	workspaceRoot string
+
+	mu      sync.Mutex
+	queue   []string
+	queued  map[string]bool
+	results map[string]string
+	// working is non-nil while the worker goroutine runs and is closed when it
+	// exits, so drain can wait for quiescence without polling.
+	working chan struct{}
+}
+
+// newAsyncDiagnostics returns nil when check is nil, and every method on a nil
+// receiver is a no-op — callers wire it unconditionally.
+func newAsyncDiagnostics(check func(context.Context, string) string, workspaceRoot string) *asyncDiagnostics {
+	if check == nil {
+		return nil
+	}
+	return &asyncDiagnostics{
+		check:         check,
+		workspaceRoot: workspaceRoot,
+		queued:        map[string]bool{},
+		results:       map[string]string{},
+	}
+}
+
+// enqueue schedules changed files for a background check. Paths are
+// workspace-relative from Result.ChangedFiles (absolute when under a granted
+// extra write root), mirroring SelfCorrector's resolution.
+func (diagnostics *asyncDiagnostics) enqueue(ctx context.Context, files []string) {
+	if diagnostics == nil || len(files) == 0 {
+		return
+	}
+	diagnostics.mu.Lock()
+	defer diagnostics.mu.Unlock()
+	for _, file := range files {
+		path := diagnostics.absPath(file)
+		if diagnostics.queued[path] {
+			continue
+		}
+		diagnostics.queued[path] = true
+		// A completed result for this file describes a pre-edit state now.
+		delete(diagnostics.results, path)
+		diagnostics.queue = append(diagnostics.queue, path)
+	}
+	if diagnostics.working == nil && len(diagnostics.queue) > 0 {
+		done := make(chan struct{})
+		diagnostics.working = done
+		go diagnostics.work(ctx, done)
+	}
+}
+
+func (diagnostics *asyncDiagnostics) work(ctx context.Context, done chan struct{}) {
+	defer close(done)
+	for {
+		diagnostics.mu.Lock()
+		if len(diagnostics.queue) == 0 || ctx.Err() != nil {
+			diagnostics.working = nil
+			diagnostics.mu.Unlock()
+			return
+		}
+		path := diagnostics.queue[0]
+		diagnostics.queue = diagnostics.queue[1:]
+		// Un-mark before checking so an edit that lands DURING the check
+		// re-enqueues the file and it is checked again in its final state.
+		delete(diagnostics.queued, path)
+		diagnostics.mu.Unlock()
+
+		block := diagnostics.check(ctx, path)
+
+		diagnostics.mu.Lock()
+		if block != "" {
+			diagnostics.results[path] = block
+		} else {
+			delete(diagnostics.results, path)
+		}
+		diagnostics.mu.Unlock()
+	}
+}
+
+// drain waits briefly for the worker to go quiet, then formats and consumes
+// all completed error blocks as one nudge. Returns "" when there is nothing
+// to report or the worker is still busy (results then surface next turn).
+func (diagnostics *asyncDiagnostics) drain(ctx context.Context) string {
+	return diagnostics.drainWithin(ctx, asyncDiagnosticsDrainTimeout)
+}
+
+// drainFinal is drain with the finalization budget: called before the run's
+// last model request, where an undelivered result would otherwise be lost.
+func (diagnostics *asyncDiagnostics) drainFinal(ctx context.Context) string {
+	return diagnostics.drainWithin(ctx, asyncDiagnosticsFinalDrainTimeout)
+}
+
+func (diagnostics *asyncDiagnostics) drainWithin(ctx context.Context, timeout time.Duration) string {
+	if diagnostics == nil {
+		return ""
+	}
+	diagnostics.mu.Lock()
+	busy := diagnostics.working
+	diagnostics.mu.Unlock()
+	if busy != nil {
+		timer := time.NewTimer(timeout)
+		defer timer.Stop()
+		select {
+		case <-busy:
+		case <-timer.C:
+			return ""
+		case <-ctx.Done():
+			return ""
+		}
+	}
+	diagnostics.mu.Lock()
+	defer diagnostics.mu.Unlock()
+	if len(diagnostics.results) == 0 {
+		return ""
+	}
+	paths := make([]string, 0, len(diagnostics.results))
+	for path := range diagnostics.results {
+		paths = append(paths, path)
+	}
+	sort.Strings(paths)
+	blocks := make([]string, 0, len(paths))
+	for _, path := range paths {
+		blocks = append(blocks, diagnostics.results[path])
+	}
+	diagnostics.results = map[string]string{}
+	return asyncDiagnosticsNudge + strings.Join(blocks, "\n")
+}
+
+func (diagnostics *asyncDiagnostics) absPath(path string) string {
+	if filepath.IsAbs(path) {
+		return path
+	}
+	return filepath.Join(diagnostics.workspaceRoot, path)
+}

internal/agent/async_diagnostics_test.go

@@ -0,0 +1,338 @@
+package agent
+
+import (
+	"context"
+	"path/filepath"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/Gitlawb/zero/internal/tools"
+	"github.com/Gitlawb/zero/internal/zeroruntime"
+)
+
+func TestAsyncDiagnosticsNilCollectorNoOps(t *testing.T) {
+	var diagnostics *asyncDiagnostics
+	if diagnostics != newAsyncDiagnostics(nil, "/ws") {
+		t.Fatal("nil check must yield a nil collector")
+	}
+	diagnostics.enqueue(context.Background(), []string{"a.go"})
+	if nudge := diagnostics.drain(context.Background()); nudge != "" {
+		t.Fatalf("nil collector drain = %q, want empty", nudge)
+	}
+}
+
+func TestAsyncDiagnosticsCollectsAndDrainsOnce(t *testing.T) {
+	// A real absolute root: a literal "/ws" is not filepath.IsAbs on Windows
+	// (no drive letter), which is exactly what the assertions below check.
+	root := t.TempDir()
+	var mu sync.Mutex
+	var checked []string
+	check := func(_ context.Context, absPath string) string {
+		mu.Lock()
+		checked = append(checked, absPath)
+		mu.Unlock()
+		if filepath.Base(absPath) == "clean.go" {
+			return ""
+		}
+		return "ERR " + filepath.Base(absPath)
+	}
+	diagnostics := newAsyncDiagnostics(check, root)
+	diagnostics.enqueue(context.Background(), []string{"broken.go", "clean.go"})
+
+	nudge := diagnostics.drain(context.Background())
+	if !strings.HasPrefix(nudge, asyncDiagnosticsNudge) {
+		t.Fatalf("nudge missing prefix: %q", nudge)
+	}
+	if !strings.Contains(nudge, "ERR broken.go") || strings.Contains(nudge, "clean.go") {
+		t.Fatalf("nudge = %q, want broken.go errors only", nudge)
+	}
+	mu.Lock()
+	for _, path := range checked {
+		if !filepath.IsAbs(path) || !strings.HasPrefix(path, root+string(filepath.Separator)) {
+			t.Fatalf("check received %q, want path under workspace root %q", path, root)
+		}
+	}
+	mu.Unlock()
+	if second := diagnostics.drain(context.Background()); second != "" {
+		t.Fatalf("second drain = %q, want empty (results are consumed)", second)
+	}
+}
+
+// A check still running at drain time defers delivery to the next drain
+// instead of blocking the turn.
+func TestAsyncDiagnosticsSlowCheckDefersToNextDrain(t *testing.T) {
+	previous := asyncDiagnosticsDrainTimeout
+	asyncDiagnosticsDrainTimeout = 20 * time.Millisecond
+	defer func() { asyncDiagnosticsDrainTimeout = previous }()
+
+	release := make(chan struct{})
+	check := func(_ context.Context, absPath string) string {
+		<-release
+		return "ERR " + filepath.Base(absPath)
+	}
+	diagnostics := newAsyncDiagnostics(check, "/ws")
+	diagnostics.enqueue(context.Background(), []string{"slow.go"})
+
+	start := time.Now()
+	if nudge := diagnostics.drain(context.Background()); nudge != "" {
+		t.Fatalf("drain during in-flight check = %q, want empty", nudge)
+	}
+	if elapsed := time.Since(start); elapsed > time.Second {
+		t.Fatalf("drain blocked %v, want bounded by the (shortened) timeout", elapsed)
+	}
+
+	close(release)
+	deadline := time.Now().Add(2 * time.Second)
+	for {
+		if nudge := diagnostics.drain(context.Background()); nudge != "" {
+			if !strings.Contains(nudge, "ERR slow.go") {
+				t.Fatalf("deferred nudge = %q", nudge)
+			}
+			return
+		}
+		if time.Now().After(deadline) {
+			t.Fatal("deferred diagnostics never delivered")
+		}
+		time.Sleep(5 * time.Millisecond)
+	}
+}
+
+// Re-enqueueing a file after its check completed replaces the stale result.
+func TestAsyncDiagnosticsReEditReplacesResult(t *testing.T) {
+	var mu sync.Mutex
+	response := "ERR old"
+	check := func(context.Context, string) string {
+		mu.Lock()
+		defer mu.Unlock()
+		return response
+	}
+	diagnostics := newAsyncDiagnostics(check, "/ws")
+
+	diagnostics.enqueue(context.Background(), []string{"a.go"})
+	waitForIdle(t, diagnostics)
+	mu.Lock()
+	response = "ERR new"
+	mu.Unlock()
+	diagnostics.enqueue(context.Background(), []string{"a.go"})
+
+	nudge := diagnostics.drain(context.Background())
+	if !strings.Contains(nudge, "ERR new") || strings.Contains(nudge, "ERR old") {
+		t.Fatalf("nudge = %q, want only the re-check result", nudge)
+	}
+}
+
+func waitForIdle(t *testing.T, diagnostics *asyncDiagnostics) {
+	t.Helper()
+	deadline := time.Now().Add(2 * time.Second)
+	for {
+		diagnostics.mu.Lock()
+		busy := diagnostics.working
+		diagnostics.mu.Unlock()
+		if busy == nil {
+			return
+		}
+		if time.Now().After(deadline) {
+			t.Fatal("worker never went idle")
+		}
+		time.Sleep(2 * time.Millisecond)
+	}
+}
+
+// changedFilesTool is a fake mutating tool reporting a changed file without
+// touching the filesystem.
+type changedFilesTool struct{}
+
+func (changedFilesTool) Name() string        { return "fake_edit" }
+func (changedFilesTool) Description() string { return "test mutating tool" }
+func (changedFilesTool) Parameters() tools.Schema {
+	return tools.Schema{Type: "object", Properties: map[string]tools.PropertySchema{}}
+}
+func (changedFilesTool) Safety() tools.Safety {
+	return tools.Safety{SideEffect: tools.SideEffectWrite, Permission: tools.PermissionAllow, Reason: "test"}
+}
+func (changedFilesTool) Run(context.Context, map[string]any) tools.Result {
+	return tools.Result{Status: tools.StatusOK, Output: "edited", ChangedFiles: []string{"main.go"}}
+}
+
+// End-to-end through Run: an edit turn does NOT carry diagnostics in the tool
+// result (the old inline path), but the next request contains the background
+// diagnostics nudge, before the model finalizes.
+func TestRunDeliversAsyncDiagnosticsNudgeNextTurn(t *testing.T) {
+	registry := tools.NewRegistry()
+	registry.Register(changedFilesTool{})
+	provider := &mockProvider{
+		turns: [][]zeroruntime.StreamEvent{
+			{
+				{Type: zeroruntime.StreamEventToolCallStart, ToolCallID: "call-1", ToolName: "fake_edit"},
+				{Type: zeroruntime.StreamEventToolCallDelta, ToolCallID: "call-1", ArgumentsFragment: `{}`},
+				{Type: zeroruntime.StreamEventToolCallEnd, ToolCallID: "call-1"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+			{
+				{Type: zeroruntime.StreamEventText, Content: "done"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+		},
+	}
+	root := t.TempDir()
+	var checkedPath string
+	var mu sync.Mutex
+
+	result, err := Run(context.Background(), "fix main.go", provider, Options{
+		Registry: registry,
+		Cwd:      root,
+		FileDiagnostics: func(_ context.Context, absPath string) string {
+			mu.Lock()
+			checkedPath = absPath
+			mu.Unlock()
+			return "main.go:1:1 error: boom"
+		},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if result.FinalAnswer != "done" {
+		t.Fatalf("final answer = %q", result.FinalAnswer)
+	}
+	if len(provider.requests) != 2 {
+		t.Fatalf("expected 2 provider turns, got %d", len(provider.requests))
+	}
+
+	// The tool result itself must NOT block on / embed diagnostics.
+	for _, message := range provider.requests[1].Messages {
+		if message.Role == zeroruntime.MessageRoleTool && strings.Contains(message.Content, "boom") {
+			t.Fatalf("diagnostics leaked into the tool result: %q", message.Content)
+		}
+	}
+	// The nudge must be present in the second request as a user message.
+	found := false
+	for _, message := range provider.requests[1].Messages {
+		if message.Role == zeroruntime.MessageRoleUser && strings.HasPrefix(message.Content, asyncDiagnosticsNudge) {
+			if !strings.Contains(message.Content, "boom") {
+				t.Fatalf("nudge missing diagnostics: %q", message.Content)
+			}
+			found = true
+		}
+	}
+	if !found {
+		t.Fatal("no async diagnostics nudge in the follow-up request")
+	}
+	mu.Lock()
+	defer mu.Unlock()
+	if want := filepath.Join(root, "main.go"); checkedPath != want {
+		t.Fatalf("checked path = %q, want %q", checkedPath, want)
+	}
+}
+
+// When the run hits the maxTurns ceiling right after an edit turn, the
+// final-answer request must still carry the diagnostics nudge — otherwise an
+// error introduced by the last edit would go unreported in the summary.
+func TestRunDrainsAsyncDiagnosticsBeforeMaxTurnsFinalAnswer(t *testing.T) {
+	registry := tools.NewRegistry()
+	registry.Register(changedFilesTool{})
+	provider := &mockProvider{
+		turns: [][]zeroruntime.StreamEvent{
+			{
+				{Type: zeroruntime.StreamEventToolCallStart, ToolCallID: "call-1", ToolName: "fake_edit"},
+				{Type: zeroruntime.StreamEventToolCallDelta, ToolCallID: "call-1", ArgumentsFragment: `{}`},
+				{Type: zeroruntime.StreamEventToolCallEnd, ToolCallID: "call-1"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+			{
+				{Type: zeroruntime.StreamEventText, Content: "summary"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+		},
+	}
+
+	result, err := Run(context.Background(), "fix main.go", provider, Options{
+		Registry: registry,
+		Cwd:      t.TempDir(),
+		MaxTurns: 1,
+		FileDiagnostics: func(context.Context, string) string {
+			return "main.go:1:1 error: boom"
+		},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if result.FinalAnswer != "summary" {
+		t.Fatalf("final answer = %q", result.FinalAnswer)
+	}
+	if len(provider.requests) != 2 {
+		t.Fatalf("expected the max-turns final-answer request, got %d requests", len(provider.requests))
+	}
+	found := false
+	for _, message := range provider.requests[1].Messages {
+		if message.Role == zeroruntime.MessageRoleUser && strings.HasPrefix(message.Content, asyncDiagnosticsNudge) {
+			found = true
+		}
+	}
+	if !found {
+		t.Fatal("max-turns final-answer request missing the diagnostics nudge")
+	}
+}
+
+// When the model finalizes while a slow check is still in flight (the
+// per-turn drain missed it), the finalization gate must wait it out and give
+// the model one more turn with the nudge instead of dropping the errors.
+func TestRunFinalizationGateDeliversLateDiagnostics(t *testing.T) {
+	previous := asyncDiagnosticsDrainTimeout
+	asyncDiagnosticsDrainTimeout = time.Millisecond
+	defer func() { asyncDiagnosticsDrainTimeout = previous }()
+
+	registry := tools.NewRegistry()
+	registry.Register(changedFilesTool{})
+	provider := &mockProvider{
+		turns: [][]zeroruntime.StreamEvent{
+			{
+				{Type: zeroruntime.StreamEventToolCallStart, ToolCallID: "call-1", ToolName: "fake_edit"},
+				{Type: zeroruntime.StreamEventToolCallDelta, ToolCallID: "call-1", ArgumentsFragment: `{}`},
+				{Type: zeroruntime.StreamEventToolCallEnd, ToolCallID: "call-1"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+			{
+				{Type: zeroruntime.StreamEventText, Content: "done"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+			{
+				{Type: zeroruntime.StreamEventText, Content: "done after fix"},
+				{Type: zeroruntime.StreamEventDone},
+			},
+		},
+	}
+
+	result, err := Run(context.Background(), "fix main.go", provider, Options{
+		Registry: registry,
+		Cwd:      t.TempDir(),
+		FileDiagnostics: func(context.Context, string) string {
+			// Slower than the (shortened) per-turn drain, well under the
+			// finalization budget.
+			time.Sleep(100 * time.Millisecond)
+			return "main.go:1:1 error: boom"
+		},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if result.FinalAnswer != "done after fix" {
+		t.Fatalf("final answer = %q, want the post-nudge answer", result.FinalAnswer)
+	}
+	if len(provider.requests) != 3 {
+		t.Fatalf("expected a third request carrying the late nudge, got %d requests", len(provider.requests))
+	}
+	found := false
+	for _, message := range provider.requests[2].Messages {
+		if message.Role == zeroruntime.MessageRoleUser && strings.HasPrefix(message.Content, asyncDiagnosticsNudge) {
+			if !strings.Contains(message.Content, "boom") {
+				t.Fatalf("nudge missing diagnostics: %q", message.Content)
+			}
+			found = true
+		}
+	}
+	if !found {
+		t.Fatal("finalization gate did not deliver the late diagnostics nudge")
+	}
+}

internal/agent/command_prefix.go

@@ -2,6 +2,7 @@ package agent
 
 import (
 	"fmt"
+	"runtime"
 	"strings"
 
 	"github.com/Gitlawb/zero/internal/sandbox"
@@ -27,10 +28,20 @@ func proposedCommandPrefix(toolName string, args map[string]any) []string {
 		}
 		return nil
 	}
-	for _, tokens := range segments {
-		if !knownSafeCommandSegment(tokens) && sandbox.ValidCommandPrefix(tokens) {
-			return append([]string(nil), tokens...)
+	// Only propose approving a prefix of one segment when every other segment
+	// in the command is independently known-safe. Once a prefix is approved,
+	// shellExecutionArgsForApproval escalates the whole command (every
+	// segment, not just the approved one) to bypass the sandbox, so offering a
+	// prefix that leaves an MSYS-prone (or otherwise unsafe) segment uncovered
+	// would let that segment run unsandboxed without ever being reviewed.
+	for index, tokens := range segments {
+		if knownSafeCommandSegment(tokens) {
+			continue
 		}
+		if !sandbox.ValidCommandPrefix(tokens) || !otherSegmentsKnownSafe(segments, index) {
+			return nil
+		}
+		return append([]string(nil), tokens...)
 	}
 	if len(segments) == 0 || !sandbox.ValidCommandPrefix(segments[0]) {
 		return nil
@@ -38,6 +49,20 @@ func proposedCommandPrefix(toolName string, args map[string]any) []string {
 	return append([]string(nil), segments[0]...)
 }
 
+// otherSegmentsKnownSafe reports whether every segment other than the one at
+// skip is known-safe on its own.
+func otherSegmentsKnownSafe(segments [][]string, skip int) bool {
+	for index, tokens := range segments {
+		if index == skip {
+			continue
+		}
+		if !knownSafeCommandSegment(tokens) {
+			return false
+		}
+	}
+	return true
+}
+
 func matchCommandPrefix(toolName string, args map[string]any, options Options) (sandbox.CommandPrefixGrant, bool, bool) {
 	if !isShellCommandTool(toolName) || options.Sandbox == nil {
 		return sandbox.CommandPrefixGrant{}, false, false
@@ -168,10 +193,6 @@ func cleanPrefixRule(prefix []string) []string {
 	return cleaned
 }
 
-func safeRequestedPrefix(prefix []string, command []string) bool {
-	return safeRequestedPrefixForSegments(prefix, [][]string{command})
-}
-
 func safeRequestedPrefixForSegments(prefix []string, segments [][]string) bool {
 	if len(prefix) == 0 || !sandbox.ValidCommandPrefix(prefix) {
 		return false
@@ -196,14 +217,6 @@ func safeRequestedPrefixForSegments(prefix []string, segments [][]string) bool {
 	return matched
 }
 
-func safeShellCommandTokens(command string) ([]string, bool) {
-	segments, ok := safeShellCommandSegments(command)
-	if !ok || len(segments) != 1 {
-		return nil, false
-	}
-	return segments[0], true
-}
-
 func safeShellCommandSegments(command string) ([][]string, bool) {
 	command = strings.TrimSpace(command)
 	if command == "" {
@@ -275,7 +288,11 @@ func knownSafeCommandSegment(command []string) bool {
 	if len(command) == 0 {
 		return false
 	}
-	switch commandName(command[0]) {
+	name := commandName(command[0])
+	if runtime.GOOS == "windows" && tools.MsysProneCommandName(name) {
+		return false
+	}
+	switch name {
 	case "cat", "cd", "cut", "echo", "expr", "false", "grep", "head", "id",
 		"ls", "nl", "paste", "pwd", "rev", "seq", "stat", "tail", "tr",
 		"true", "uname", "uniq", "wc", "which", "whoami":

internal/agent/command_prefix_test.go

@@ -1,9 +1,11 @@
 package agent
 
 import (
+	"runtime"
 	"testing"
 
 	"github.com/Gitlawb/zero/internal/sandbox"
+	"github.com/Gitlawb/zero/internal/tools"
 )
 
 func TestProposedCommandPrefixUsesSafeSimpleCommands(t *testing.T) {
@@ -35,12 +37,37 @@ func TestProposedCommandPrefixHonorsValidatedRequestedPrefix(t *testing.T) {
 
 func TestProposedCommandPrefixSupportsSegmentedCommands(t *testing.T) {
 	got := proposedCommandPrefix("bash", map[string]any{"command": "ps aux | head -5"})
+	if runtime.GOOS == "windows" {
+		// head is MSYS-prone on Windows (#458), so proposedCommandPrefix must
+		// not offer "ps aux" as a reusable prefix here: approving it would
+		// escalate the whole command, including the uncovered head segment,
+		// to bypass the sandbox unreviewed. See
+		// TestProposedCommandPrefixRejectsPrefixLeavingUnsafeTailUncovered for
+		// the platform-independent regression coverage of this behavior.
+		if got != nil {
+			t.Fatalf("expected no prefix on Windows because head is MSYS-prone, got %#v", got)
+		}
+		return
+	}
 	want := []string{"ps", "aux"}
 	if !equalStringSlices(got, want) {
 		t.Fatalf("prefix = %#v, want %#v", got, want)
 	}
 }
 
+// TestProposedCommandPrefixRejectsPrefixLeavingUnsafeTailUncovered guards
+// against proposedCommandPrefix offering to approve one segment of a
+// multi-segment command (e.g. "ps aux") while a different segment (e.g. "npm
+// install") is not known-safe. shellExecutionArgsForApproval escalates the
+// entire command once any prefix is approved, so an uncovered unsafe segment
+// would bypass the sandbox unreviewed. Uses npm, which is never known-safe on
+// any platform, so the assertion does not depend on runtime.GOOS.
+func TestProposedCommandPrefixRejectsPrefixLeavingUnsafeTailUncovered(t *testing.T) {
+	if got := proposedCommandPrefix("bash", map[string]any{"command": "ps aux && npm install"}); got != nil {
+		t.Fatalf("expected no prefix because npm segment is not known-safe, got %#v", got)
+	}
+}
+
 func TestProposedCommandPrefixHonorsRequestedPrefixAcrossSegments(t *testing.T) {
 	got := proposedCommandPrefix("bash", map[string]any{
 		"command":     "git status --short && git status --branch",
@@ -120,13 +147,35 @@ func TestProposedCommandPrefixRejectsUnsafeLaunchers(t *testing.T) {
 func TestMatchCommandPrefixCoversSegmentedCommandWithSafeTail(t *testing.T) {
 	engine := sandbox.NewEngine(sandbox.EngineOptions{WorkspaceRoot: t.TempDir()})
 	engine.GrantCommandPrefixForSession("bash", []string{"ps", "aux"})
+	// head is MSYS-prone on Windows (#458) and must not count as a known-safe tail.
+	command := "ps aux | head -5"
+	if runtime.GOOS == "windows" {
+		command = "ps aux | echo ok"
+	}
 
-	grant, ok, session := matchCommandPrefix("bash", map[string]any{"command": "ps aux | head -5"}, Options{Sandbox: engine})
+	grant, ok, session := matchCommandPrefix("bash", map[string]any{"command": command}, Options{Sandbox: engine})
 	if !ok || !session || !equalStringSlices(grant.Prefix, []string{"ps", "aux"}) {
 		t.Fatalf("match = %#v ok=%v session=%v, want session ps aux prefix", grant, ok, session)
 	}
 }
 
+func TestKnownSafeCommandSegmentRejectsMsysProneOnWindows(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		t.Skip("windows-only known-safe MSYS guard")
+	}
+	for _, command := range [][]string{{"head", "-5"}, {"cat", "file.txt"}, {"grep", "pat"}} {
+		if knownSafeCommandSegment(command) {
+			t.Fatalf("expected %q to be unsafe on Windows, got known-safe", command)
+		}
+	}
+	if !knownSafeCommandSegment([]string{"echo", "ok"}) {
+		t.Fatal("expected echo to remain known-safe on Windows")
+	}
+	if !tools.MsysProneCommandName("head") {
+		t.Fatal("expected head to be MSYS-prone")
+	}
+}
+
 func TestMatchCommandPrefixRejectsUncoveredSegment(t *testing.T) {
 	engine := sandbox.NewEngine(sandbox.EngineOptions{WorkspaceRoot: t.TempDir()})
 	engine.GrantCommandPrefixForSession("bash", []string{"ps", "aux"})

internal/agent/loop.go

@@ -137,6 +137,12 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 	guards := newGuardState()
 	compactor := newCompactionState(options)
 
+	// Background post-edit diagnostics: files changed by mutating tools are
+	// checked off the tool-call critical path and any errors are appended as a
+	// nudge before the NEXT request (see async_diagnostics.go). nil when no
+	// FileDiagnostics callback is wired; every method no-ops on nil.
+	postEditDiagnostics := newAsyncDiagnostics(options.FileDiagnostics, options.Cwd)
+
 	// loaded tracks deferred-eligible tools the model has pulled via tool_search
 	// during THIS run. It is consulted by partitionTools each turn to expose a
 	// loaded tool's full schema; it lives only for the run (v1 within-run scope).
@@ -159,6 +165,17 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 	for turn := 0; turn < maxTurns; turn++ {
 		result.Turns = turn + 1
 
+		// Deliver background post-edit diagnostics from the previous turn's edits
+		// BEFORE compaction so the nudge is part of the request being budgeted.
+		// A brief wait at most (asyncDiagnosticsDrainTimeout); an unfinished check
+		// simply delivers on a later turn.
+		if nudge := postEditDiagnostics.drain(ctx); nudge != "" {
+			messages = append(messages, zeroruntime.Message{
+				Role:    zeroruntime.MessageRoleUser,
+				Content: nudge,
+			})
+		}
+
 		// Build the per-turn tool list first so proactive compaction can include
 		// the tool-definition tokens (they ride on every request) in its estimate.
 		// partitionTools depends only on registry/permissions/options/loaded, not on
@@ -474,6 +491,19 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 					continue
 				}
 			}
+			// Finalization diagnostics gate: edits from this run may still have
+			// checks in flight — the per-turn drain waits only briefly and defers
+			// to "a later turn", but a final answer means there is no later turn.
+			// Wait out the full inline-era budget once; an introduced error gives
+			// the model one more turn to see (and fix) it instead of being lost.
+			// Free for runs that never edited: an idle collector returns "".
+			if nudge := postEditDiagnostics.drainFinal(ctx); nudge != "" {
+				messages = append(messages, zeroruntime.Message{
+					Role:    zeroruntime.MessageRoleUser,
+					Content: nudge,
+				})
+				continue
+			}
 			result.FinalAnswer = collected.Text
 			result.Messages = copyMessages(messages)
 			return result, nil
@@ -590,11 +620,14 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 				failureHint = toolFailureHint(call.Name, toolSchemaJSON(registry, call.Name), toolResult.Output)
 			}
 
-			// Post-edit self-correction: collect the files this successful mutating
-			// tool changed; verification runs once over the union after the batch.
-			// A read-only tool (no ChangedFiles) never contributes.
-			if options.SelfCorrect != nil && toolResult.Status == tools.StatusOK && len(toolResult.ChangedFiles) > 0 {
+			// Collect the files this successful mutating tool changed. Self-correct
+			// verification runs once over the union after the batch; background
+			// diagnostics start NOW so the language server analyzes while the rest
+			// of the batch executes. A read-only tool (no ChangedFiles) never
+			// contributes.
+			if toolResult.Status == tools.StatusOK && len(toolResult.ChangedFiles) > 0 {
 				changedFilesThisBatch = append(changedFilesThisBatch, toolResult.ChangedFiles...)
+				postEditDiagnostics.enqueue(ctx, toolResult.ChangedFiles)
 			}
 		}
 
@@ -677,6 +710,17 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 	// mid-run, not a natural completion (a finished run returns via the no-tool-call
 	// success path before this). Under the headless completion gate that is INCOMPLETE,
 	// not success, so a run that loops to the turn limit isn't reported as done.
+	//
+	// The final-answer call is one more model request, so diagnostics from the
+	// LAST turn's edits get a drain too — with the finalization budget, since
+	// there is no later turn to defer to — otherwise an error introduced by
+	// the final edit would go unreported in the summary.
+	if nudge := postEditDiagnostics.drainFinal(ctx); nudge != "" {
+		messages = append(messages, zeroruntime.Message{
+			Role:    zeroruntime.MessageRoleUser,
+			Content: nudge,
+		})
+	}
 	if answer, finalMessages, finishReason := finalAnswerAfterMaxTurns(ctx, provider, messages, options); strings.TrimSpace(answer) != "" {
 		result.FinalAnswer = answer
 		result.FinishReason = finishReason
@@ -1100,8 +1144,12 @@ func executeToolCall(ctx context.Context, registry *tools.Registry, call ToolCal
 		// Per-session file version tracker so write_file/edit_file refuse to clobber
 		// a file that changed on disk outside Zero since it was last read.
 		FileTracker: options.FileTracker,
-		// Inline post-edit diagnostics for mutating tools (nil = disabled).
-		Diagnostics: options.FileDiagnostics,
+		// Post-edit diagnostics are NOT forwarded to the tools: they used to run
+		// synchronously inside edit_file/write_file and block every mutating tool
+		// call on the language server (≥300ms debounce floor, 10s cap). The loop
+		// now checks changed files in the background and nudges the model before
+		// its next request instead (see async_diagnostics.go). The tools' inline
+		// mechanism (tools.RunOptions.Diagnostics) stays for direct API callers.
 		// Forward the run's operator tool filters so a filter-aware tool
 		// (tool_search) never discloses or loads an operator-hidden deferred tool.
 		EnabledTools:  options.EnabledTools,

internal/agent/loop_test.go

@@ -4,6 +4,7 @@ import (
 	"context"
 	"encoding/json"
 	"errors"
+	"fmt"
 	"os"
 	"path/filepath"
 	"runtime"
@@ -1945,6 +1946,11 @@ func TestRunCommandPrefixApprovalBypassesSandboxForMatchingShellCalls(t *testing
 
 func TestRunCommandPrefixApprovalCoversSegmentedShellWithSafeTail(t *testing.T) {
 	root := t.TempDir()
+	segmentedCommand := `ps aux | head -5`
+	if runtime.GOOS == "windows" {
+		// head is MSYS-prone on Windows (#458) and no longer counts as a known-safe tail.
+		segmentedCommand = `ps aux | echo ok`
+	}
 	retryTool := &sandboxDeniedRetryTool{}
 	registry := tools.NewRegistry()
 	registry.Register(retryTool)
@@ -1958,7 +1964,7 @@ func TestRunCommandPrefixApprovalCoversSegmentedShellWithSafeTail(t *testing.T)
 			},
 			{
 				{Type: zeroruntime.StreamEventToolCallStart, ToolCallID: "call-2", ToolName: "bash"},
-				{Type: zeroruntime.StreamEventToolCallDelta, ToolCallID: "call-2", ArgumentsFragment: `{"command":"ps aux | head -5"}`},
+				{Type: zeroruntime.StreamEventToolCallDelta, ToolCallID: "call-2", ArgumentsFragment: fmt.Sprintf(`{"command":%q}`, segmentedCommand)},
 				{Type: zeroruntime.StreamEventToolCallEnd, ToolCallID: "call-2"},
 				{Type: zeroruntime.StreamEventDone},
 			},
@@ -2907,8 +2913,10 @@ func TestBuildSystemPromptInjectsHostShellContext(t *testing.T) {
 		t.Fatalf("expected operating system in environment block, got %q", prompt)
 	}
 	if runtime.GOOS == "windows" {
-		if !strings.Contains(prompt, "Windows cmd.exe syntax") || !strings.Contains(prompt, "cwd argument") {
-			t.Fatalf("expected Windows cmd.exe shell guidance in prompt, got %q", prompt)
+		for _, want := range []string{"Windows cmd.exe syntax", "cwd argument", "MSYS binaries", "grep", "require_escalated"} {
+			if !strings.Contains(prompt, want) {
+				t.Fatalf("expected Windows shell guidance to mention %q, got %q", want, prompt)
+			}
 		}
 	} else if !strings.Contains(prompt, "/bin/sh syntax") {
 		t.Fatalf("expected POSIX shell guidance in prompt, got %q", prompt)

internal/agent/partition_cache_stable_test.go

@@ -34,7 +34,7 @@ func TestPartitionToolsActiveAppendsLoadedToolAfterEagerBlock(t *testing.T) {
 		t.Fatalf("expected read_file, tool_search and loaded alpha all exposed, got %#v", exposed)
 	}
 	// The eager tools must precede the loaded deferred tool (appended, not inserted).
-	if !(readPos < alphaPos && searchPos < alphaPos) {
+	if readPos >= alphaPos || searchPos >= alphaPos {
 		t.Fatalf("loaded deferred tool must be appended after the eager block; got read=%d search=%d alpha=%d", readPos, searchPos, alphaPos)
 	}
 	// beta was never loaded — it stays hidden.

internal/agent/skills_context_test.go

@@ -7,14 +7,18 @@ import (
 )
 
 func TestSkillsContextCapsLongList(t *testing.T) {
-	skills := make([]SkillInfo, 0, 40)
-	for i := 0; i < 40; i++ {
+	// 60 skills with realistic trigger-rich descriptions (~180 chars each, under
+	// the 200-rune truncation) total well past the 4096-byte list budget, so the
+	// overflow summary must kick in while the block stays bounded.
+	longDesc := strings.Repeat("use when the request touches deployments, release notes, or verification; ", 2) + "number "
+	skills := make([]SkillInfo, 0, 60)
+	for i := 0; i < 60; i++ {
 		n := strconv.Itoa(i)
-		skills = append(skills, SkillInfo{Name: "skill-" + n, Description: "does something useful, number " + n})
+		skills = append(skills, SkillInfo{Name: "skill-" + n, Description: longDesc + n})
 	}
 	got := skillsContext(Options{Skills: skills})
-	if len(got) > 1200 {
-		t.Fatalf("skills block should stay bounded, got %d bytes:\n%s", len(got), got)
+	if len(got) > skillsContextListBudget+1000 {
+		t.Fatalf("skills block should stay bounded near the %d-byte budget, got %d bytes:\n%s", skillsContextListBudget, len(got), got)
 	}
 	if !strings.Contains(got, "more (call skill") {
 		t.Fatalf("expected an overflow summary line, got:\n%s", got)
@@ -25,6 +29,27 @@ func TestSkillsContextCapsLongList(t *testing.T) {
 	}
 }
 
+// A realistic mid-size skill set (20 skills, trigger-rich descriptions) must be
+// listed in FULL — no overflow summary. This pins the fix for the old 640-byte
+// budget, under which skills past ~#6 were invisible to the model and therefore
+// never triggered.
+func TestSkillsContextListsRealisticSetInFull(t *testing.T) {
+	desc := "Use when the user asks about deployments, release notes, or pre-merge verification runs."
+	skills := make([]SkillInfo, 0, 20)
+	for i := 0; i < 20; i++ {
+		skills = append(skills, SkillInfo{Name: "skill-" + strconv.Itoa(i), Description: desc})
+	}
+	got := skillsContext(Options{Skills: skills})
+	if strings.Contains(got, "more (call skill") {
+		t.Fatalf("20 described skills must all be listed without overflow, got:\n%s", got)
+	}
+	for i := 0; i < 20; i++ {
+		if !strings.Contains(got, "- skill-"+strconv.Itoa(i)+":") {
+			t.Fatalf("skill-%d missing from the list:\n%s", i, got)
+		}
+	}
+}
+
 func TestSkillsContext(t *testing.T) {
 	if got := skillsContext(Options{}); got != "" {
 		t.Fatalf("no skills should yield an empty section, got %q", got)

internal/agent/system_prompt.go

@@ -191,10 +191,19 @@ func specialistDelegationContext(options Options) string {
 // when no skills are installed, so a skill-less run reproduces the previous prompt
 // byte-for-byte.
 // skillsContextListBudget bounds the bytes spent listing individual skills so a
-// workspace with dozens of them can't bloat every turn's prompt. Skills past the
-// budget are summarized as a count rather than dropped — the model can still load
-// any of them by name (an unknown name returns the full list from the skill tool).
-const skillsContextListBudget = 640
+// workspace with an extreme number of them can't bloat every turn's prompt.
+// Skills past the budget are summarized as a count rather than dropped — the
+// model can still load any of them by name (an unknown name returns the full
+// list from the skill tool).
+//
+// The budget is deliberately generous — roughly 18 skills with maximally long
+// (200-rune, ASCII) descriptions, or 40+ with typical terser ones; non-ASCII
+// descriptions consume it faster since the budget counts bytes. This list is
+// the model's ONLY discovery surface, so a skill squeezed out of it effectively
+// never triggers. The previous 640-byte cap silently broke invocation for
+// anyone with more than ~6 skills — the model cannot match a request against a
+// skill it cannot see.
+const skillsContextListBudget = 4096
 
 func skillsContext(options Options) string {
 	if len(options.Skills) == 0 {
@@ -202,7 +211,7 @@ func skillsContext(options Options) string {
 	}
 	var b strings.Builder
 	b.WriteString("<available_skills>\n")
-	b.WriteString("Reusable, on-demand instruction sets you can load with the skill tool. When a request matches one, call skill with its exact name to pull in its guidance before acting — do not guess names or skip a relevant skill.\n")
+	b.WriteString("Reusable, on-demand instruction sets you can load with the skill tool. Before acting on a request, scan this list; when the request matches a skill's name or description, call skill with its exact name FIRST and follow the loaded guidance — do not guess names, do not skip a matching skill, and do not substitute your own approach for its instructions.\n")
 	listed, spent, omitted := 0, 0, 0
 	for _, info := range options.Skills {
 		name := strings.TrimSpace(info.Name)
@@ -232,9 +241,11 @@ func skillsContext(options Options) string {
 }
 
 // truncateForSkillLine keeps a skill's one-line description short so a single
-// verbose description can't dominate the skills-list budget.
+// verbose description can't dominate the skills-list budget. The cap is roomy on
+// purpose: the description carries the skill's trigger conditions ("use when…"),
+// and truncating those is what stops the model from ever invoking the skill.
 func truncateForSkillLine(desc string) string {
-	const maxDescRunes = 100
+	const maxDescRunes = 200
 	runes := []rune(desc)
 	if len(runes) <= maxDescRunes {
 		return desc
@@ -275,7 +286,7 @@ func workspaceContext(cwd string) string {
 	b.WriteString("Working directory: " + cwd + "\n")
 	b.WriteString("Operating system: " + runtime.GOOS + "\n")
 	if runtime.GOOS == "windows" {
-		b.WriteString("Shell syntax: Windows cmd.exe syntax for exec_command/bash tools; prefer the workdir/cwd argument instead of cd when changing directories.\n")
+		b.WriteString("Shell syntax: Windows cmd.exe syntax for exec_command/bash tools; prefer the workdir/cwd argument instead of cd when changing directories. Do not pipe to or invoke POSIX coreutils from Git for Windows (usr\\bin head/grep/tail/cat/...): they are MSYS binaries and fail under the write-restricted sandbox; use native Zero tools (grep, read_file, list_directory, glob) or cmd.exe findstr/more instead, or sandbox_permissions require_escalated only when host-level execution is truly required.\n")
 	} else {
 		b.WriteString("Shell syntax: /bin/sh syntax for exec_command/bash tools; prefer the workdir/cwd argument instead of cd when changing directories.\n")
 	}

internal/agent/types.go

@@ -285,11 +285,13 @@ type Options struct {
 	// ceiling and the autonomy gate. nil disables it entirely (the loop is
 	// byte-identical to before). One instance per run — it holds attempt state.
 	SelfCorrect *SelfCorrector
-	// FileDiagnostics, when set, is passed to mutating tools so edit_file /
-	// write_file append error-severity language diagnostics for the file they
-	// just wrote directly to their tool output — the model sees an error it
-	// introduced in the same turn instead of a later verification pass. Build
-	// one with NewFileDiagnostics. nil disables inline diagnostics.
+	// FileDiagnostics, when set, checks files changed by mutating tools for
+	// error-severity language diagnostics IN THE BACKGROUND and appends any
+	// errors as a nudge before the model's next request — the model still sees
+	// an error it introduced at its next decision point, but no tool call ever
+	// blocks on the language server (the old inline path stalled every edit on
+	// a ≥300ms debounce, 10s cap). Build one with NewFileDiagnostics. nil
+	// disables post-edit diagnostics.
 	FileDiagnostics func(ctx context.Context, absPath string) string
 
 	// RequireCompletionSignal gates run completion for HEADLESS exec. Without it,

internal/cli/app.go

@@ -12,6 +12,7 @@ import (
 	"os/exec"
 	"path/filepath"
 	"strings"
+	"sync"
 	"time"
 
 	"github.com/Gitlawb/zero/internal/agent"
@@ -782,6 +783,14 @@ func runInteractiveTUIWithSetup(stderr io.Writer, deps appDeps, permissionMode a
 			Specialists:    specialistRuntime.specialists,
 			Skills:         pluginActivation.skillInfos(deps.skillsDir()),
 		},
+		// LoadSkills backs /skills and direct /<skill-name> invocation in the TUI.
+		// It resolves against the same merged set (default dir + plugin skill
+		// roots) as the skill tool and the system-prompt list, re-read per use so
+		// newly installed skills work without a restart.
+		LoadSkills: cachedSkillsLoader(func() []skills.Skill {
+			merged, _ := plugins.MergedSkillsLoaded(deps.skillsDir(), pluginActivation.skillRoots)
+			return merged
+		}),
 		PermissionMode: permissionMode,
 		Notify:         resolved.Notify,
 		KeyBindings:    resolved.KeyBindings,
@@ -1277,3 +1286,26 @@ Flags:
 `)
 	return err
 }
+
+// cachedSkillsLoader memoizes a skills loader for a short interval. The TUI
+// calls the loader from autocomplete on every "/x" keystroke; without a cache
+// each keystroke would re-read every SKILL.md body. Two seconds is fresh enough
+// that a newly installed skill still shows up "immediately" while typing.
+func cachedSkillsLoader(load func() []skills.Skill) func() []skills.Skill {
+	var (
+		mu     sync.Mutex
+		at     time.Time
+		cached []skills.Skill
+	)
+	const ttl = 2 * time.Second
+	return func() []skills.Skill {
+		mu.Lock()
+		defer mu.Unlock()
+		if cached != nil && time.Since(at) < ttl {
+			return cached
+		}
+		cached = load()
+		at = time.Now()
+		return cached
+	}
+}

internal/cli/exec.go

@@ -711,9 +711,10 @@ func runExec(args []string, stdout io.Writer, stderr io.Writer, deps appDeps) in
 // sessions); it is a no-op when self-correct is off.
 func newExecSelfCorrector(enabled bool, workspaceRoot string, autonomy string) (*agent.SelfCorrector, func(context.Context, string) string, func()) {
 	// The manager is created regardless of --self-correct: it also backs the
-	// always-on inline post-edit diagnostics (agent.NewFileDiagnostics), and it
-	// stays lazy — no language server is spawned unless an edited file's
-	// language actually has one installed on PATH.
+	// always-on background post-edit diagnostics (agent.NewFileDiagnostics,
+	// collected off the tool-call path by the loop), and it stays lazy — no
+	// language server is spawned unless an edited file's language actually has
+	// one installed on PATH.
 	manager := lsp.NewManager(workspaceRoot)
 	cleanup := func() {
 		ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)

internal/sessions/append_events_test.go

@@ -0,0 +1,233 @@
+package sessions
+
+import (
+	"encoding/json"
+	"fmt"
+	"reflect"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+)
+
+func TestStoreAppendEventsBatchesSequencesAndMetadata(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: sequenceClock([]time.Time{
+		time.Date(2026, 6, 4, 15, 0, 0, 0, time.UTC),
+		time.Date(2026, 6, 4, 15, 0, 1, 0, time.UTC),
+		time.Date(2026, 6, 4, 15, 0, 2, 0, time.UTC),
+		time.Date(2026, 6, 4, 15, 0, 3, 0, time.UTC),
+	})})
+	session, err := store.Create(CreateInput{SessionID: "batch"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+
+	appended, err := store.AppendEvents(session.SessionID, []AppendEventInput{
+		{Type: EventMessage, Payload: map[string]any{"role": "user", "content": "one"}},
+		{Type: EventToolCall, Payload: map[string]any{"id": "call_1", "name": "read_file"}},
+		{Type: EventToolResult, Payload: map[string]any{"toolCallId": "call_1", "status": "ok"}},
+	})
+	if err != nil {
+		t.Fatalf("AppendEvents returned error: %v", err)
+	}
+	if len(appended) != 3 {
+		t.Fatalf("expected 3 appended events, got %#v", appended)
+	}
+	for index, event := range appended {
+		wantSequence := index + 1
+		if event.Sequence != wantSequence || event.ID != fmt.Sprintf("batch:%d", wantSequence) {
+			t.Fatalf("event identity mismatch at %d: %#v", index, event)
+		}
+	}
+	if appended[0].CreatedAt != "2026-06-04T15:00:01Z" || appended[2].CreatedAt != "2026-06-04T15:00:03Z" {
+		t.Fatalf("unexpected event timestamps: %#v", appended)
+	}
+
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || loaded.EventCount != 3 || loaded.LastEventType != EventToolResult || loaded.UpdatedAt != appended[2].CreatedAt {
+		t.Fatalf("metadata not updated from final batch event: %#v", loaded)
+	}
+	events, err := store.ReadEvents(session.SessionID)
+	if err != nil {
+		t.Fatalf("ReadEvents returned error: %v", err)
+	}
+	if !reflect.DeepEqual(eventTypesForTest(events), []EventType{EventMessage, EventToolCall, EventToolResult}) {
+		t.Fatalf("unexpected event types: %#v", events)
+	}
+}
+
+func TestStoreAppendEventsEmptyBatchDoesNotRewriteMetadata(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: fixedClock("2026-06-04T15:10:00Z")})
+	session, err := store.Create(CreateInput{SessionID: "empty_batch", Title: "unchanged"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+
+	appended, err := store.AppendEvents(session.SessionID, nil)
+	if err != nil {
+		t.Fatalf("AppendEvents empty returned error: %v", err)
+	}
+	if len(appended) != 0 {
+		t.Fatalf("empty AppendEvents returned %#v", appended)
+	}
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || !reflect.DeepEqual(*loaded, session) {
+		t.Fatalf("empty AppendEvents rewrote metadata: before=%#v after=%#v", session, loaded)
+	}
+}
+
+func TestStoreAppendEventsInvalidPayloadDoesNotPartiallyAppend(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: fixedClock("2026-06-04T15:20:00Z")})
+	session, err := store.Create(CreateInput{SessionID: "invalid_batch"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+
+	_, err = store.AppendEvents(session.SessionID, []AppendEventInput{
+		{Type: EventMessage, Payload: map[string]any{"content": "valid first"}},
+		{Type: EventMessage, Payload: json.RawMessage(`{"broken"`)},
+	})
+	if err == nil || !strings.Contains(err.Error(), "invalid raw JSON payload") {
+		t.Fatalf("expected invalid raw payload error, got %v", err)
+	}
+	events, err := store.ReadEvents(session.SessionID)
+	if err != nil {
+		t.Fatalf("ReadEvents returned error: %v", err)
+	}
+	if len(events) != 0 {
+		t.Fatalf("invalid batch should not append partial events: %#v", events)
+	}
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || loaded.EventCount != 0 || loaded.LastEventType != "" {
+		t.Fatalf("invalid batch should not update metadata: %#v", loaded)
+	}
+}
+
+func TestStoreAppendEventsSequencesAfterMetadataLag(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: fixedClock("2026-06-04T15:30:00Z")})
+	session, err := store.Create(CreateInput{SessionID: "lagging"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+	if _, err := store.AppendEvent(session.SessionID, AppendEventInput{Type: EventMessage, Payload: map[string]any{"content": "already durable"}}); err != nil {
+		t.Fatalf("AppendEvent returned error: %v", err)
+	}
+	lagging, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	lagging.EventCount = 0
+	lagging.LastEventType = ""
+	if err := store.writeMetadata(*lagging); err != nil {
+		t.Fatalf("writeMetadata returned error: %v", err)
+	}
+
+	appended, err := store.AppendEvents(session.SessionID, []AppendEventInput{
+		{Type: EventToolCall, Payload: map[string]any{"id": "call"}},
+		{Type: EventToolResult, Payload: map[string]any{"toolCallId": "call"}},
+	})
+	if err != nil {
+		t.Fatalf("AppendEvents returned error: %v", err)
+	}
+	if len(appended) != 2 || appended[0].Sequence != 2 || appended[1].Sequence != 3 {
+		t.Fatalf("batch did not sequence after durable log tail: %#v", appended)
+	}
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || loaded.EventCount != 3 || loaded.LastEventType != EventToolResult {
+		t.Fatalf("metadata not repaired by batch append: %#v", loaded)
+	}
+}
+
+func TestStoreAppendEventsSerializesConcurrentBatches(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: fixedClock("2026-06-04T15:40:00Z")})
+	session, err := store.Create(CreateInput{SessionID: "concurrent_batches"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+
+	const writers = 8
+	const perBatch = 3
+	var wg sync.WaitGroup
+	errs := make(chan error, writers)
+	for writer := 0; writer < writers; writer++ {
+		wg.Add(1)
+		go func(writer int) {
+			defer wg.Done()
+			appended, err := store.AppendEvents(session.SessionID, []AppendEventInput{
+				{Type: EventMessage, Payload: map[string]int{"writer": writer, "index": 0}},
+				{Type: EventMessage, Payload: map[string]int{"writer": writer, "index": 1}},
+				{Type: EventMessage, Payload: map[string]int{"writer": writer, "index": 2}},
+			})
+			if err != nil {
+				errs <- err
+				return
+			}
+			if len(appended) != perBatch {
+				errs <- fmt.Errorf("writer %d appended %d events", writer, len(appended))
+				return
+			}
+			for index := 1; index < len(appended); index++ {
+				if appended[index].Sequence != appended[index-1].Sequence+1 {
+					errs <- fmt.Errorf("writer %d batch was interleaved: %#v", writer, appended)
+					return
+				}
+			}
+			errs <- nil
+		}(writer)
+	}
+	wg.Wait()
+	close(errs)
+	for err := range errs {
+		if err != nil {
+			t.Fatalf("AppendEvents returned error: %v", err)
+		}
+	}
+
+	events, err := store.ReadEvents(session.SessionID)
+	if err != nil {
+		t.Fatalf("ReadEvents returned error: %v", err)
+	}
+	total := writers * perBatch
+	if len(events) != total {
+		t.Fatalf("expected %d events, got %d", total, len(events))
+	}
+	seen := map[int]bool{}
+	for _, event := range events {
+		if seen[event.Sequence] {
+			t.Fatalf("duplicate sequence %d in %#v", event.Sequence, events)
+		}
+		seen[event.Sequence] = true
+	}
+	for sequence := 1; sequence <= total; sequence++ {
+		if !seen[sequence] {
+			t.Fatalf("missing sequence %d in %#v", sequence, events)
+		}
+	}
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || loaded.EventCount != total || loaded.LastEventType != EventMessage {
+		t.Fatalf("metadata not updated after concurrent batches: %#v", loaded)
+	}
+}
+
+func eventTypesForTest(events []Event) []EventType {
+	types := make([]EventType, 0, len(events))
+	for _, event := range events {
+		types = append(types, event.Type)
+	}
+	return types
+}

internal/sessions/store.go

@@ -153,6 +153,11 @@ type AppendEventInput struct {
 	Payload any
 }
 
+type preparedAppendEvent struct {
+	Type    EventType
+	Payload json.RawMessage
+}
+
 type RecordSpecInput struct {
 	SpecID              string
 	SpecFilePath        string
@@ -426,7 +431,7 @@ func (store *Store) Fork(parentSessionID string, input ForkInput) (Metadata, err
 	if err != nil {
 		return Metadata{}, err
 	}
-	copied := 0
+	copyInputs := []AppendEventInput{}
 	for _, event := range events {
 		// Do NOT copy usage accounting into the fork. It already counted against the
 		// parent, and a usage report that aggregates the parent and the fork would
@@ -435,11 +440,12 @@ func (store *Store) Fork(parentSessionID string, input ForkInput) (Metadata, err
 		if event.Type == EventUsage {
 			continue
 		}
-		if _, err := store.AppendEvent(fork.SessionID, AppendEventInput{Type: event.Type, Payload: event.Payload}); err != nil {
-			return Metadata{}, err
-		}
-		copied++
+		copyInputs = append(copyInputs, AppendEventInput{Type: event.Type, Payload: event.Payload})
 	}
+	if _, err := store.AppendEvents(fork.SessionID, copyInputs); err != nil {
+		return Metadata{}, err
+	}
+	copied := len(copyInputs)
 	// Copy the parent's content-addressed checkpoint blobs into the fork so the
 	// copied EventSessionCheckpoint events resolve to real blobs and a rewind on
 	// the fork can restore file content (otherwise rewind reads missing blobs
@@ -513,19 +519,34 @@ func (store *Store) RecordSpec(sessionID string, input RecordSpecInput) (Metadat
 }
 
 func (store *Store) AppendEvent(sessionID string, input AppendEventInput) (Event, error) {
-	if !ValidSessionID(sessionID) {
-		return Event{}, fmt.Errorf("invalid zero session id %q", sessionID)
-	}
-	if strings.TrimSpace(string(input.Type)) == "" {
-		return Event{}, fmt.Errorf("zero session event type is required")
-	}
-	unlock, err := store.lockSession(sessionID)
+	events, err := store.AppendEvents(sessionID, []AppendEventInput{input})
 	if err != nil {
 		return Event{}, err
 	}
+	return events[0], nil
+}
+
+// AppendEvents appends a batch of events atomically under one session lock and
+// durability pass. The returned events have contiguous sequences in input order.
+// An empty batch is a no-op and does not rewrite metadata.
+func (store *Store) AppendEvents(sessionID string, inputs []AppendEventInput) ([]Event, error) {
+	if !ValidSessionID(sessionID) {
+		return nil, fmt.Errorf("invalid zero session id %q", sessionID)
+	}
+	prepared, err := prepareAppendEventInputs(inputs)
+	if err != nil {
+		return nil, err
+	}
+	if len(prepared) == 0 {
+		return []Event{}, nil
+	}
+	unlock, err := store.lockSession(sessionID)
+	if err != nil {
+		return nil, err
+	}
 	defer unlock()
 
-	return store.appendEventLocked(sessionID, input)
+	return store.appendPreparedEventsLocked(sessionID, prepared)
 }
 
 // AppendEventUnlessExists appends input only when exists(currentEvents) is false,
@@ -572,14 +593,27 @@ func (store *Store) AppendEventUnlessExists(sessionID string, input AppendEventI
 // the single lock they already hold, instead of re-locking (which would deadlock
 // on the non-reentrant in-process mutex).
 func (store *Store) appendEventLocked(sessionID string, input AppendEventInput) (Event, error) {
-	session, err := store.readMetadata(sessionID)
+	prepared, err := prepareAppendEventInputs([]AppendEventInput{input})
 	if err != nil {
 		return Event{}, err
 	}
-	payload, err := rawPayload(input.Payload)
+	events, err := store.appendPreparedEventsLocked(sessionID, prepared)
 	if err != nil {
 		return Event{}, err
 	}
+	return events[0], nil
+}
+
+// appendPreparedEventsLocked appends pre-validated events WITHOUT acquiring the
+// session lock. The caller MUST already hold store.lockSession(sessionID).
+func (store *Store) appendPreparedEventsLocked(sessionID string, inputs []preparedAppendEvent) ([]Event, error) {
+	if len(inputs) == 0 {
+		return []Event{}, nil
+	}
+	session, err := store.readMetadata(sessionID)
+	if err != nil {
+		return nil, err
+	}
 	sequence := session.EventCount + 1
 	// The events log is the source of truth for sequencing. metadata.EventCount is
 	// persisted separately (after the event line below), so a crash between the two
@@ -590,46 +624,54 @@ func (store *Store) appendEventLocked(sessionID string, input AppendEventInput)
 	if logSeq, err := store.lastEventSequence(sessionID); err == nil && logSeq >= sequence {
 		sequence = logSeq + 1
 	}
-	timestamp := store.timestamp()
-	event := Event{
-		ID:        fmt.Sprintf("%s:%d", sessionID, sequence),
-		SessionID: sessionID,
-		Sequence:  sequence,
-		Type:      input.Type,
-		CreatedAt: timestamp,
-		Payload:   payload,
-	}
-	data, err := json.Marshal(event)
-	if err != nil {
-		return Event{}, fmt.Errorf("encode zero session event: %w", err)
+	events := make([]Event, 0, len(inputs))
+	var batch bytes.Buffer
+	for index, input := range inputs {
+		timestamp := store.timestamp()
+		event := Event{
+			ID:        fmt.Sprintf("%s:%d", sessionID, sequence+index),
+			SessionID: sessionID,
+			Sequence:  sequence + index,
+			Type:      input.Type,
+			CreatedAt: timestamp,
+			Payload:   input.Payload,
+		}
+		data, err := json.Marshal(event)
+		if err != nil {
+			return nil, fmt.Errorf("encode zero session event: %w", err)
+		}
+		batch.Write(data)
+		batch.WriteByte('\n')
+		events = append(events, event)
 	}
 	file, err := os.OpenFile(store.eventsPath(sessionID), os.O_WRONLY|os.O_APPEND|os.O_CREATE, 0o600)
 	if err != nil {
-		return Event{}, fmt.Errorf("append zero session event: %w", err)
+		return nil, fmt.Errorf("append zero session event: %w", err)
 	}
-	if _, err := file.Write(append(data, '\n')); err != nil {
+	if _, err := file.Write(batch.Bytes()); err != nil {
 		_ = file.Close()
-		return Event{}, fmt.Errorf("append zero session event: %w", err)
+		return nil, fmt.Errorf("append zero session event: %w", err)
 	}
-	// fsync the event before reporting success: the derived metadata.json IS
+	// fsync the events before reporting success: the derived metadata.json IS
 	// fsync'd (writeMetadata), so without this a crash after the metadata flush
 	// but before the events.jsonl page reaches disk leaves EventCount ahead of the
-	// durable log — silently losing the just-appended event (incl. the checkpoint
+	// durable log — silently losing just-appended events (incl. checkpoints
 	// that /rewind targets). Make the log at least as durable as its metadata. (AUDIT-M12)
 	if err := file.Sync(); err != nil {
 		_ = file.Close()
-		return Event{}, fmt.Errorf("sync zero session event: %w", err)
+		return nil, fmt.Errorf("sync zero session event: %w", err)
 	}
 	if err := file.Close(); err != nil {
-		return Event{}, fmt.Errorf("close zero session event file: %w", err)
+		return nil, fmt.Errorf("close zero session event file: %w", err)
 	}
-	session.UpdatedAt = timestamp
-	session.EventCount = sequence
-	session.LastEventType = input.Type
+	last := events[len(events)-1]
+	session.UpdatedAt = last.CreatedAt
+	session.EventCount = last.Sequence
+	session.LastEventType = last.Type
 	if err := store.writeMetadata(session); err != nil {
-		return Event{}, err
+		return nil, err
 	}
-	return event, nil
+	return events, nil
 }
 
 // UpdateTitle replaces a session's Title and returns the updated metadata. It is
@@ -964,6 +1006,24 @@ func rawPayload(payload any) (json.RawMessage, error) {
 	return data, nil
 }
 
+func prepareAppendEventInputs(inputs []AppendEventInput) ([]preparedAppendEvent, error) {
+	prepared := make([]preparedAppendEvent, 0, len(inputs))
+	for _, input := range inputs {
+		if strings.TrimSpace(string(input.Type)) == "" {
+			return nil, fmt.Errorf("zero session event type is required")
+		}
+		payload, err := rawPayload(input.Payload)
+		if err != nil {
+			return nil, err
+		}
+		prepared = append(prepared, preparedAppendEvent{
+			Type:    input.Type,
+			Payload: payload,
+		})
+	}
+	return prepared, nil
+}
+
 func envValue(env map[string]string, key string) string {
 	if env != nil {
 		return env[key]

internal/tools/bash.go

@@ -83,7 +83,12 @@ func (tool bashTool) run(ctx context.Context, args map[string]any, engine *zeroS
 	if err != nil {
 		return errorResult("Error: Invalid arguments for bash: " + err.Error())
 	}
-	if issue := detectShellCommandIssue(commandText, runtime.GOOS); issue != nil {
+	// Resolve the command engine before the MSYS preflight check so an
+	// approved require_escalated call (commandEngine == nil, truly
+	// unsandboxed) can actually bypass the MSYS guard instead of being
+	// hard-blocked by the same check it was meant to escalate past.
+	commandEngine := commandEngineForSandboxPermissions(engine, sandboxPermissions)
+	if issue := detectShellCommandIssue(commandText, runtime.GOOS); issue != nil && !msysGuardBypassed(issue, commandEngine) {
 		return shellIssueBlockResult(*issue)
 	}
 
@@ -106,7 +111,6 @@ func (tool bashTool) run(ctx context.Context, args map[string]any, engine *zeroS
 		"cwd":        relativeCwd,
 		"timeout_ms": strconv.Itoa(timeoutMS),
 	}
-	commandEngine := commandEngineForSandboxPermissions(engine, sandboxPermissions)
 	if commandEngine == nil && sandboxPermissions == SandboxPermissionsRequireEscalated {
 		meta["sandbox_permissions"] = string(SandboxPermissionsRequireEscalated)
 	}
@@ -126,8 +130,8 @@ func (tool bashTool) run(ctx context.Context, args map[string]any, engine *zeroS
 	// can't grow Zero's memory before truncation: only the head+tail each stream
 	// will ever surface to the model are retained, the middle is discarded as it
 	// streams, and the true size is counted for the truncation marker.
-	stdout := newBoundedBuffer(bashOutputBudgetBytes, bashOutputBudgetBytes)
-	stderr := newBoundedBuffer(bashOutputBudgetBytes, bashOutputBudgetBytes)
+	stdout := newBoundedBuffer(bashCaptureBudgetBytes, bashCaptureBudgetBytes)
+	stderr := newBoundedBuffer(bashCaptureBudgetBytes, bashCaptureBudgetBytes)
 	command.Stdout = stdout
 	command.Stderr = stderr
 
@@ -167,7 +171,7 @@ func (tool bashTool) run(ctx context.Context, args map[string]any, engine *zeroS
 		outText, errText, truncated := budgetBashCapture(stdoutText, stdout.total, stderrText, stderrTotal, meta)
 		return Result{
 			Status:    StatusError,
-			Output:    formatBashOutputWithShellHint(commandText, outText, errText, exitCode, meta),
+			Output:    formatBashOutputWithShellHint(outText, errText, exitCode, meta),
 			Truncated: truncated,
 			Meta:      meta,
 		}
@@ -178,7 +182,7 @@ func (tool bashTool) run(ctx context.Context, args map[string]any, engine *zeroS
 	if meta[SandboxLikelyDeniedMeta] == "true" {
 		return Result{
 			Status:    StatusError,
-			Output:    formatBashOutputWithShellHint(commandText, outText, errText, exitCode, meta),
+			Output:    formatBashOutputWithShellHint(outText, errText, exitCode, meta),
 			Truncated: truncated,
 			Meta:      meta,
 		}
@@ -198,6 +202,18 @@ func commandEngineForSandboxPermissions(engine *zeroSandbox.Engine, sandboxPermi
 	return engine
 }
 
+// msysGuardBypassed reports whether a windows_msys_sandbox preflight issue no
+// longer applies because sandbox_permissions: require_escalated actually
+// resolved to unsandboxed, host-level execution (commandEngine is nil only
+// then, per commandEngineForSandboxPermissions). MSYS coreutils fail because
+// of the sandbox's restricted token/handles, so running outside it removes
+// the failure mode this guard exists for. Any other issue kind (e.g. a real
+// cmd.exe syntax problem) still blocks regardless of escalation, since
+// running outside the sandbox does not fix a syntax error.
+func msysGuardBypassed(issue *shellIssue, commandEngine *zeroSandbox.Engine) bool {
+	return issue.Kind == windowsMsysSandboxKind && commandEngine == nil
+}
+
 // appendSandboxBlocks appends a <sandbox_blocks> block listing the denials
 // the sandbox log monitor captured, so the model can see what was blocked. With no
 // blocks the stderr is returned unchanged.
@@ -370,12 +386,21 @@ func formatBashOutput(stdout string, stderr string, exitCode int) string {
 	return strings.Join(parts, "\n")
 }
 
-// bashOutputBudgetBytes caps each of stdout/stderr shown to the model. bash is the
-// one tool that can emit unbounded output (`cat large.log`, `find /`, verbose test
-// runs); every other read/search tool already budgets its output. Head+tail
-// truncation keeps both the start and the end of an oversized stream, since
-// build/test failures usually surface at the tail.
-const bashOutputBudgetBytes = 96 * 1024
+// bashOutputBudgetBytes caps each of stdout/stderr shown to the model (32 KiB
+// ≈ 8k tokens per stream). bash is the one tool that can emit unbounded output
+// (`cat large.log`, `find /`, verbose test runs); a chatty build log at the old
+// 96 KiB budget injected ~24k tokens per call and was then re-billed on every
+// following turn. Head+tail truncation keeps both the start and the end of an
+// oversized stream, since build/test failures usually surface at the tail, and
+// the full captured text is spilled to disk so nothing is lost — the model
+// greps/reads the spill instead of re-running the command.
+const bashOutputBudgetBytes = 32 * 1024
+
+// bashCaptureBudgetBytes bounds the head and tail retained IN MEMORY per
+// stream during capture. Deliberately larger than the emit budget: the extra
+// retained bytes never reach the transcript, but they make the spill file —
+// the model's recovery path — cover 6× more of the output.
+const bashCaptureBudgetBytes = 96 * 1024
 
 // budgetBashOutput truncates stdout and stderr to bashOutputBudgetBytes each,
 // keeping the head and tail of anything larger, and records raw/emitted byte
@@ -395,6 +420,19 @@ func budgetBashCapture(out string, outTotal int, errStr string, errTotal int, me
 	outText, outRaw, outTrunc := truncateHeadTailWithTotal(out, outTotal, bashOutputBudgetBytes)
 	errText, errRaw, errTrunc := truncateHeadTailWithTotal(errStr, errTotal, bashOutputBudgetBytes)
 	truncated := outTrunc || errTrunc
+	if truncated {
+		if spillPath := spillBashStreams(out, outTotal, errStr, errTotal); spillPath != "" {
+			hint := "\n[zero] captured output saved to " + spillPath + " (grep or read_file it instead of re-running)"
+			if errTrunc {
+				errText += hint
+			} else {
+				outText += hint
+			}
+			if meta != nil {
+				meta["spill_path"] = spillPath
+			}
+		}
+	}
 	if meta != nil {
 		emitted := len(outText) + len(errText)
 		meta["raw_bytes"] = strconv.Itoa(outRaw + errRaw)
@@ -407,6 +445,43 @@ func budgetBashCapture(out string, outTotal int, errStr string, errTotal int, me
 	return outText, errText, truncated
 }
 
+// spillBashStreams writes the retained (capture-bounded) stdout and stderr to
+// the spill directory as one sectioned file and returns its path, or "" when
+// spilling fails. The spill holds up to bashCaptureBudgetBytes of head and
+// tail per stream — everything zero kept in memory, which is more than the
+// emit budget shows the model but not necessarily the whole output. When the
+// capture itself dropped the middle of a stream (total exceeds the retained
+// bytes), a gap marker is inserted at the head/tail junction so the spilled
+// log never reads as contiguous when it is not.
+func spillBashStreams(stdout string, stdoutTotal int, stderr string, stderrTotal int) string {
+	stdout = sectionWithCaptureGap(stdout, stdoutTotal)
+	stderr = sectionWithCaptureGap(stderr, stderrTotal)
+	var combined strings.Builder
+	combined.Grow(len(stdout) + len(stderr) + 64)
+	combined.WriteString("### stdout\n")
+	combined.WriteString(stdout)
+	if !strings.HasSuffix(stdout, "\n") {
+		combined.WriteString("\n")
+	}
+	combined.WriteString("### stderr\n")
+	combined.WriteString(stderr)
+	return spillTruncatedOutput("bash", combined.String())
+}
+
+// sectionWithCaptureGap marks the point where boundedBuffer dropped the middle
+// of a stream. When total exceeds the retained bytes, the retained text is the
+// frozen head (bashCaptureBudgetBytes, always full once overflow happened)
+// followed immediately by the rolling tail — the junction sits at the head cap,
+// snapped back to a rune boundary.
+func sectionWithCaptureGap(text string, total int) string {
+	if total <= len(text) || len(text) <= bashCaptureBudgetBytes {
+		return text
+	}
+	head := utf8Prefix(text, bashCaptureBudgetBytes)
+	marker := fmt.Sprintf("\n[zero] capture gap: %d bytes omitted from the middle of this stream\n", total-len(text))
+	return head + marker + text[len(head):]
+}
+
 // boundedBuffer is an io.Writer that retains at most headCap bytes from the start
 // and tailCap bytes from the end of a stream while counting the total written, so
 // a command emitting unbounded output (`cat huge.log`, `yes`) cannot grow Zero's
@@ -461,14 +536,6 @@ func (b *boundedBuffer) retained() string {
 	return string(b.head) + string(b.tail)
 }
 
-// truncateHeadTail keeps the first and last halves of value when it exceeds
-// maxBytes, dropping the middle behind a marker. Returns the possibly-truncated
-// text, the raw byte length, and whether truncation happened.
-func truncateHeadTail(value string, maxBytes int) (string, int, bool) {
-	// value holds the whole stream, so its length is the true raw size.
-	return truncateHeadTailWithTotal(value, len(value), maxBytes)
-}
-
 // truncateHeadTailWithTotal head+tail-truncates value to maxBytes, using total —
 // the full original byte count — for the "N bytes omitted" marker and the raw
 // count. total may exceed len(value) when the middle was already discarded during
@@ -488,9 +555,9 @@ func truncateHeadTailWithTotal(value string, total, maxBytes int) (string, int,
 	return utf8Prefix(value, head) + marker + utf8Suffix(value, tail), total, true
 }
 
-func formatBashOutputWithShellHint(command string, stdout string, stderr string, exitCode int, meta map[string]string) string {
+func formatBashOutputWithShellHint(stdout string, stderr string, exitCode int, meta map[string]string) string {
 	output := formatBashOutput(stdout, stderr, exitCode)
-	if issue := detectShellOutputIssue(command, stdout+"\n"+stderr, runtime.GOOS); issue != nil {
+	if issue := detectShellOutputIssue(stdout+"\n"+stderr, runtime.GOOS); issue != nil {
 		meta["shell_issue"] = issue.Kind
 		output = appendShellIssueHint(output, *issue)
 	}

internal/tools/bash_budget_test.go

@@ -2,11 +2,23 @@ package tools
 
 import (
 	"fmt"
+	"os"
 	"strconv"
 	"strings"
 	"testing"
 )
 
+// setTestTempDir points every platform's temp-dir lookup at a per-test
+// directory so spill files never land in the real temp dir: os.TempDir reads
+// TMPDIR on Unix but TMP/TEMP on Windows.
+func setTestTempDir(t *testing.T) {
+	t.Helper()
+	dir := t.TempDir()
+	t.Setenv("TMPDIR", dir)
+	t.Setenv("TMP", dir)
+	t.Setenv("TEMP", dir)
+}
+
 // Small output passes through untouched and records raw==emitted, no truncated flag.
 func TestBudgetBashOutputSmallPassesThrough(t *testing.T) {
 	meta := map[string]string{}
@@ -26,8 +38,10 @@ func TestBudgetBashOutputSmallPassesThrough(t *testing.T) {
 }
 
 // Oversized stdout is truncated head+tail: both the first and last lines survive,
-// the middle is dropped behind a marker, and meta is flagged.
+// the middle is dropped behind a marker, meta is flagged, and the captured text
+// is spilled to a re-readable file.
 func TestBudgetBashOutputTruncatesHeadAndTail(t *testing.T) {
+	setTestTempDir(t)
 	head := "FIRST_LINE_MARKER\n"
 	tail := "\nLAST_LINE_MARKER"
 	big := head + strings.Repeat("x", bashOutputBudgetBytes) + tail
@@ -47,9 +61,23 @@ func TestBudgetBashOutputTruncatesHeadAndTail(t *testing.T) {
 	if !strings.Contains(out, "output truncated") {
 		t.Fatalf("expected a truncation marker, got:\n%s", out[:200])
 	}
-	if len(out) > bashOutputBudgetBytes {
+	// The spill hint (path length varies) is the only allowed overage past the budget.
+	if len(out) > bashOutputBudgetBytes+512 {
 		t.Fatalf("emitted %d bytes exceeds budget %d", len(out), bashOutputBudgetBytes)
 	}
+	if !strings.Contains(out, "captured output saved to ") {
+		t.Fatalf("truncated bash output must carry a spill hint:\n%s", out[len(out)-300:])
+	}
+	if meta["spill_path"] == "" {
+		t.Fatal("spill path missing from meta")
+	}
+	content, err := os.ReadFile(meta["spill_path"])
+	if err != nil {
+		t.Fatalf("spill file unreadable: %v", err)
+	}
+	if !strings.Contains(string(content), "### stdout") || !strings.Contains(string(content), strings.Repeat("x", 1024)) {
+		t.Fatalf("spill must hold the sectioned captured streams (got %d bytes)", len(content))
+	}
 	if meta["truncated"] != "true" {
 		t.Fatalf("expected truncated=true, got %v", meta)
 	}
@@ -100,10 +128,12 @@ func TestBoundedBufferKeepsHeadAndTailBounded(t *testing.T) {
 // budgetBashCapture reports the TRUE total (not the retained size) in the marker
 // and raw_bytes, even though only a bounded head+tail was ever held in memory.
 func TestBudgetBashCaptureReportsTrueTotal(t *testing.T) {
-	// Retained head+tail as boundedBuffer would hand over; the real command produced
-	// far more than was kept.
-	retained := "HEAD_START" + strings.Repeat("y", bashOutputBudgetBytes) + "TAIL_END"
-	total := 10 * bashOutputBudgetBytes
+	setTestTempDir(t)
+	// Retained head+tail as boundedBuffer would hand over after overflow: the
+	// frozen head is full at bashCaptureBudgetBytes, then the rolling tail; the
+	// real command produced far more than was kept.
+	retained := "HEAD_START" + strings.Repeat("y", bashCaptureBudgetBytes) + "TAIL_END"
+	total := 10 * bashCaptureBudgetBytes
 
 	meta := map[string]string{}
 	out, _, truncated := budgetBashCapture(retained, total, "", 0, meta)
@@ -114,7 +144,8 @@ func TestBudgetBashCaptureReportsTrueTotal(t *testing.T) {
 	if !strings.Contains(out, "HEAD_START") || !strings.Contains(out, "TAIL_END") {
 		t.Fatalf("head/tail lost after budgeting:\n%s", out[:min(120, len(out))])
 	}
-	if len(out) > bashOutputBudgetBytes {
+	// Spill hint is the only allowed overage past the budget.
+	if len(out) > bashOutputBudgetBytes+512 {
 		t.Fatalf("emitted %d bytes exceeds budget %d", len(out), bashOutputBudgetBytes)
 	}
 	if meta["raw_bytes"] != strconv.Itoa(total) {
@@ -124,4 +155,29 @@ func TestBudgetBashCaptureReportsTrueTotal(t *testing.T) {
 	if !strings.Contains(out, strconv.Itoa(total-bashOutputBudgetBytes)) {
 		t.Fatalf("marker should cite the true omitted byte count:\n%s", out[:min(200, len(out))])
 	}
+
+	// The spill must be recorded, sectioned, and carry a capture-gap marker at
+	// the head/tail junction — the capture dropped the middle, so the spilled
+	// log must never read as contiguous.
+	if meta["spill_path"] == "" {
+		t.Fatal("spill path missing from meta")
+	}
+	content, err := os.ReadFile(meta["spill_path"])
+	if err != nil {
+		t.Fatalf("spill file unreadable: %v", err)
+	}
+	if !strings.Contains(string(content), "### stdout") {
+		t.Fatal("spill must be sectioned by stream")
+	}
+	gapMarker := fmt.Sprintf("capture gap: %d bytes omitted", total-len(retained))
+	gapIndex := strings.Index(string(content), gapMarker)
+	if gapIndex < 0 {
+		t.Fatalf("spill missing capture-gap marker %q", gapMarker)
+	}
+	// The junction sits right after the frozen head (plus the section header),
+	// not appended at the end of the stream.
+	headerOffset := len("### stdout\n")
+	if gapIndex < headerOffset+bashCaptureBudgetBytes-64 || gapIndex > headerOffset+bashCaptureBudgetBytes+64 {
+		t.Fatalf("capture-gap marker at offset %d, want ~%d (the head cap)", gapIndex, headerOffset+bashCaptureBudgetBytes)
+	}
 }

internal/tools/bash_tool_test.go

@@ -181,9 +181,13 @@ func TestDetectShellCommandIssueFlagsPipedPosixUtilities(t *testing.T) {
 		`cat file.txt | wc -l`,
 		`some_command | tail -n 20`,
 	} {
-		if issue := detectShellCommandIssue(command, "windows"); issue == nil {
+		issue := detectShellCommandIssue(command, "windows")
+		if issue == nil {
 			t.Fatalf("expected POSIX utility pipeline to be flagged for %q", command)
 		}
+		if issue.Kind != "windows_msys_sandbox" {
+			t.Fatalf("expected windows_msys_sandbox for %q, got %q", command, issue.Kind)
+		}
 	}
 }
 
@@ -195,7 +199,7 @@ func TestDetectShellCommandIssueAllowsUnrelatedCommands(t *testing.T) {
 		`echo header text`,
 		`tail-log.sh`,
 		`grep-cli --version`,
-		`sed.exe --help`,
+		`mytool.exe --help`,
 	} {
 		if issue := detectShellCommandIssue(command, "windows"); issue != nil {
 			t.Fatalf("expected unrelated command to pass for %q, got %#v", command, issue)
@@ -204,7 +208,7 @@ func TestDetectShellCommandIssueAllowsUnrelatedCommands(t *testing.T) {
 }
 
 func TestDetectShellOutputIssueAddsWindowsSyntaxHint(t *testing.T) {
-	issue := detectShellOutputIssue(`cd /d/tmp/zero-pr-158 && ls -la`, "The syntax of the command is incorrect.", "windows")
+	issue := detectShellOutputIssue("The syntax of the command is incorrect.", "windows")
 	if issue == nil {
 		t.Fatal("expected Windows syntax error to get shell guidance")
 	}
@@ -434,6 +438,105 @@ func TestRegistryRunsWithDegradedUnavailableNativeSandbox(t *testing.T) {
 	}
 }
 
+// TestBashToolRequireEscalatedMsysGuard covers the boundary of the fix for an
+// escalation-vs-preflight ordering bug: the MSYS sandbox guard exists only
+// because MSYS/Cygwin coreutils fail under the write-restricted sandbox, so
+// once sandbox_permissions: require_escalated is actually approved (running
+// the command unsandboxed), the guard must get out of the way, but an
+// unrelated windows_shell_syntax issue (a real cmd.exe syntax problem, not a
+// sandbox interaction) must still block regardless of escalation.
+func TestBashToolRequireEscalatedMsysGuard(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		t.Skip("windows-only MSYS sandbox guard")
+	}
+	root := t.TempDir()
+	newEngine := func() *sandbox.Engine {
+		return sandbox.NewEngine(sandbox.EngineOptions{
+			WorkspaceRoot: root,
+			Policy:        sandbox.DefaultPolicy(),
+			Backend:       sandbox.Backend{Name: sandbox.BackendUnavailable, Message: "native sandbox unavailable"},
+		})
+	}
+	registry := NewRegistry()
+	registry.Register(NewBashTool(root))
+
+	t.Run("default sandboxing still blocks an MSYS-prone command", func(t *testing.T) {
+		result := registry.RunWithOptions(context.Background(), "bash", map[string]any{
+			"command": "cat somefile.txt",
+		}, RunOptions{
+			PermissionGranted: true,
+			Sandbox:           newEngine(),
+			PermissionMode:    string(sandbox.PermissionModeAsk),
+		})
+		if result.Meta["shell_issue"] != "windows_msys_sandbox" {
+			t.Fatalf("expected windows_msys_sandbox block without escalation, got %#v", result)
+		}
+	})
+
+	t.Run("approved require_escalated bypasses the MSYS guard", func(t *testing.T) {
+		result := registry.RunWithOptions(context.Background(), "bash", map[string]any{
+			"command":             "cat somefile.txt",
+			"sandbox_permissions": string(SandboxPermissionsRequireEscalated),
+		}, RunOptions{
+			PermissionGranted: true,
+			Sandbox:           newEngine(),
+			PermissionMode:    string(sandbox.PermissionModeAsk),
+		})
+		// Assert on the preflight block sentinel (exit_code "-1", set only by
+		// shellIssueBlockResult) rather than shell_issue: once the guard is
+		// bypassed, "cat somefile.txt" actually runs, and its real,
+		// PATH-dependent output could otherwise trip the unrelated
+		// post-execution detectShellOutputIssue heuristic and make this
+		// assertion flaky for reasons unrelated to the guard under test.
+		if result.Meta["exit_code"] == "-1" {
+			t.Fatalf("expected approved require_escalated to bypass the MSYS guard, got blocked: %#v", result)
+		}
+	})
+
+	t.Run("approved require_escalated still blocks an unrelated syntax issue", func(t *testing.T) {
+		result := registry.RunWithOptions(context.Background(), "bash", map[string]any{
+			"command":             `cd /d/tmp/zero-pr-158 && dir`,
+			"sandbox_permissions": string(SandboxPermissionsRequireEscalated),
+		}, RunOptions{
+			PermissionGranted: true,
+			Sandbox:           newEngine(),
+			PermissionMode:    string(sandbox.PermissionModeAsk),
+		})
+		if result.Meta["shell_issue"] != "windows_shell_syntax" {
+			t.Fatalf("expected windows_shell_syntax block to still apply under require_escalated, got %#v", result)
+		}
+	})
+}
+
+// TestBashToolIgnoresMsysMarkersInCommandArgumentsAfterFailure guards the
+// post-execution MSYS heuristic against treating the command line itself as
+// evidence. The helper command below fails for a reason unrelated to MSYS
+// (a plain non-zero exit), but its own argument text quotes an MSYS crash
+// marker the way a PR-comment or commit-message argument might. Before the
+// fix, detectShellOutputIssue scanned command+output together and would have
+// misdiagnosed this as an MSYS sandbox failure even though the real
+// stdout/stderr never mentions MSYS at all.
+func TestBashToolIgnoresMsysMarkersInCommandArgumentsAfterFailure(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		t.Skip("windows-only MSYS output guard")
+	}
+	root := t.TempDir()
+	// The helper only reads argv[2] ("fail"); this trailing quoted argument is
+	// otherwise unused by the helper but still part of the command line text.
+	command := helperCommand("fail") + ` "fatal error - CreateFileMapping S-1-5-21, Win32 error 5. Terminating. cygheap_user::init"`
+
+	result := NewBashTool(root).Run(context.Background(), map[string]any{
+		"command": command,
+	})
+
+	if result.Status != StatusError || result.Meta["exit_code"] != "7" {
+		t.Fatalf("expected the helper's real exit 7 failure, got %s: %#v", result.Status, result)
+	}
+	if result.Meta["shell_issue"] == "windows_msys_sandbox" {
+		t.Fatalf("expected the MSYS marker in the command's own argument text to be ignored, got %#v", result)
+	}
+}
+
 func TestBashToolRunsWithDegradedUnavailableNativeSandbox(t *testing.T) {
 	root := t.TempDir()
 	policy := sandbox.DefaultPolicy()

internal/tools/edit_replacers.go

@@ -58,7 +58,7 @@ func fuzzyEditMatch(content, find string, replaceAll bool) (string, error) {
 				continue
 			}
 			seen[search] = true
-			if strings.Index(content, search) < 0 {
+			if !strings.Contains(content, search) {
 				continue
 			}
 			candidates = append(candidates, search)

internal/tools/exec_command.go

@@ -517,7 +517,12 @@ func (tool execCommandTool) run(ctx context.Context, args map[string]any, engine
 	if err != nil {
 		return errorResult("Error: Invalid arguments for exec_command: " + err.Error())
 	}
-	if issue := detectShellCommandIssue(commandText, runtimeGOOS()); issue != nil {
+	// Resolve the command engine before the MSYS preflight check so an
+	// approved require_escalated call (commandEngine == nil, truly
+	// unsandboxed) can actually bypass the MSYS guard instead of being
+	// hard-blocked by the same check it was meant to escalate past.
+	commandEngine := commandEngineForSandboxPermissions(engine, sandboxPermissions)
+	if issue := detectShellCommandIssue(commandText, runtimeGOOS()); issue != nil && !msysGuardBypassed(issue, commandEngine) {
 		return shellIssueBlockResult(*issue)
 	}
 	if interactive := zeroSandbox.DetectInteractiveCommand(commandText, runtimeGOOS()); interactive.Interactive {
@@ -860,6 +865,12 @@ func execToolResult(input execToolResultInput) Result {
 		status = StatusError
 	}
 	body := formatExecCommandOutput(output, input.sessionID, input.exited, input.exitCode, input.interrupted)
+	if status == StatusError && input.exited && !input.interrupted {
+		if issue := detectShellOutputIssue(output, runtimeGOOS()); issue != nil {
+			meta["shell_issue"] = issue.Kind
+			body = appendShellIssueHint(body, *issue)
+		}
+	}
 	if input.outputBufferTruncated {
 		// Appended after truncateExecOutput's own head/tail slicing, not
 		// embedded in the text that goes through it — a marker inside that

internal/tools/exec_command_test.go

@@ -141,6 +141,46 @@ func TestExecCommandRequireEscalatedBypassesNativeSandboxAfterApproval(t *testin
 	}
 }
 
+// TestExecCommandRequireEscalatedBypassesMsysGuardAfterApproval mirrors
+// TestBashToolRequireEscalatedMsysGuard for exec_command: the MSYS sandbox
+// guard exists only because MSYS/Cygwin coreutils fail under the
+// write-restricted sandbox, so once require_escalated is actually approved
+// (unsandboxed execution), the guard must not block the same command it was
+// meant to let escalate past.
+func TestExecCommandRequireEscalatedBypassesMsysGuardAfterApproval(t *testing.T) {
+	if runtime.GOOS != "windows" {
+		t.Skip("windows-only MSYS sandbox guard")
+	}
+	root := t.TempDir()
+	manager := newExecSessionManager()
+	registry := NewRegistry()
+	registry.Register(NewScopedExecCommandTool(root, nil, manager))
+	engine := sandbox.NewEngine(sandbox.EngineOptions{
+		WorkspaceRoot: root,
+		Policy:        sandbox.DefaultPolicy(),
+		Backend:       sandbox.Backend{Name: sandbox.BackendUnavailable, Message: "native sandbox unavailable"},
+	})
+
+	result := registry.RunWithOptions(context.Background(), ExecCommandToolName, map[string]any{
+		"cmd":                 "cat somefile.txt",
+		"sandbox_permissions": string(SandboxPermissionsRequireEscalated),
+	}, RunOptions{
+		PermissionGranted: true,
+		Sandbox:           engine,
+		PermissionMode:    string(sandbox.PermissionModeAsk),
+	})
+
+	// Assert on the preflight block sentinel (exit_code "-1", set only by
+	// shellIssueBlockResult) rather than shell_issue: once the guard is
+	// bypassed, "cat somefile.txt" actually runs, and its real,
+	// PATH-dependent output could otherwise trip the unrelated
+	// post-execution detectShellOutputIssue heuristic and make this
+	// assertion flaky for reasons unrelated to the guard under test.
+	if result.Meta["exit_code"] == "-1" {
+		t.Fatalf("expected approved require_escalated to bypass the MSYS guard, got blocked: %#v", result)
+	}
+}
+
 func TestExecCommandReturnsExitCodeWhenCommandCompletesDuringInitialYield(t *testing.T) {
 	root := t.TempDir()
 	manager := newExecSessionManager()

internal/tools/output_ceiling.go

@@ -0,0 +1,81 @@
+package tools
+
+import (
+	"os"
+	"strconv"
+	"strings"
+)
+
+// Universal output ceiling. Every tool result leaving the registry boundary is
+// capped at a single token-denominated budget unless the tool manages its own
+// deliberate budget (selfBudgeting below). This is the safety net for tools
+// with no cap of their own — web_fetch bodies, skill files, MCP server tools,
+// browser snapshots, anything added later — so no single call can flood the
+// context window with output that is then re-billed on every following turn.
+// Truncation keeps head+tail and spills the full text to disk (re-readable via
+// grep/read_file), so nothing is lost, only deferred.
+
+// defaultOutputCeilingTokens is the per-call ceiling in estimated tokens
+// (bytes/4). 16k tokens = 64 KiB — deliberately equal to the search-tool
+// budget: generous enough for a large fetched document, small enough that one
+// call cannot eat a third of a small context window.
+const defaultOutputCeilingTokens = 16_000
+
+// outputCeilingEnv overrides the ceiling (in tokens). Zero or negative
+// disables the ceiling entirely; unset or unparsable keeps the default.
+const outputCeilingEnv = "ZERO_TOOL_OUTPUT_CEILING_TOKENS"
+
+// selfBudgeting marks a tool that enforces its own deliberate output budget —
+// possibly model-raisable (exec_command) — which the registry ceiling must not
+// second-guess. The method is unexported on purpose: only tools in this
+// package can opt out, so an MCP-served tool can never exempt itself.
+type selfBudgeting interface{ managesOutputBudget() }
+
+// The exemption list, kept in one place. Each of these applies its own budget
+// before returning: bash (bashOutputBudgetBytes per stream + spill),
+// exec_command (model-raisable token budget + spill), read tools (128 KiB),
+// search tools (64 KiB).
+func (bashTool) managesOutputBudget()             {}
+func (execCommandTool) managesOutputBudget()      {}
+func (readFileTool) managesOutputBudget()         {}
+func (readMinifiedFileTool) managesOutputBudget() {}
+func (grepTool) managesOutputBudget()             {}
+func (globTool) managesOutputBudget()             {}
+func (listDirectoryTool) managesOutputBudget()    {}
+
+func resolveOutputCeilingTokens() int {
+	raw := strings.TrimSpace(os.Getenv(outputCeilingEnv))
+	if raw == "" {
+		return defaultOutputCeilingTokens
+	}
+	parsed, err := strconv.Atoi(raw)
+	if err != nil {
+		return defaultOutputCeilingTokens
+	}
+	return parsed
+}
+
+// enforceOutputCeiling truncates an over-ceiling result to head+tail within
+// the token budget, spilling the full (already redaction-scrubbed) output to
+// disk with a recovery hint. Runs after scrubResultSecrets so the transcript
+// and the spill file agree on what was hidden.
+func enforceOutputCeiling(toolName string, result Result) Result {
+	ceiling := resolveOutputCeilingTokens()
+	if ceiling <= 0 {
+		return result
+	}
+	if len(result.Output) <= ceiling*4 {
+		return result
+	}
+	rawBytes := len(result.Output)
+	truncated, _ := truncateExecOutputSpill(result.Output, ceiling, toolName)
+	result.Output = truncated
+	result.Truncated = true
+	if result.Meta == nil {
+		result.Meta = map[string]string{}
+	}
+	result.Meta["raw_bytes"] = strconv.Itoa(rawBytes)
+	result.Meta["emitted_bytes"] = strconv.Itoa(len(result.Output))
+	result.Meta["estimated_tokens"] = strconv.Itoa(estimatedTokensFromBytes(len(result.Output)))
+	return result
+}

internal/tools/output_ceiling_test.go

@@ -0,0 +1,140 @@
+package tools
+
+import (
+	"context"
+	"os"
+	"strconv"
+	"strings"
+	"testing"
+)
+
+// ceilingFakeTool is a minimal tool with no output budget of its own — the
+// stand-in for an MCP-served tool or any future builtin that forgets to cap
+// its output.
+type ceilingFakeTool struct {
+	baseTool
+	output string
+}
+
+func (tool ceilingFakeTool) Run(context.Context, map[string]any) Result {
+	return okResult(tool.output)
+}
+
+// ceilingExemptTool is the same fake but marked self-budgeting.
+type ceilingExemptTool struct{ ceilingFakeTool }
+
+func (ceilingExemptTool) managesOutputBudget() {}
+
+func newCeilingFakeTool(name, output string) ceilingFakeTool {
+	return ceilingFakeTool{
+		baseTool: baseTool{name: name, safety: readOnlySafety("test tool")},
+		output:   output,
+	}
+}
+
+// An unbudgeted tool's oversized output is capped at the universal ceiling,
+// head and tail survive, and the full output is spilled to a re-readable file.
+func TestOutputCeilingCapsUnbudgetedTool(t *testing.T) {
+	setTestTempDir(t)
+	big := "HEAD_MARK\n" + strings.Repeat("z", defaultOutputCeilingTokens*4*3) + "\nTAIL_MARK"
+
+	registry := NewRegistry()
+	registry.Register(newCeilingFakeTool("fake_big", big))
+	result := registry.Run(context.Background(), "fake_big", map[string]any{})
+
+	if !result.Truncated {
+		t.Fatal("over-ceiling output must report truncated=true")
+	}
+	maxBytes := defaultOutputCeilingTokens * 4
+	if len(result.Output) > maxBytes+512 {
+		t.Fatalf("emitted %d bytes, ceiling is %d", len(result.Output), maxBytes)
+	}
+	if !strings.Contains(result.Output, "HEAD_MARK") || !strings.Contains(result.Output, "TAIL_MARK") {
+		t.Fatal("head/tail lost at the ceiling")
+	}
+	if result.Meta["raw_bytes"] != strconv.Itoa(len(big)) {
+		t.Fatalf("raw_bytes = %s, want %d", result.Meta["raw_bytes"], len(big))
+	}
+	if !strings.Contains(result.Output, "full output saved to ") {
+		t.Fatalf("ceiling truncation must include a spill hint: %q", result.Output[:200])
+	}
+	start := strings.Index(result.Output, "full output saved to ") + len("full output saved to ")
+	end := strings.Index(result.Output[start:], " (grep")
+	content, err := os.ReadFile(result.Output[start : start+end])
+	if err != nil {
+		t.Fatalf("spill file unreadable: %v", err)
+	}
+	if string(content) != big {
+		t.Fatalf("spill must hold the full output: got %d bytes, want %d", len(content), len(big))
+	}
+}
+
+// A self-budgeting tool's output passes the boundary untouched even when it
+// exceeds the universal ceiling — its own (possibly model-raised) budget wins.
+func TestOutputCeilingSkipsSelfBudgetingTool(t *testing.T) {
+	big := strings.Repeat("z", defaultOutputCeilingTokens*4*2)
+	registry := NewRegistry()
+	registry.Register(ceilingExemptTool{newCeilingFakeTool("fake_exempt", big)})
+
+	result := registry.Run(context.Background(), "fake_exempt", map[string]any{})
+	if result.Truncated || result.Output != big {
+		t.Fatalf("self-budgeting tool must bypass the ceiling (truncated=%v, %d bytes)", result.Truncated, len(result.Output))
+	}
+}
+
+// Under-ceiling output is untouched and gains no budget metadata.
+func TestOutputCeilingSmallOutputUntouched(t *testing.T) {
+	registry := NewRegistry()
+	registry.Register(newCeilingFakeTool("fake_small", "hello"))
+
+	result := registry.Run(context.Background(), "fake_small", map[string]any{})
+	if result.Truncated || result.Output != "hello" {
+		t.Fatalf("small output altered: %+v", result)
+	}
+	if _, ok := result.Meta["raw_bytes"]; ok {
+		t.Fatal("small output must not gain budget metadata")
+	}
+}
+
+// ZERO_TOOL_OUTPUT_CEILING_TOKENS tightens, loosens, or disables the ceiling.
+func TestOutputCeilingEnvOverride(t *testing.T) {
+	setTestTempDir(t)
+	big := strings.Repeat("z", 100*1024)
+
+	t.Setenv(outputCeilingEnv, "1000")
+	registry := NewRegistry()
+	registry.Register(newCeilingFakeTool("fake_env", big))
+	result := registry.Run(context.Background(), "fake_env", map[string]any{})
+	if !result.Truncated || len(result.Output) > 1000*4+512 {
+		t.Fatalf("ceiling override ignored: truncated=%v, %d bytes", result.Truncated, len(result.Output))
+	}
+
+	t.Setenv(outputCeilingEnv, "0")
+	result = registry.Run(context.Background(), "fake_env", map[string]any{})
+	if result.Truncated || len(result.Output) != len(big) {
+		t.Fatalf("ceiling=0 must disable the net: truncated=%v, %d bytes", result.Truncated, len(result.Output))
+	}
+}
+
+// The exemption list matches the tools that really do budget themselves, and
+// the unbudgeted ones (web_fetch, skill, browser) stay under the net.
+func TestSelfBudgetingExemptionList(t *testing.T) {
+	dir := t.TempDir()
+	exempt := []Tool{
+		NewBashTool(dir),
+		NewExecCommandTool(dir, newExecSessionManager()),
+		NewReadFileTool(dir),
+		NewReadMinifiedFileTool(dir),
+		NewGrepTool(dir),
+		NewGlobTool(dir),
+		NewListDirectoryTool(dir),
+	}
+	for _, tool := range exempt {
+		if _, ok := tool.(selfBudgeting); !ok {
+			t.Errorf("%s must be exempt from the output ceiling", tool.Name())
+		}
+	}
+	if _, ok := NewWebFetchTool().(selfBudgeting); ok {
+		t.Error("web_fetch must NOT be exempt — the ceiling is its only budget")
+	}
+}

internal/tools/registry.go

@@ -123,13 +123,24 @@ func (registry *Registry) Run(ctx context.Context, name string, args map[string]
 func (registry *Registry) RunWithOptions(ctx context.Context, name string, args map[string]any, options RunOptions) (result Result) {
 	// Every return path passes through scrubResultSecrets exactly once, so denial,
 	// permission, and unknown-tool error messages (which can echo secret-bearing
-	// args/paths) are redacted at the boundary just like tool output.
-	defer func() { result = scrubResultSecrets(result) }()
+	// args/paths) are redacted at the boundary just like tool output. The output
+	// ceiling runs after the scrub so the transcript and the spill file agree on
+	// what was hidden.
+	ceilingExempt := false
+	defer func() {
+		result = scrubResultSecrets(result)
+		if !ceilingExempt {
+			result = enforceOutputCeiling(name, result)
+		}
+	}()
 
 	tool, ok := registry.Get(name)
 	if !ok {
 		return errorResult(`Error: Unknown tool "` + name + `".`)
 	}
+	if _, ok := tool.(selfBudgeting); ok {
+		ceilingExempt = true
+	}
 	if rejecter, ok := tool.(PrePermissionRejecter); ok {
 		if res, rejected := rejecter.RejectBeforePermission(args); rejected {
 			return res

internal/tools/shell_runtime.go

@@ -3,6 +3,7 @@ package tools
 import (
 	"regexp"
 	"strings"
+	"unicode"
 )
 
 type shellRuntime struct {
@@ -17,14 +18,31 @@ type shellIssue struct {
 	Suggestion string
 }
 
+const windowsMsysSandboxKind = "windows_msys_sandbox"
+
+const windowsMsysSandboxSuggestion = "MSYS/Cygwin coreutils from Git for Windows cannot run under Zero's write-restricted Windows sandbox. Prefer Zero native tools (grep, read_file with offset/limit, list_directory, glob), cmd.exe findstr/more, or PowerShell Select-Object -First/-Last. If host-level execution is truly required, rerun with sandbox_permissions: \"require_escalated\" and a narrow justification."
+
+// windowsMsysProneNames is the single source of truth for POSIX coreutil names
+// that commonly resolve to a Git-for-Windows MSYS/Cygwin binary rather than a
+// cmd.exe-native command, and so fail under the write-restricted Windows
+// sandbox (#458). Every Windows MSYS-detection path (the preflight command
+// scan below, the exported MsysProneCommandName, and the known-safe-segment
+// guard in internal/agent/command_prefix.go) derives from this one set, so
+// they cannot drift out of sync with each other.
+var windowsMsysProneNames = map[string]bool{
+	"cat": true, "cut": true, "expr": true, "grep": true, "head": true,
+	"id": true, "ls": true, "nl": true, "paste": true, "rev": true,
+	"seq": true, "stat": true, "tail": true, "tr": true, "uname": true,
+	"uniq": true, "wc": true, "which": true, "awk": true, "sed": true,
+	"xargs": true,
+}
+
 var (
 	windowsBashStyleCDPattern = regexp.MustCompile(`(?i)(^|[&|;]\s*)cd\s+/(?:[a-ce-z0-9_./~-]|d[a-z0-9_./~-])[a-z0-9_./~-]*`)
-	windowsLSCommandPattern   = regexp.MustCompile(`(?i)(^|[&|;]\s*)ls\b(?:\s+|$)`)
-	// windowsPosixUtilityPattern catches the other common POSIX coreutils/grep
-	// family commands cmd.exe has no equivalent for (unlike `dir`/`findstr`,
-	// which sound similar enough that a model might reach for the POSIX name
-	// instead) — most often seen piped in, e.g. `git log ... | head`.
-	windowsPosixUtilityPattern = regexp.MustCompile(`(?i)(^|[&|;]\s*)(head|tail|grep|wc|awk|sed|cut|xargs|tr)(?:\s+|$)`)
+	// windowsMsysBinaryPathPattern catches explicit Git-for-Windows / MSYS usr\bin
+	// paths. These executables are valid Windows PE files but fail under the
+	// write-restricted sandbox with CreateFileMapping ACCESS_DENIED (#458).
+	windowsMsysBinaryPathPattern = regexp.MustCompile(`(?i)(?:\\usr\\bin\\|\\mingw64\\bin\\|msys-2\.0\.dll|cygwin1\.dll)`)
 )
 
 func detectShellRuntime(goos string) shellRuntime {
@@ -37,48 +55,162 @@ func detectShellRuntime(goos string) shellRuntime {
 func shellGuidanceForGOOS(goos string) string {
 	runtime := detectShellRuntime(goos)
 	if goos == "windows" {
-		return "Uses " + runtime.Syntax + " syntax on Windows; prefer cwd over cd when changing directories."
+		return "Uses " + runtime.Syntax + " syntax on Windows; prefer cwd over cd when changing directories. MSYS/Cygwin coreutils on PATH (Git for Windows usr\\bin) are not sandbox-compatible; prefer native Zero file tools."
 	}
 	guidance := "Uses " + runtime.Syntax + " syntax."
 	if goos == "darwin" {
-		// `ps` is setuid root and cannot run under the macOS sandbox; `pgrep` needs a
-		// blocked system service. Point the model at the tools that DO work so it
-		// doesn't waste turns: lsof to find a process, kill to stop it.
 		guidance += " To find or stop a process, use `lsof -i :PORT` (or `lsof -nP -iTCP -sTCP:LISTEN`) for the PID then `kill <pid>`; `ps` and `pgrep` do not work under the sandbox."
 	}
 	return guidance
 }
 
+// MsysProneCommandName reports whether a bare command name commonly resolves to
+// a Git-for-Windows MSYS binary that fails under the Windows restricted sandbox.
+func MsysProneCommandName(name string) bool {
+	return windowsMsysProneNames[strings.ToLower(strings.TrimSpace(name))]
+}
+
+func windowsMsysSandboxIssue(message string) *shellIssue {
+	return &shellIssue{
+		Kind:       windowsMsysSandboxKind,
+		Message:    message,
+		Suggestion: windowsMsysSandboxSuggestion,
+	}
+}
+
+// windowsCommandSegments splits a command into cmd.exe-operator-separated
+// segments (&, |, and their doubled forms &&/||), respecting double quotes
+// (cmd.exe's grouping construct) and the caret (^) escape character, so an
+// operator or command name mentioned inside a quoted argument (e.g. a commit
+// message or PR comment body), or an operator escaped with ^ (cmd.exe prints
+// `echo ^| head` as literal text instead of piping to head), is not mistaken
+// for a real segment boundary or invocation. Unlike bash, cmd.exe does not
+// treat ; as a statement separator, so it is left as ordinary argument text
+// (e.g. `echo foo; head` is a single `echo` invocation with literal args).
+func windowsCommandSegments(command string) []string {
+	var segments []string
+	var current strings.Builder
+	inQuotes := false
+	runes := []rune(command)
+	for i := 0; i < len(runes); i++ {
+		c := runes[i]
+		if !inQuotes && c == '^' && i+1 < len(runes) {
+			current.WriteRune(c)
+			i++
+			current.WriteRune(runes[i])
+			continue
+		}
+		if c == '"' {
+			inQuotes = !inQuotes
+			current.WriteRune(c)
+			continue
+		}
+		if !inQuotes && (c == '&' || c == '|') {
+			if seg := strings.TrimSpace(current.String()); seg != "" {
+				segments = append(segments, seg)
+			}
+			current.Reset()
+			continue
+		}
+		current.WriteRune(c)
+	}
+	if seg := strings.TrimSpace(current.String()); seg != "" {
+		segments = append(segments, seg)
+	}
+	return segments
+}
+
+// firstCommandWord returns the first token of a command segment. A leading
+// double-quoted span counts as one token with its quotes stripped, since
+// cmd.exe treats a quoted path as a single argument: the command invoked by
+// `"C:\Program Files\Git\usr\bin\head.exe" file.txt` is the quoted path, not
+// "C:\Program. For an unquoted command, the token ends at whitespace or a
+// redirection operator (<, >): cmd.exe accepts redirection attached directly
+// to the command name with no separating space (head>out.txt, cat<in.txt), so
+// stopping only at whitespace would return "head>out.txt" as one word and
+// miss the invoked command.
+func firstCommandWord(segment string) string {
+	trimmed := strings.TrimSpace(segment)
+	if trimmed == "" {
+		return ""
+	}
+	if trimmed[0] == '"' {
+		if end := strings.IndexByte(trimmed[1:], '"'); end >= 0 {
+			return trimmed[1 : end+1]
+		}
+		return trimmed[1:]
+	}
+	if end := strings.IndexFunc(trimmed, isCommandWordBoundary); end >= 0 {
+		return trimmed[:end]
+	}
+	return trimmed
+}
+
+func isCommandWordBoundary(r rune) bool {
+	return unicode.IsSpace(r) || r == '<' || r == '>'
+}
+
+// msysProneCommandWord reports whether word (the first token of a command
+// segment, as returned by firstCommandWord) names an MSYS-prone coreutil,
+// bare or with a directory prefix and/or .exe suffix (head, head.exe,
+// C:\...\usr\bin\head.exe, ...).
+func msysProneCommandWord(word string) bool {
+	word = strings.Trim(word, `"`)
+	if i := strings.LastIndexAny(word, `\/`); i >= 0 {
+		word = word[i+1:]
+	}
+	word = strings.TrimSuffix(strings.ToLower(word), ".exe")
+	return MsysProneCommandName(word)
+}
+
 func detectShellCommandIssue(command string, goos string) *shellIssue {
 	if goos != "windows" {
 		return nil
 	}
 	trimmed := strings.TrimSpace(command)
-	if windowsBashStyleCDPattern.MatchString(trimmed) ||
-		windowsLSCommandPattern.MatchString(trimmed) {
+	if windowsBashStyleCDPattern.MatchString(trimmed) {
 		return &shellIssue{
 			Kind:       "windows_shell_syntax",
 			Message:    "Command looks like POSIX/Bash syntax, but Zero runs bash tool commands through Windows cmd.exe on this host.",
 			Suggestion: "Use the cwd argument instead of cd, use Windows cmd.exe syntax, or use native tools such as list_directory, read_file, grep, and glob.",
 		}
 	}
-	if windowsPosixUtilityPattern.MatchString(trimmed) {
-		return &shellIssue{
-			Kind:       "windows_shell_syntax",
-			Message:    "Command uses a POSIX utility (head/tail/grep/wc/awk/sed/cut/xargs/tr) that Windows cmd.exe does not have.",
-			Suggestion: "Use cmd.exe equivalents (e.g. `findstr` for grep, `more` to page output) or Zero's native tools (grep, read_file with offset/limit) instead of piping to a POSIX utility.",
+	// Check the first word of each operator-separated segment (not the raw
+	// text anywhere in the command) against the MSYS binary-path pattern and
+	// the single MSYS-prone name set, covering bare names (head), .exe names
+	// (head.exe), and directory-prefixed forms (C:\...\head.exe) uniformly.
+	// Being segment/word anchored rather than a whole-string regex or scan,
+	// neither check matches text that only appears inside a quoted argument
+	// (e.g. a commit message or PR comment body discussing head.exe).
+	for _, segment := range windowsCommandSegments(trimmed) {
+		word := firstCommandWord(segment)
+		if windowsMsysBinaryPathPattern.MatchString(word) {
+			return windowsMsysSandboxIssue("Command invokes an MSYS/Cygwin binary path that cannot run under Zero's Windows sandbox.")
+		}
+		if msysProneCommandWord(word) {
+			return windowsMsysSandboxIssue("Command uses a POSIX coreutil (head/tail/grep/cat/...) that commonly resolves to Git-for-Windows MSYS binaries incompatible with the Windows sandbox.")
 		}
 	}
 	return nil
 }
 
-func detectShellOutputIssue(command string, output string, goos string) *shellIssue {
+// detectShellOutputIssue looks for MSYS runtime crash markers and cmd.exe
+// syntax-error text in output only, never in the command that was run. The
+// command line is attacker/user-controlled argument text (e.g. a `gh pr
+// comment --body` quoting a sample failure), not something the shell
+// produced, so treating it as evidence would reintroduce the same
+// quoted-text false positives the preflight command-position check exists to
+// avoid, just after execution instead of before it.
+func detectShellOutputIssue(output string, goos string) *shellIssue {
 	if goos != "windows" {
 		return nil
 	}
-	haystack := strings.ToLower(command + "\n" + output)
-	if strings.Contains(haystack, "the syntax of the command is incorrect") ||
-		strings.Contains(haystack, "is not recognized as an internal or external command") {
+	lower := strings.ToLower(output)
+	if msysRuntimeFailedInOutput(lower) {
+		return windowsMsysSandboxIssue("An MSYS/Cygwin runtime failed under Zero's Windows sandbox (ACCESS_DENIED during MSYS startup).")
+	}
+	if strings.Contains(lower, "the syntax of the command is incorrect") ||
+		strings.Contains(lower, "is not recognized as an internal or external command") {
 		return &shellIssue{
 			Kind:       "windows_shell_syntax",
 			Message:    "Windows cmd.exe rejected the command syntax.",
@@ -88,6 +220,32 @@ func detectShellOutputIssue(command string, output string, goos string) *shellIs
 	return nil
 }
 
+func msysRuntimeFailedInOutput(lower string) bool {
+	if strings.Contains(lower, "fatal error - createfilemapping") {
+		return true
+	}
+	if strings.Contains(lower, "couldn't create signal pipe") && strings.Contains(lower, "win32 error 5") {
+		return true
+	}
+	if strings.Contains(lower, "cygheap_user::init") && strings.Contains(lower, "fatal error") {
+		return true
+	}
+	if strings.Contains(lower, "usr\\bin\\") && strings.Contains(lower, "fatal error") {
+		return true
+	}
+	if !strings.Contains(lower, "win32 error 5") || !strings.Contains(lower, "terminating") {
+		return false
+	}
+	// Anchor the broad win32-error-5 fallback to an MSYS-specific marker so
+	// unrelated access-denied failures are not mislabeled as MSYS sandbox
+	// incompatibilities.
+	return strings.Contains(lower, `usr\bin\`) ||
+		strings.Contains(lower, "cygheap") ||
+		strings.Contains(lower, "msys-2.0.dll") ||
+		strings.Contains(lower, "cygwin1.dll") ||
+		strings.Contains(lower, "[main]")
+}
+
 func appendShellIssueHint(output string, issue shellIssue) string {
 	output = strings.TrimRight(output, "\r\n")
 	hint := "[zero] shell issue: " + issue.Message

internal/tools/shell_runtime_test.go

@@ -0,0 +1,208 @@
+package tools
+
+import (
+	"strings"
+	"testing"
+)
+
+func TestDetectShellCommandIssueFlagsMsysBinaryPaths(t *testing.T) {
+	for _, command := range []string{
+		`for /F %i in ('whoami') do echo %i | "C:\Program Files\Git\usr\bin\head.exe" -1`,
+		`C:\Git\usr\bin\grep.exe pattern file.txt`,
+	} {
+		issue := detectShellCommandIssue(command, "windows")
+		if issue == nil {
+			t.Fatalf("expected MSYS path issue for %q", command)
+		}
+		if issue.Kind != "windows_msys_sandbox" {
+			t.Fatalf("expected windows_msys_sandbox kind, got %q", issue.Kind)
+		}
+		if !strings.Contains(issue.Suggestion, "require_escalated") {
+			t.Fatalf("expected escalation guidance, got %#v", issue)
+		}
+	}
+}
+
+func TestDetectShellCommandIssueFlagsStandaloneCat(t *testing.T) {
+	issue := detectShellCommandIssue(`cat README.md`, "windows")
+	if issue == nil || issue.Kind != "windows_msys_sandbox" {
+		t.Fatalf("expected MSYS sandbox issue for cat, got %#v", issue)
+	}
+}
+
+func TestDetectShellOutputIssueFlagsMsysCreateFileMappingError(t *testing.T) {
+	output := `0 [main] head (3568) C:\Program Files\Git\usr\bin\head.exe: *** fatal error - CreateFileMapping S-1-5-21-3149109338-1484423945-518236903-1001.1, Win32 error 5.  Terminating.`
+	issue := detectShellOutputIssue(output, "windows")
+	if issue == nil || issue.Kind != "windows_msys_sandbox" {
+		t.Fatalf("expected MSYS output issue, got %#v", issue)
+	}
+	if !strings.Contains(issue.Suggestion, "require_escalated") {
+		t.Fatalf("expected escalation guidance, got %#v", issue)
+	}
+}
+
+func TestDetectShellOutputIssueFlagsMsysSignalPipeError(t *testing.T) {
+	output := `0 [main] head (39684) cygheap_user::init: NtSetInformationToken (TokenDefaultDacl), 0xC0000022
+648 [main] head (39684) C:\Program Files\Git\usr\bin\head.exe: *** fatal error - couldn't create signal pipe, Win32 error 5`
+	issue := detectShellOutputIssue(output, "windows")
+	if issue == nil || issue.Kind != "windows_msys_sandbox" {
+		t.Fatalf("expected MSYS output issue, got %#v", issue)
+	}
+}
+
+func TestDetectShellOutputIssueFlagsMsysTerminatingWithMsysMarker(t *testing.T) {
+	output := `1 [main] tail (4321) tail: *** MapViewOfFileEx failed, Win32 error 5.  Terminating.`
+	issue := detectShellOutputIssue(output, "windows")
+	if issue == nil || issue.Kind != "windows_msys_sandbox" {
+		t.Fatalf("expected MSYS output issue, got %#v", issue)
+	}
+}
+
+func TestDetectShellOutputIssueIgnoresNonMsysWin32Error5(t *testing.T) {
+	output := `myapp.exe: unable to open service handle, Win32 error 5 (access denied). Terminating worker.`
+	issue := detectShellOutputIssue(output, "windows")
+	if issue != nil {
+		t.Fatalf("expected no issue for non-MSYS access-denied output, got %#v", issue)
+	}
+}
+
+func TestShellIssueBlockResultMsysCommand(t *testing.T) {
+	result := shellIssueBlockResult(*detectShellCommandIssue(`cat README.md`, "windows"))
+	if result.Status != StatusError {
+		t.Fatalf("status = %q, want error", result.Status)
+	}
+	for _, want := range []string{"[zero] shell issue:", "MSYS/Cygwin", "grep", "read_file", "require_escalated"} {
+		if !strings.Contains(result.Output, want) {
+			t.Fatalf("expected %q in blocked output, got %q", want, result.Output)
+		}
+	}
+	if result.Meta["shell_issue"] != "windows_msys_sandbox" {
+		t.Fatalf("meta shell_issue = %q", result.Meta["shell_issue"])
+	}
+}
+
+func TestMsysProneCommandName(t *testing.T) {
+	if !MsysProneCommandName("HEAD") || MsysProneCommandName("echo") {
+		t.Fatalf("unexpected MsysProneCommandName results")
+	}
+}
+
+// TestDetectShellCommandIssueFlagsExprAndLsConsistently guards against the
+// preflight regex list drifting from the canonical windowsMsysProneNames set
+// (both listed expr and ls as MSYS-prone, but the old regex alternations
+// omitted expr entirely and let ls hit the older windows_shell_syntax branch
+// first, so it never got MSYS-kind guidance).
+func TestDetectShellCommandIssueFlagsExprAndLsConsistently(t *testing.T) {
+	for _, command := range []string{
+		`expr 1 + 1`,
+		`expr.exe 1 + 1`,
+		`ls -la`,
+		`ls`,
+	} {
+		issue := detectShellCommandIssue(command, "windows")
+		if issue == nil || issue.Kind != windowsMsysSandboxKind {
+			t.Fatalf("expected windows_msys_sandbox for %q, got %#v", command, issue)
+		}
+	}
+}
+
+// TestDetectShellCommandIssueIgnoresQuotedMsysMentions guards against
+// treating an MSYS-prone name that only appears inside a quoted argument
+// (e.g. a commit message, a PR comment body, or a doc string discussing the
+// command) as an actual invocation. The preflight check must anchor on the
+// first word of each command segment, not scan the raw text anywhere.
+func TestDetectShellCommandIssueIgnoresQuotedMsysMentions(t *testing.T) {
+	for _, command := range []string{
+		`git commit -m "fix head.exe crash"`,
+		`gh pr comment --body "grep.exe fails under MSYS"`,
+		`echo "log | head is broken on windows"`,
+		`git commit -m "note: | head does not work here"`,
+	} {
+		if issue := detectShellCommandIssue(command, "windows"); issue != nil {
+			t.Fatalf("expected quoted MSYS mention to pass for %q, got %#v", command, issue)
+		}
+	}
+
+	// A real invocation alongside quoted text must still be caught.
+	if issue := detectShellCommandIssue(`echo "not a real command" && head file.txt`, "windows"); issue == nil || issue.Kind != windowsMsysSandboxKind {
+		t.Fatalf("expected real head invocation to still be flagged, got %#v", issue)
+	}
+}
+
+// TestDetectShellCommandIssueIgnoresQuotedMsysPathMentions guards the
+// explicit MSYS-binary-path check the same way as the coreutil-name check:
+// a full usr\bin\ path that only appears inside a quoted argument (e.g. a
+// commit message describing the failure) must not be treated as an
+// invocation, since the path check is now anchored to the first word of each
+// command segment rather than scanned across the raw command text.
+func TestDetectShellCommandIssueIgnoresQuotedMsysPathMentions(t *testing.T) {
+	for _, command := range []string{
+		`git commit -m "C:\Program Files\Git\usr\bin\head.exe fails"`,
+		`gh pr comment --body "C:\Git\usr\bin\grep.exe is blocked"`,
+	} {
+		if issue := detectShellCommandIssue(command, "windows"); issue != nil {
+			t.Fatalf("expected quoted MSYS path mention to pass for %q, got %#v", command, issue)
+		}
+	}
+
+	// A real invocation by full path must still be caught.
+	if issue := detectShellCommandIssue(`C:\Git\usr\bin\grep.exe pattern file.txt`, "windows"); issue == nil || issue.Kind != windowsMsysSandboxKind {
+		t.Fatalf("expected real MSYS path invocation to still be flagged, got %#v", issue)
+	}
+}
+
+// TestDetectShellCommandIssueRespectsCaretEscapedOperators guards against
+// misreading cmd.exe's ^ escape character: `echo ^| head` prints the pipe and
+// "head" as literal text (the caret escapes the pipe so it never splits into
+// a separate `head` invocation), and `echo foo; head` is a single `echo`
+// command with literal arguments since cmd.exe (unlike bash) does not treat
+// ; as a statement separator.
+func TestDetectShellCommandIssueRespectsCaretEscapedOperators(t *testing.T) {
+	for _, command := range []string{
+		`echo ^| head`,
+		`echo ^& head`,
+		`echo foo; head`,
+	} {
+		if issue := detectShellCommandIssue(command, "windows"); issue != nil {
+			t.Fatalf("expected no issue for %q, got %#v", command, issue)
+		}
+	}
+
+	// An unescaped pipe must still split into a real head invocation.
+	if issue := detectShellCommandIssue(`echo foo | head`, "windows"); issue == nil || issue.Kind != windowsMsysSandboxKind {
+		t.Fatalf("expected real head invocation to still be flagged, got %#v", issue)
+	}
+}
+
+// TestDetectShellCommandIssueFlagsRedirectionAttachedToCommand guards against
+// firstCommandWord treating cmd.exe redirection operators as part of the
+// command name. cmd.exe accepts redirection with no separating space
+// (head>out.txt, cat<in.txt), so splitting only on whitespace would return
+// "head>out.txt" as one word and miss the invoked command entirely.
+func TestDetectShellCommandIssueFlagsRedirectionAttachedToCommand(t *testing.T) {
+	for _, command := range []string{
+		`some-command | head>out.txt`,
+		`cat<in.txt`,
+		`grep>matches.txt pattern`,
+	} {
+		issue := detectShellCommandIssue(command, "windows")
+		if issue == nil || issue.Kind != windowsMsysSandboxKind {
+			t.Fatalf("expected windows_msys_sandbox for %q, got %#v", command, issue)
+		}
+	}
+}
+
+// TestDetectShellOutputIssueSignatureOmitsCommandText documents, at the type
+// level, that detectShellOutputIssue can no longer take the command line as
+// evidence: it only accepts the real output. Harmless output must not be
+// flagged, and output that genuinely carries the MSYS failure markers must
+// still be flagged.
+func TestDetectShellOutputIssueSignatureOmitsCommandText(t *testing.T) {
+	if issue := detectShellOutputIssue("hello from bash", "windows"); issue != nil {
+		t.Fatalf("expected no issue for harmless output, got %#v", issue)
+	}
+	output := `0 [main] head (3568) C:\Program Files\Git\usr\bin\head.exe: *** fatal error - CreateFileMapping ..., Win32 error 5.  Terminating.`
+	if issue := detectShellOutputIssue(output, "windows"); issue == nil || issue.Kind != windowsMsysSandboxKind {
+		t.Fatalf("expected real MSYS output to still be flagged, got %#v", issue)
+	}
+}

internal/tools/spill.go

@@ -8,6 +8,7 @@ import (
 	"time"
 
 	"github.com/Gitlawb/zero/internal/redaction"
+	"github.com/Gitlawb/zero/internal/secrets"
 )
 
 // Spill-to-disk for truncated tool output. When a command produces more than
@@ -90,8 +91,10 @@ func spillDir() (string, error) {
 // spillTruncatedOutput writes the full pre-truncation output to the spill
 // directory and returns the file path, or "" when spilling fails. Output is
 // scrubbed with the same configured-key redaction the registry applies at the
-// tool boundary, so a spilled file never holds a secret the transcript would
-// have hidden.
+// tool boundary PLUS the pattern-based secret scanner (AWS keys, tokens, PEM
+// blocks, JWTs) that bash applies to its model-visible output — a spill runs
+// before that formatter, so without the scan here a spilled file would hold
+// pattern-matched credentials in cleartext that the transcript hides.
 func spillTruncatedOutput(toolName, output string) string {
 	dir, err := spillDir()
 	if err != nil {
@@ -110,6 +113,7 @@ func spillTruncatedOutput(toolName, output string) string {
 	}
 	defer file.Close()
 	scrubbed := redaction.RedactString(output, redaction.Options{})
+	scrubbed, _ = secrets.Redact(scrubbed)
 	if _, err := file.WriteString(scrubbed); err != nil {
 		_ = os.Remove(file.Name())
 		return ""

internal/tools/spill_test.go

@@ -63,6 +63,33 @@ func TestSweepSpillDirRemovesOnlyOldFiles(t *testing.T) {
 	}
 }
 
+// A spill happens BEFORE bash's model-facing formatter runs its pattern-based
+// secret scan, so the spill itself must scrub pattern-matched credentials —
+// otherwise the file would hold in cleartext exactly what the transcript hides.
+func TestSpillTruncatedOutputScrubsPatternSecrets(t *testing.T) {
+	setTestTempDir(t)
+	githubToken := "ghp_" + strings.Repeat("a", 36)
+	body := "before\nAKIAIOSFODNN7EXAMPLE\n" + githubToken + "\nafter"
+
+	path := spillTruncatedOutput("bash", body)
+	if path == "" {
+		t.Fatal("spill must return a file path")
+	}
+	content, err := os.ReadFile(path)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if strings.Contains(string(content), "AKIAIOSFODNN7EXAMPLE") {
+		t.Fatal("AWS access key reached the spill file in cleartext")
+	}
+	if strings.Contains(string(content), githubToken) {
+		t.Fatal("GitHub token reached the spill file in cleartext")
+	}
+	if !strings.Contains(string(content), "before") || !strings.Contains(string(content), "after") {
+		t.Fatalf("non-secret content must survive the scrub: %q", content)
+	}
+}
+
 func TestSpillTruncatedOutputWritesFile(t *testing.T) {
 	t.Setenv("TMPDIR", t.TempDir())
 	path := spillTruncatedOutput("exec_command", "some output body")

internal/tools/web_fetch.go

@@ -28,7 +28,7 @@ const (
 	webFetchTimeout         = 30 * time.Second
 	webFetchRedirectLimit   = 5
 	webFetchErrorBodyLimit  = 4 * 1024
-	webFetchPublicOnlyHint  = "web_fetch only supports public remote HTTP/HTTPS URLs. For localhost or private network URLs, use bash with curl so sandbox network permission can apply."
+	webFetchPublicOnlyHint  = "web_fetch only supports public remote HTTP/HTTPS URLs. For localhost or private network URLs, use bash with curl so sandbox network permission can apply"
 )
 
 type webFetchTool struct {
@@ -348,7 +348,7 @@ func webFetchRedirectPolicy(previous func(*http.Request, []*http.Request) error,
 			return fmt.Errorf("too many redirects: maximum is %d", webFetchRedirectLimit)
 		}
 		if err := validateParsedWebFetchURL(request.Context(), request.URL, resolver); err != nil {
-			return fmt.Errorf("Unsafe redirect URL: %w", err)
+			return fmt.Errorf("unsafe redirect URL: %w", err)
 		}
 		if previous != nil {
 			return previous(request, via)

internal/tools/web_fetch_test.go

@@ -405,7 +405,7 @@ func TestWebFetchToolRejectsUnsafeRedirects(t *testing.T) {
 			if result.Status != StatusError {
 				t.Fatalf("expected redirect safety error, got %s: %s", result.Status, result.Output)
 			}
-			if !strings.Contains(result.Output, "Unsafe redirect URL") {
+			if !strings.Contains(result.Output, "unsafe redirect URL") {
 				t.Fatalf("expected unsafe redirect message, got %q", result.Output)
 			}
 		})

internal/tools/web_search.go

@@ -426,7 +426,6 @@ func stringListArgWebSearch(args map[string]any, key string) (domains []string,
 	if !ok || value == nil {
 		return nil, false, nil
 	}
-	provided = true
 	raw, ok := value.([]any)
 	if !ok {
 		if asString, ok2 := value.([]string); ok2 {

internal/tui/autocomplete.go

@@ -188,7 +188,54 @@ func (m model) matchCommandSuggestions(token string) []commandSuggestion {
 	out := matchCommandSuggestionsWithFilter(token, func(command commandDefinition) bool {
 		return command.kind != commandSandboxSetup || m.sandboxSetupCommand != nil
 	})
-	return append(out, m.matchUserCommandSuggestions(token)...)
+	out = append(out, m.matchUserCommandSuggestions(token)...)
+	out = append(out, m.matchSkillSuggestions(token)...)
+	// Each source caps itself, but the merged list must honor the shared cap too
+	// (three sources could otherwise stack up to ~3x the palette bound).
+	if len(out) > maxCommandSuggestions {
+		out = out[:maxCommandSuggestions]
+	}
+	return out
+}
+
+// matchSkillSuggestions returns installed skills whose slash name has the typed
+// prefix, so skills are discoverable and invocable from the palette like user
+// commands. Precedence (builtin > user command > skill) is enforced here by
+// skipping any skill whose name is claimed by a builtin (or alias) or a user
+// command — unlike the builtin/user pair, a shadowed skill row would be dead at
+// dispatch time, so it must not be advertised at all.
+func (m model) matchSkillSuggestions(token string) []commandSuggestion {
+	prefix := strings.ToLower(strings.TrimSpace(strings.TrimPrefix(token, "/")))
+	if prefix == "" || m.loadSkills == nil {
+		return nil
+	}
+	taken := m.takenSlashNames()
+	var out []commandSuggestion
+	// Read through the loader (not the startup snapshot in agentOptions) so the
+	// palette matches what dispatch will actually resolve — a skill installed or
+	// removed mid-session appears/disappears without a restart.
+	for _, skill := range m.installedSkills() {
+		name := skillSlashName(skill.Name)
+		if name == "" || taken[name] || !strings.HasPrefix(name, prefix) {
+			continue
+		}
+		// Two skills whose names collide after lowercasing (e.g. "Deploy" and
+		// "deploy") map to one slash name; only the first — the one dispatch will
+		// run — may be advertised, or the row's description and the executed
+		// instructions silently diverge.
+		taken[name] = true
+		desc := strings.TrimSpace(skill.Description)
+		if desc == "" {
+			desc = "Skill: /" + name
+		} else {
+			desc += " (skill)"
+		}
+		out = append(out, commandSuggestion{Name: "/" + name, Desc: desc})
+		if len(out) >= maxCommandSuggestions {
+			break
+		}
+	}
+	return out
 }
 
 // matchUserCommandSuggestions returns file-sourced /commands whose name has the

internal/tui/command_views.go

@@ -698,3 +698,19 @@ func (m model) debugText() string {
 		}},
 	})
 }
+
+// skillsText is the /skills fallback when NO skills are installed — an install
+// hint. With skills present /skills opens the searchable skill picker instead
+// (see newSkillPicker), matching how /model works.
+func (m model) skillsText() string {
+	return renderCommandOutput(commandOutput{
+		Title:  "Skills",
+		Status: commandStatusInfo,
+		Sections: []commandSection{{
+			Lines: []string{"No skills installed."},
+		}},
+		Hints: []string{
+			"install one: create <skills-dir>/<name>/SKILL.md (see `zero skills`)",
+		},
+	})
+}

internal/tui/commands.go

@@ -46,6 +46,8 @@ const (
 	commandCopy
 	commandExport
 	commandNew
+	commandSkills
+	commandLoop
 	commandUnknown
 )
 
@@ -131,6 +133,13 @@ var commandDefinitions = []commandDefinition{
 		description: "List registered tools.",
 		kind:        commandTools,
 	},
+	{
+		name:        "/skills",
+		usage:       "/skills",
+		group:       commandGroupTools,
+		description: "List installed skills; run one directly with /<skill-name> [args].",
+		kind:        commandSkills,
+	},
 	{
 		name:        "/context",
 		usage:       "/context",
@@ -289,6 +298,13 @@ var commandDefinitions = []commandDefinition{
 		description: "Write the conversation transcript to a file.",
 		kind:        commandExport,
 	},
+	{
+		name:        "/loop",
+		usage:       "/loop [interval] <prompt|/command> | /loop list | /loop stop [id|all]",
+		group:       commandGroupSession,
+		description: "Repeat a prompt or command on an interval (e.g. /loop 5m /babysit-prs), or self-paced when no interval is given.",
+		kind:        commandLoop,
+	},
 	{
 		name:        "/help",
 		usage:       "/help",

internal/tui/loop.go

@@ -0,0 +1,693 @@
+package tui
+
+import (
+	"fmt"
+	"regexp"
+	"strconv"
+	"strings"
+	"time"
+
+	tea "charm.land/bubbletea/v2"
+)
+
+// The /loop command repeats a prompt or slash command in one of two modes:
+//
+//   - Fixed interval — `/loop 5m <prompt>` re-fires on a wall-clock cadence.
+//   - Self-paced     — bare `/loop <prompt>` runs a maintenance playbook: the model
+//     does one increment of work each iteration and ends its reply with a control
+//     line (`LOOP: DONE` / `LOOP: CONTINUE [interval]`) that stops the loop or picks
+//     the next wake. With no control line it falls back to an adaptive cadence.
+//
+// Loops are foreground and session-scoped: a tick only fires while the session is
+// idle between turns (it never interrupts a streaming turn), the loop lives with the
+// session that created it, and switching sessions (/new, /resume) stops it. Safety
+// rails cap iterations, age, consecutive failures, and no-progress repetition.
+// Everything here is pure/loop-local; the turn-lifecycle wiring (ticker, launch,
+// continuation) lives in model.go.
+
+type loopMode int
+
+const (
+	loopModeFixed     loopMode = iota // re-fire every fixed interval
+	loopModeSelfPaced                 // model chooses the next wake each iteration
+)
+
+// Safety bounds. A loop is foreground + session-scoped, but these keep a runaway
+// or forgotten loop from burning tokens forever.
+const (
+	loopMinInterval   = 30 * time.Second
+	loopMaxInterval   = 24 * time.Hour
+	loopMaxIterations = 500 // hard ceiling; the loop auto-stops after this many
+
+	// loopMaxAge auto-expires a loop this long after it was created, so a forgotten
+	// loop stops on its own even if it never reaches the iteration cap.
+	loopMaxAge = 24 * time.Hour
+
+	loopSelfPaceMin     = 1 * time.Minute
+	loopSelfPaceMax     = 1 * time.Hour
+	loopSelfPaceDefault = 15 * time.Minute
+
+	// loopDoomThreshold ends a loop after this many consecutive identical final
+	// answers — a self-paced or interval loop that gets stuck repeating the same
+	// no-progress result should stop rather than churn.
+	loopDoomThreshold = 5
+
+	// loopMaxFailures ends a loop after this many consecutive failed iterations, so
+	// a loop whose iterations keep erroring stops instead of churning to the
+	// iteration cap (a failed turn has no final answer, so the doom guard can't see
+	// the lack of progress).
+	loopMaxFailures = 3
+
+	// loopPollInterval is how often the controller checks whether a loop is due.
+	// A loop only fires while idle, so this is a cheap between-turn poll.
+	loopPollInterval = 1 * time.Second
+)
+
+// loopState is one active loop owned by the current session.
+type loopState struct {
+	id        string
+	mode      loopMode
+	prompt    string // the prompt or "/command" re-run each iteration
+	interval  time.Duration
+	iteration int
+	maxIter   int // 0 => loopMaxIterations
+	createdAt time.Time
+	nextRunAt time.Time
+	// lastResult / repeatRun drive doom-loop detection: consecutive identical
+	// final answers past loopDoomThreshold end the loop.
+	lastResult string
+	repeatRun  int
+	// failRun counts consecutive failed iterations; past loopMaxFailures the loop
+	// stops (a failed turn has no final answer for the doom guard to compare).
+	failRun int
+	paused  bool
+}
+
+func (l *loopState) iterationCap() int {
+	if l.maxIter > 0 {
+		return l.maxIter
+	}
+	return loopMaxIterations
+}
+
+// due reports whether the loop should fire at now (active, not paused, past its
+// next-run mark).
+func (l *loopState) due(now time.Time) bool {
+	return !l.paused && !l.nextRunAt.IsZero() && !now.Before(l.nextRunAt)
+}
+
+// cadenceText renders the loop's cadence for status lines.
+func (l *loopState) cadenceText() string {
+	if l.mode == loopModeSelfPaced {
+		return "self-paced"
+	}
+	return "every " + formatLoopDuration(l.interval)
+}
+
+type loopAction int
+
+const (
+	loopActionUsage   loopAction = iota // show usage / list when empty
+	loopActionStart                     // start a new loop
+	loopActionStop                      // stop one by id
+	loopActionStopAll                   // stop every loop
+	loopActionList                      // list active loops
+)
+
+// loopCommand is the parsed form of a `/loop ...` invocation (the text after the
+// command name).
+type loopCommand struct {
+	action   loopAction
+	targetID string
+	mode     loopMode
+	prompt   string
+	interval time.Duration
+	// note carries a non-fatal advisory (e.g. an interval that was clamped) to
+	// surface back to the user.
+	note string
+}
+
+var loopIntervalRe = regexp.MustCompile(`^(\d+)(s|m|h|d)$`)
+
+// loopControlRe matches a self-paced loop's control line at the start of a line,
+// tolerant of a leading markdown bullet/quote marker and any trailing note after
+// the keyword: "LOOP: DONE", "- loop: continue", "LOOP: CONTINUE 10m — still tidying".
+// The leading ^ anchor keeps a mid-sentence mention ("I'll emit LOOP: DONE when…")
+// from matching; parseLoopControl normalizes CRLF first so `$` can reach line end.
+var loopControlRe = regexp.MustCompile(`(?im)^[^\S\r\n]*(?:[-*>•][^\S\r\n]*)?loop:[^\S\r\n]*(done|continue)\b(?:[^\S\r\n]+(\d+[smhd])\b)?.*$`)
+
+// parseLoopCommand interprets the arguments to `/loop`. Forms:
+//
+//	(empty)                 -> usage/list
+//	list | status          -> list active loops
+//	stop | stop all | stop <id>
+//	<interval> <prompt>     -> fixed-interval loop (e.g. "5m /babysit")
+//	<prompt> every <interval>
+//	<prompt>                -> self-paced loop (no interval)
+func parseLoopCommand(args string) loopCommand {
+	trimmed := strings.TrimSpace(args)
+	if trimmed == "" {
+		return loopCommand{action: loopActionUsage}
+	}
+
+	first := strings.ToLower(strings.Fields(trimmed)[0])
+	switch first {
+	case "list", "status", "ls":
+		return loopCommand{action: loopActionList}
+	case "stop", "cancel", "kill":
+		rest := strings.TrimSpace(trimmed[len(strings.Fields(trimmed)[0]):])
+		if rest == "" || strings.EqualFold(rest, "all") {
+			if strings.EqualFold(rest, "all") {
+				return loopCommand{action: loopActionStopAll}
+			}
+			// bare "stop" stops all when ambiguous; the caller may special-case a
+			// single active loop.
+			return loopCommand{action: loopActionStop, targetID: ""}
+		}
+		return loopCommand{action: loopActionStop, targetID: strings.TrimSpace(rest)}
+	}
+
+	// Leading interval token: "5m <prompt>".
+	if fields := strings.Fields(trimmed); len(fields) >= 2 {
+		if d, ok := parseLoopInterval(fields[0]); ok {
+			prompt := strings.TrimSpace(trimmed[len(fields[0]):])
+			cmd := loopCommand{action: loopActionStart, mode: loopModeFixed, prompt: prompt}
+			cmd.interval, cmd.note = clampLoopInterval(d)
+			return cmd
+		}
+	}
+
+	// Trailing "every <interval>".
+	if prompt, d, ok := splitTrailingEvery(trimmed); ok {
+		cmd := loopCommand{action: loopActionStart, mode: loopModeFixed, prompt: prompt}
+		cmd.interval, cmd.note = clampLoopInterval(d)
+		return cmd
+	}
+
+	// No interval anywhere -> self-paced.
+	return loopCommand{action: loopActionStart, mode: loopModeSelfPaced, prompt: trimmed}
+}
+
+// splitTrailingEvery matches "<prompt> every <interval>" (the interval must be a
+// real duration token so "check every PR" is not mis-parsed as a cadence).
+func splitTrailingEvery(input string) (string, time.Duration, bool) {
+	fields := strings.Fields(input)
+	if len(fields) < 3 {
+		return "", 0, false
+	}
+	last := fields[len(fields)-1]
+	prev := fields[len(fields)-2]
+	if !strings.EqualFold(prev, "every") {
+		return "", 0, false
+	}
+	d, ok := parseLoopInterval(last)
+	if !ok {
+		return "", 0, false
+	}
+	prompt := strings.TrimSpace(strings.Join(fields[:len(fields)-2], " "))
+	if prompt == "" {
+		return "", 0, false
+	}
+	return prompt, d, true
+}
+
+// parseLoopInterval parses a bare "<N><unit>" token (s/m/h/d) into a duration.
+func parseLoopInterval(token string) (time.Duration, bool) {
+	m := loopIntervalRe.FindStringSubmatch(strings.ToLower(strings.TrimSpace(token)))
+	if m == nil {
+		return 0, false
+	}
+	n, err := strconv.Atoi(m[1])
+	if err != nil || n <= 0 {
+		return 0, false
+	}
+	unit := map[string]time.Duration{
+		"s": time.Second,
+		"m": time.Minute,
+		"h": time.Hour,
+		"d": 24 * time.Hour,
+	}[m[2]]
+	return time.Duration(n) * unit, true
+}
+
+// clampLoopInterval bounds an interval to [loopMinInterval, loopMaxInterval] and
+// returns an advisory note when it was adjusted.
+func clampLoopInterval(d time.Duration) (time.Duration, string) {
+	switch {
+	case d < loopMinInterval:
+		return loopMinInterval, fmt.Sprintf("interval raised to the %s minimum", formatLoopDuration(loopMinInterval))
+	case d > loopMaxInterval:
+		return loopMaxInterval, fmt.Sprintf("interval lowered to the %s maximum", formatLoopDuration(loopMaxInterval))
+	default:
+		return d, ""
+	}
+}
+
+// loopTickMsg is the between-turn poll that fires a due loop while the session is
+// idle. seq invalidates a tick left over from before the loop set changed.
+type loopTickMsg struct{ seq int }
+
+// handleLoopCommand dispatches a parsed `/loop ...` invocation.
+func (m model) handleLoopCommand(args string) (model, tea.Cmd) {
+	cmd := parseLoopCommand(args)
+	switch cmd.action {
+	case loopActionList:
+		return m.appendLoopSystem(m.loopListText()), nil
+	case loopActionUsage:
+		if len(m.loops) > 0 {
+			return m.appendLoopSystem(m.loopListText()), nil
+		}
+		return m.appendLoopSystem(loopUsageText()), nil
+	case loopActionStop:
+		return m.stopLoop(cmd.targetID)
+	case loopActionStopAll:
+		return m.stopAllLoops()
+	case loopActionStart:
+		return m.startLoop(cmd)
+	}
+	return m, nil
+}
+
+// startLoop registers a new loop and (re)starts the idle poll ticker. The first
+// iteration fires on the next idle tick (nextRunAt = now).
+func (m model) startLoop(cmd loopCommand) (model, tea.Cmd) {
+	if reason, ok := m.validateLoopTarget(cmd.prompt); !ok {
+		return m.appendLoopSystem(reason), nil
+	}
+	// A /command loop must be fixed-interval. Self-paced mode drives a free-form
+	// goal through the playbook + LOOP: control line (see firePrompt), which a
+	// custom command's expanded template never carries — so a bare self-paced
+	// /command would silently degrade to adaptive polling with no way to report
+	// done. Require an explicit interval for command loops instead.
+	if cmd.mode == loopModeSelfPaced && strings.HasPrefix(strings.TrimSpace(cmd.prompt), "/") {
+		return m.appendLoopSystem("A /command loop needs an interval — e.g. /loop 5m " + strings.Fields(cmd.prompt)[0] + ". Self-paced mode (no interval) is for a free-form goal."), nil
+	}
+	m.loopCounter++
+	id := "L" + strconv.Itoa(m.loopCounter)
+	loop := &loopState{
+		id:        id,
+		mode:      cmd.mode,
+		prompt:    cmd.prompt,
+		interval:  cmd.interval,
+		createdAt: m.now(),
+		nextRunAt: m.now(), // fire the first iteration on the next idle tick
+	}
+	m.loops = append(m.loops, loop)
+	note := ""
+	if cmd.note != "" {
+		note = " (" + cmd.note + ")"
+	}
+	m = m.appendLoopSystem(fmt.Sprintf(
+		"Loop %s started — %s%s. Runs while this session is idle; stop with /loop stop %s.",
+		id, loop.cadenceText(), note, id))
+	return m.ensureLoopTick()
+}
+
+// stopLoop stops one loop by id, or the single active loop when the id is omitted.
+func (m model) stopLoop(id string) (model, tea.Cmd) {
+	if len(m.loops) == 0 {
+		return m.appendLoopSystem("No active loops."), nil
+	}
+	if id == "" {
+		if len(m.loops) == 1 {
+			return m.removeLoop(m.loops[0].id, "Loop "+m.loops[0].id+" stopped.").ensureLoopTick()
+		}
+		return m.appendLoopSystem("Multiple loops active — use /loop stop <id> or /loop stop all.\n" + m.loopListText()), nil
+	}
+	if m.findLoop(id) == nil {
+		return m.appendLoopSystem("No loop " + id + ". " + m.loopListText()), nil
+	}
+	// removeLoop stops the poll ticker; re-arm it so any OTHER loops that remain
+	// keep firing (ensureLoopTick no-ops when this was the last loop).
+	return m.removeLoop(id, "Loop "+id+" stopped.").ensureLoopTick()
+}
+
+func (m model) stopAllLoops() (model, tea.Cmd) {
+	if len(m.loops) == 0 {
+		return m.appendLoopSystem("No active loops."), nil
+	}
+	n := len(m.loops)
+	m.loops = nil
+	m.loopSeq++ // invalidate the pending poll tick
+	m.loopTicking = false
+	return m.appendLoopSystem(fmt.Sprintf("Stopped all %d loop(s).", n)), nil
+}
+
+// fireDueLoopIfIdle fires the earliest due loop when the session is idle. Called
+// from the poll tick; a no-op while a turn, modal, or queued user message is
+// pending (the loop simply waits for the next idle tick).
+func (m model) fireDueLoopIfIdle() (model, tea.Cmd) {
+	if m.loopBusy() || len(m.loops) == 0 {
+		return m, nil
+	}
+	now := m.now()
+	var due *loopState
+	for _, l := range m.loops {
+		if l.due(now) && (due == nil || l.nextRunAt.Before(due.nextRunAt)) {
+			due = l
+		}
+	}
+	if due == nil {
+		return m, nil
+	}
+	m.activeLoopID = due.id
+	due.nextRunAt = time.Time{} // mark running
+	return m.fireLoopPrompt(due.firePrompt())
+}
+
+// firePrompt is the text actually sent for this iteration. A self-paced plain
+// prompt is wrapped in the maintenance playbook so the model knows to do one
+// increment of work and end with a LOOP: control line; a /command or a
+// fixed-interval prompt is sent verbatim.
+func (l *loopState) firePrompt() string {
+	if l.mode == loopModeSelfPaced && !strings.HasPrefix(strings.TrimSpace(l.prompt), "/") {
+		return loopSelfPacePlaybook(l)
+	}
+	return l.prompt
+}
+
+// fireLoopPrompt runs a loop's prompt as a turn — a custom /command if it resolves
+// to one, otherwise a plain prompt.
+func (m model) fireLoopPrompt(prompt string) (model, tea.Cmd) {
+	if strings.HasPrefix(strings.TrimSpace(prompt), "/") {
+		if next, teaCmd, ok := m.handleUserCommand(prompt); ok {
+			return next, teaCmd
+		}
+	}
+	return m.launchPrompt(prompt)
+}
+
+// advanceLoop updates a loop after one of its iterations completes: it folds the
+// result into the failure/no-progress guards, honors a self-paced DONE/next-wake
+// control line, enforces the iteration and age caps, then schedules the next wake
+// (or stops the loop).
+func (m model) advanceLoop(id, finalAnswer string, runErr error) model {
+	l := m.findLoop(id)
+	if l == nil {
+		return m // stopped mid-run
+	}
+	l.iteration++
+	if runErr != nil {
+		l.failRun++
+	} else {
+		l.failRun = 0
+	}
+	res := strings.TrimSpace(finalAnswer)
+	if res != "" && res == l.lastResult {
+		l.repeatRun++
+	} else {
+		l.repeatRun = 0
+	}
+	l.lastResult = res
+
+	// Only self-paced iterations run the playbook, so only they can carry a control
+	// line; a failed turn has no trustworthy final answer to read one from.
+	done, wake := false, time.Duration(0)
+	if l.mode == loopModeSelfPaced && runErr == nil {
+		done, wake = parseLoopControl(finalAnswer)
+	}
+
+	switch {
+	case done:
+		return m.removeLoop(id, fmt.Sprintf("Loop %s finished — the task reported done after %d iteration(s).", id, l.iteration))
+	case l.failRun >= loopMaxFailures:
+		return m.removeLoop(id, fmt.Sprintf("Loop %s stopped after %d consecutive failed iterations.", id, l.failRun))
+	case l.iteration >= l.iterationCap():
+		return m.removeLoop(id, fmt.Sprintf("Loop %s stopped at its %d-iteration cap.", id, l.iteration))
+	case !l.createdAt.IsZero() && m.now().Sub(l.createdAt) >= loopMaxAge:
+		return m.removeLoop(id, fmt.Sprintf("Loop %s expired after %s.", id, formatLoopDuration(loopMaxAge)))
+	case l.repeatRun >= loopDoomThreshold:
+		return m.removeLoop(id, fmt.Sprintf("Loop %s stopped — %d identical results in a row (no progress).", id, l.repeatRun))
+	}
+
+	if l.mode == loopModeSelfPaced {
+		// A model-chosen next wake (from the control line) wins; otherwise fall back to
+		// an adaptive cadence that checks back often while work is fresh and settles to
+		// a slow heartbeat as iterations accrue.
+		delay := wake
+		if delay <= 0 {
+			delay = adaptiveSelfPaceDelay(l.iteration)
+		}
+		l.nextRunAt = m.now().Add(clampSelfPaceDelay(delay))
+	} else {
+		l.nextRunAt = m.now().Add(l.interval)
+	}
+	return m
+}
+
+// parseLoopControl reads a self-paced loop's control signal from the model's final
+// answer. The last control line wins (the model may reference the protocol before
+// emitting it). Returns done=true to stop the loop, or a next-wake hint (0 = none).
+func parseLoopControl(answer string) (done bool, wake time.Duration) {
+	// Normalize CRLF/CR so the line-end anchor can reach `$` (Go's (?m)$ sits right
+	// before `\n`, and the horizontal-whitespace class can't consume a stray `\r`).
+	norm := strings.ReplaceAll(answer, "\r\n", "\n")
+	norm = strings.ReplaceAll(norm, "\r", "\n")
+	matches := loopControlRe.FindAllStringSubmatch(norm, -1)
+	if len(matches) == 0 {
+		return false, 0
+	}
+	last := matches[len(matches)-1]
+	if strings.EqualFold(last[1], "done") {
+		return true, 0
+	}
+	if last[2] != "" {
+		if d, ok := parseLoopInterval(last[2]); ok {
+			return false, d
+		}
+	}
+	return false, 0
+}
+
+// loopSelfPacePlaybook wraps a self-paced loop's goal in the maintenance-loop
+// instructions the model follows each iteration: do one real increment of work,
+// then emit a single control line so the harness knows whether to stop or when to
+// wake next — the self-paced maintenance playbook the feature ships with.
+func loopSelfPacePlaybook(l *loopState) string {
+	var b strings.Builder
+	b.WriteString("You are running in a self-paced maintenance loop (iteration ")
+	b.WriteString(strconv.Itoa(l.iteration + 1))
+	b.WriteString("). Do one concrete increment of work toward the goal below — actual work, not just a plan — then stop and report.\n\n")
+	b.WriteString("Goal: ")
+	b.WriteString(strings.TrimSpace(l.prompt))
+	b.WriteString("\n\nEnd your reply with a control line — on its own line, starting with \"LOOP:\":\n")
+	b.WriteString("  LOOP: DONE          — the goal is fully met; the loop stops.\n")
+	b.WriteString("  LOOP: CONTINUE      — more to do; the loop wakes again automatically.\n")
+	b.WriteString("  LOOP: CONTINUE 10m  — more to do; wake after the delay you name (e.g. 5m, 1h).\n")
+	b.WriteString("A short note after the keyword is fine. Report DONE only when the goal is genuinely complete — the loop trusts that signal to stop.")
+	return b.String()
+}
+
+// adaptiveSelfPaceDelay picks a self-paced loop's next-wake by iteration: frequent
+// early (work is actively progressing), slowing to a heartbeat as it matures.
+func adaptiveSelfPaceDelay(iteration int) time.Duration {
+	switch {
+	case iteration < 2:
+		return 2 * time.Minute
+	case iteration < 5:
+		return 5 * time.Minute
+	case iteration < 10:
+		return 15 * time.Minute
+	default:
+		return 30 * time.Minute
+	}
+}
+
+func (m model) findLoop(id string) *loopState {
+	for _, l := range m.loops {
+		if l.id == id {
+			return l
+		}
+	}
+	return nil
+}
+
+func (m model) removeLoop(id, note string) model {
+	kept := make([]*loopState, 0, len(m.loops))
+	for _, l := range m.loops {
+		if l.id != id {
+			kept = append(kept, l)
+		}
+	}
+	m.loops = kept
+	m.loopSeq++ // invalidate the pending poll tick; a fresh one is scheduled if loops remain
+	m.loopTicking = false
+	if note != "" {
+		m = m.appendLoopSystem(note)
+	}
+	return m
+}
+
+// ensureLoopTick starts the idle poll ticker if it is not already running.
+func (m model) ensureLoopTick() (model, tea.Cmd) {
+	if m.loopTicking || len(m.loops) == 0 {
+		return m, nil
+	}
+	m.loopTicking = true
+	return m, m.scheduleLoopTick()
+}
+
+func (m model) scheduleLoopTick() tea.Cmd {
+	seq := m.loopSeq
+	return tea.Tick(loopPollInterval, func(time.Time) tea.Msg {
+		return loopTickMsg{seq: seq}
+	})
+}
+
+// loopBusy reports whether the session is too busy for a loop to fire — a turn,
+// queued user message, compaction, or ANY blocking modal (permission/askUser/spec
+// review, provider or MCP wizard, MCP manager, or an open picker) is in flight.
+// The modal check is load-bearing: a loop must not launch a run behind an open
+// /resume picker, or that run would complete into whatever session the user then
+// switches to. Mirrors launchQueuedMessageIfReady so loops and queued prompts never
+// collide.
+func (m model) loopBusy() bool {
+	return m.pending || m.exiting || m.compactInFlight || m.hasQueuedMessage() || !m.noBlockingModal()
+}
+
+func (m model) appendLoopSystem(text string) model {
+	m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: text})
+	return m
+}
+
+// loopActive reports whether any loop is running (for the footer + leave warning).
+func (m model) loopActive() bool { return len(m.loops) > 0 }
+
+// loopFooterSummary renders the persistent "N loops · next 3:05pm" footer segment,
+// or "" when no loops are active.
+func (m model) loopFooterSummary() string {
+	if len(m.loops) == 0 {
+		return ""
+	}
+	var next time.Time
+	for _, l := range m.loops {
+		if l.nextRunAt.IsZero() || l.paused {
+			continue
+		}
+		if next.IsZero() || l.nextRunAt.Before(next) {
+			next = l.nextRunAt
+		}
+	}
+	label := fmt.Sprintf("%d loop", len(m.loops))
+	if len(m.loops) != 1 {
+		label += "s"
+	}
+	if next.IsZero() {
+		return label
+	}
+	return label + " · next " + next.Format("3:04pm")
+}
+
+func (m model) loopListText() string {
+	if len(m.loops) == 0 {
+		return "No active loops."
+	}
+	var b strings.Builder
+	b.WriteString("Active loops:\n")
+	now := m.now()
+	for _, l := range m.loops {
+		when := "running"
+		if !l.nextRunAt.IsZero() {
+			if d := l.nextRunAt.Sub(now); d > 0 {
+				when = "next in " + formatLoopDuration(d.Round(time.Second))
+			} else {
+				when = "due"
+			}
+		}
+		b.WriteString(fmt.Sprintf("  %s · %s · iter %d · %s · %s\n",
+			l.id, l.cadenceText(), l.iteration, when, truncateLoopPrompt(l.prompt)))
+	}
+	b.WriteString("Stop with /loop stop <id> or /loop stop all.")
+	return b.String()
+}
+
+func loopUsageText() string {
+	return "Repeat a prompt or command:\n" +
+		"  /loop 5m /babysit-prs   — run a command every 5 minutes\n" +
+		"  /loop watch CI every 2m — trailing interval form\n" +
+		"  /loop keep tidying docs — self-paced (the model picks its own cadence and stops when done)\n" +
+		"  /loop list              — show active loops\n" +
+		"  /loop stop [id|all]     — stop a loop\n" +
+		"Loops run while this session is idle and stop when you close it."
+}
+
+// validateLoopTarget rejects looping a built-in command or an unresolved custom
+// command — only a prompt or an existing custom /command (.zero/commands/<name>.md)
+// may loop. Resolving custom commands up front stops a typo'd `/loop 5m /nope` from
+// being scheduled and then re-sent as literal text on every tick.
+func (m model) validateLoopTarget(prompt string) (string, bool) {
+	p := strings.TrimSpace(prompt)
+	if p == "" {
+		return "Nothing to loop — give a prompt or a /command.", false
+	}
+	if strings.HasPrefix(p, "/") {
+		switch parseCommand(p).kind {
+		case commandPrompt:
+			// A bare "/" or similar that isn't a command — treat as a plain prompt.
+		case commandUnknown:
+			name, _ := splitUserCommand(p)
+			if _, ok := m.lookupUserCommand(name); !ok {
+				return "No command /" + name + " — a loop can only run a prompt or an existing custom /command.", false
+			}
+		default:
+			return "A loop can only run a prompt or a custom /command, not a built-in like " + strings.Fields(p)[0] + ".", false
+		}
+	}
+	return "", true
+}
+
+// clearLoopsForSessionSwitch drops every active loop and its ticker. Loops belong to
+// the session that created them; carrying them across /new or /resume would fire the
+// old session's prompt into an unrelated conversation. Returns the count cleared so
+// the caller can note it. Pure state reset — no transcript writes.
+func (m model) clearLoopsForSessionSwitch() (model, int) {
+	n := len(m.loops)
+	if n == 0 {
+		return m, 0
+	}
+	m.loops = nil
+	m.activeLoopID = ""
+	m.loopTicking = false
+	m.loopSeq++ // invalidate any pending poll tick
+	return m, n
+}
+
+func truncateLoopPrompt(prompt string) string {
+	const max = 48
+	p := strings.TrimSpace(strings.ReplaceAll(prompt, "\n", " "))
+	runes := []rune(p)
+	if len(runes) <= max {
+		return p
+	}
+	return strings.TrimSpace(string(runes[:max])) + "…"
+}
+
+// clampSelfPaceDelay bounds a model-chosen self-paced delay to the self-pace
+// band, defaulting an unset/invalid value.
+func clampSelfPaceDelay(d time.Duration) time.Duration {
+	switch {
+	case d <= 0:
+		return loopSelfPaceDefault
+	case d < loopSelfPaceMin:
+		return loopSelfPaceMin
+	case d > loopSelfPaceMax:
+		return loopSelfPaceMax
+	default:
+		return d
+	}
+}
+
+// formatLoopDuration renders a duration compactly (90s, 5m, 2h, 1d) for status
+// text, preferring the largest whole unit.
+func formatLoopDuration(d time.Duration) string {
+	switch {
+	case d%(24*time.Hour) == 0 && d >= 24*time.Hour:
+		return strconv.Itoa(int(d/(24*time.Hour))) + "d"
+	case d%time.Hour == 0 && d >= time.Hour:
+		return strconv.Itoa(int(d/time.Hour)) + "h"
+	case d%time.Minute == 0 && d >= time.Minute:
+		return strconv.Itoa(int(d/time.Minute)) + "m"
+	default:
+		return strconv.Itoa(int(d/time.Second)) + "s"
+	}
+}

internal/tui/loop_controller_test.go

@@ -0,0 +1,460 @@
+package tui
+
+import (
+	"context"
+	"errors"
+	"strings"
+	"testing"
+	"time"
+
+	tea "charm.land/bubbletea/v2"
+
+	"github.com/Gitlawb/zero/internal/usercommands"
+)
+
+func loopTestModel(t *testing.T, now time.Time) model {
+	t.Helper()
+	m := newModel(context.Background(), Options{})
+	m.now = func() time.Time { return now }
+	return m
+}
+
+func startFixedLoop(m model, prompt string, interval time.Duration) model {
+	m, _ = m.startLoop(loopCommand{action: loopActionStart, mode: loopModeFixed, prompt: prompt, interval: interval})
+	return m
+}
+
+func TestStartLoopRegistersAndSchedules(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "check the build", 5*time.Minute)
+
+	if len(m.loops) != 1 {
+		t.Fatalf("want 1 loop, got %d", len(m.loops))
+	}
+	l := m.loops[0]
+	if l.mode != loopModeFixed || l.interval != 5*time.Minute || l.prompt != "check the build" {
+		t.Fatalf("unexpected loop %+v", l)
+	}
+	// First iteration is due immediately (nextRunAt == now).
+	if !l.due(now) {
+		t.Errorf("first iteration should be due at creation")
+	}
+	if !m.loopTicking {
+		t.Errorf("starting a loop should start the poll ticker")
+	}
+}
+
+func TestAdvanceLoopSchedulesNextWake(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "poll", 5*time.Minute)
+	id := m.loops[0].id
+
+	m = m.advanceLoop(id, "did some work", nil)
+	l := m.loops[0]
+	if l.iteration != 1 {
+		t.Fatalf("iteration = %d, want 1", l.iteration)
+	}
+	if !l.nextRunAt.Equal(now.Add(5 * time.Minute)) {
+		t.Fatalf("nextRunAt = %v, want +5m", l.nextRunAt)
+	}
+}
+
+func TestSelfPacedUsesModelDelay(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m, _ = m.startLoop(loopCommand{action: loopActionStart, mode: loopModeSelfPaced, prompt: "keep tidying"})
+	id := m.loops[0].id
+	// The model carries its chosen next wake in the reply's control line.
+	m = m.advanceLoop(id, "made progress\nLOOP: CONTINUE 10m", nil)
+	if len(m.loops) == 0 {
+		t.Fatal("a CONTINUE control line should keep the loop running")
+	}
+	if !m.loops[0].nextRunAt.Equal(now.Add(10 * time.Minute)) {
+		t.Fatalf("self-paced nextRunAt = %v, want +10m", m.loops[0].nextRunAt)
+	}
+}
+
+func TestLoopDoneStops(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m, _ = m.startLoop(loopCommand{action: loopActionStart, mode: loopModeSelfPaced, prompt: "finish the task"})
+	id := m.loops[0].id
+	m = m.advanceLoop(id, "all done\nLOOP: DONE", nil)
+	if len(m.loops) != 0 {
+		t.Fatalf("loop should stop when the task reports done, %d remain", len(m.loops))
+	}
+}
+
+func TestFixedLoopIgnoresControlLine(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "watch CI", time.Minute)
+	id := m.loops[0].id
+	// A fixed-interval loop never runs the playbook, so a stray control line in the
+	// output is not a completion signal — it keeps its wall-clock cadence.
+	m = m.advanceLoop(id, "LOOP: DONE", nil)
+	if len(m.loops) != 1 {
+		t.Fatal("a fixed-interval loop should ignore a control line and keep running")
+	}
+	if !m.loops[0].nextRunAt.Equal(now.Add(time.Minute)) {
+		t.Fatalf("fixed nextRunAt = %v, want +1m", m.loops[0].nextRunAt)
+	}
+}
+
+func TestLoopExpiresByAge(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "forgotten", time.Minute)
+	id := m.loops[0].id
+	m.loops[0].createdAt = now.Add(-loopMaxAge - time.Hour) // created past the age cap
+	m = m.advanceLoop(id, "still going", nil)
+	if len(m.loops) != 0 {
+		t.Fatal("a loop past its age cap should auto-expire")
+	}
+}
+
+func TestLoopDoomGuardStops(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "spin", time.Minute)
+	id := m.loops[0].id
+	for i := 0; i < loopDoomThreshold+1 && len(m.loops) > 0; i++ {
+		m = m.advanceLoop(id, "identical answer", nil)
+	}
+	if len(m.loops) != 0 {
+		t.Fatalf("doom guard should stop a loop repeating identical results")
+	}
+}
+
+func TestLoopIterationCapStops(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "bounded", time.Minute)
+	m.loops[0].maxIter = 3
+	id := m.loops[0].id
+	for i := 0; i < 3 && len(m.loops) > 0; i++ {
+		m = m.advanceLoop(id, "answer "+string(rune('a'+i)), nil) // distinct answers so doom doesn't fire
+	}
+	if len(m.loops) != 0 {
+		t.Fatalf("loop should stop at its iteration cap")
+	}
+}
+
+func TestStopLoopByID(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "a", time.Minute)
+	m = startFixedLoop(m, "b", time.Minute)
+	id := m.loops[0].id
+	m, cmd := m.stopLoop(id)
+	if len(m.loops) != 1 || m.findLoop(id) != nil {
+		t.Fatalf("stopLoop(%s) should remove exactly that loop", id)
+	}
+	// Stopping one of several loops must keep the poll ticker alive for the rest:
+	// removeLoop kills the ticker, so stopLoop has to re-arm it (jatmn).
+	if cmd == nil || !m.loopTicking {
+		t.Fatal("stopping one of several loops must leave the remaining loop scheduled (ticker re-armed)")
+	}
+	// Bare stop with a single active loop stops that sole loop (parseLoopCommand
+	// leaves the target empty and stopLoop special-cases the one-loop case).
+	soleID := m.loops[0].id
+	m, _ = m.stopLoop("")
+	if len(m.loops) != 0 || m.findLoop(soleID) != nil {
+		t.Fatalf("bare stop should remove the sole active loop")
+	}
+	m = startFixedLoop(m, "c", time.Minute)
+	m = startFixedLoop(m, "d", time.Minute)
+	m, _ = m.stopAllLoops()
+	if len(m.loops) != 0 {
+		t.Fatalf("stopAllLoops should clear all loops")
+	}
+}
+
+func TestFireDueLoopSkipsWhenBusy(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", time.Minute)
+	m.pending = true // a turn is in flight
+	got, cmd := m.fireDueLoopIfIdle()
+	if got.activeLoopID != "" || cmd != nil {
+		t.Fatalf("a due loop must not fire while a turn is pending")
+	}
+}
+
+func TestFireDueLoopSkipsBehindModal(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "poll", time.Minute) // due immediately
+	m.picker = &commandPicker{}                // e.g. an open /resume session picker
+	got, cmd := m.fireDueLoopIfIdle()
+	if got.activeLoopID != "" || cmd != nil {
+		t.Fatal("a due loop must not launch a run behind an open picker/modal — it would complete into whatever session the user switches to")
+	}
+	if got.loops[0].nextRunAt.IsZero() {
+		t.Fatal("a loop skipped because a modal is open must stay scheduled, not have its next run cleared")
+	}
+}
+
+func TestAdaptiveSelfPaceDelayWidensOverTime(t *testing.T) {
+	if adaptiveSelfPaceDelay(0) >= adaptiveSelfPaceDelay(5) {
+		t.Error("early iterations should check back sooner than later ones")
+	}
+	if adaptiveSelfPaceDelay(20) != 30*time.Minute {
+		t.Errorf("a mature loop should settle to a 30m heartbeat, got %v", adaptiveSelfPaceDelay(20))
+	}
+}
+
+func TestLoopFooterSummary(t *testing.T) {
+	now := time.Date(2026, 7, 5, 15, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	if m.loopFooterSummary() != "" {
+		t.Error("no loops -> empty footer summary")
+	}
+	m = startFixedLoop(m, "a", 5*time.Minute)
+	m.loops[0].nextRunAt = now.Add(5 * time.Minute)
+	got := m.loopFooterSummary()
+	wantWake := "next " + now.Add(5*time.Minute).Format("3:04pm")
+	if !strings.HasPrefix(got, "1 loop") || !strings.Contains(got, wantWake) {
+		t.Fatalf("footer summary = %q, want it to start with a loop count and contain %q", got, wantWake)
+	}
+}
+
+func TestLoopCommandThroughSubmit(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m.input.SetValue("/loop 5m tidy the imports")
+	updated, _ := m.Update(testKey(tea.KeyEnter))
+	next := updated.(model)
+	if len(next.loops) != 1 {
+		t.Fatalf("submitting /loop should create a loop, got %d", len(next.loops))
+	}
+	if next.loops[0].mode != loopModeFixed || next.loops[0].interval != 5*time.Minute {
+		t.Fatalf("unexpected loop from submit: %+v", next.loops[0])
+	}
+	if !next.loopTicking {
+		t.Fatalf("submitting /loop should start the poll ticker")
+	}
+
+	// /loop stop all through the same path clears it.
+	next.input.SetValue("/loop stop all")
+	updated2, _ := next.Update(testKey(tea.KeyEnter))
+	final := updated2.(model)
+	if len(final.loops) != 0 {
+		t.Fatalf("/loop stop all should clear loops, got %d", len(final.loops))
+	}
+}
+
+func TestStaleLoopTickIgnored(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", time.Minute)
+	m.loopSeq = 7
+	// A tick from before the seq changed must be dropped and stop the ticker.
+	updated, cmd := m.Update(loopTickMsg{seq: 3})
+	next := updated.(model)
+	if next.loopTicking {
+		t.Error("a stale loop tick should stop the ticker")
+	}
+	if cmd != nil {
+		t.Error("a stale loop tick should not reschedule")
+	}
+}
+
+func TestLoopStopsAfterConsecutiveFailures(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "flaky", time.Minute)
+	id := m.loops[0].id
+	boom := errors.New("boom")
+	for i := 0; i < loopMaxFailures && len(m.loops) > 0; i++ {
+		m = m.advanceLoop(id, "", boom)
+	}
+	if len(m.loops) != 0 {
+		t.Fatalf("loop should stop after %d consecutive failed iterations", loopMaxFailures)
+	}
+}
+
+func TestLoopFailureCounterResetsOnSuccess(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "recovers", time.Minute)
+	id := m.loops[0].id
+	m = m.advanceLoop(id, "", errors.New("x"))
+	m = m.advanceLoop(id, "", errors.New("x"))
+	m = m.advanceLoop(id, "back to healthy", nil) // a success resets the streak
+	if len(m.loops) != 1 {
+		t.Fatalf("a recovered failure streak should not stop the loop")
+	}
+	if m.loops[0].failRun != 0 {
+		t.Fatalf("a successful iteration should reset failRun, got %d", m.loops[0].failRun)
+	}
+}
+
+func TestCancelRunClearsActiveLoopAndRearms(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", 5*time.Minute)
+	m.activeLoopID = m.loops[0].id
+	m.loops[0].nextRunAt = time.Time{} // as if the iteration is running
+	m.pending = true
+	m.activeRunID = 7
+	m.runCancel = func() {}
+
+	m.cancelRun()
+
+	if m.activeLoopID != "" {
+		t.Fatal("cancel should clear the active-loop tag so the next turn isn't misattributed")
+	}
+	if m.loops[0].nextRunAt.IsZero() {
+		t.Fatal("cancel should re-arm the interrupted loop, not leave it running forever")
+	}
+	if !m.loops[0].nextRunAt.Equal(now.Add(5 * time.Minute)) {
+		t.Fatalf("re-armed nextRunAt = %v, want +5m", m.loops[0].nextRunAt)
+	}
+}
+
+func TestValidateLoopTargetRejectsBuiltin(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	if _, ok := m.validateLoopTarget("/model list"); ok {
+		t.Error("looping a built-in command should be rejected")
+	}
+	if _, ok := m.validateLoopTarget("keep improving docs"); !ok {
+		t.Error("a plain prompt should be a valid loop target")
+	}
+	if _, ok := m.validateLoopTarget(""); ok {
+		t.Error("an empty target should be rejected")
+	}
+	// A custom command that does not exist is rejected up front, so it is never
+	// scheduled and then re-sent as literal "/…" text on every tick.
+	if _, ok := m.validateLoopTarget("/babysit-prs"); ok {
+		t.Error("an unresolved custom command should be rejected")
+	}
+	// A registered custom command is accepted.
+	m.userCommands = []usercommands.Command{{Name: "babysit-prs", Template: "check the PRs"}}
+	if _, ok := m.validateLoopTarget("/babysit-prs"); !ok {
+		t.Error("an existing custom command should be a valid loop target")
+	}
+}
+
+func TestSelfPacedCommandLoopRejected(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m.userCommands = []usercommands.Command{{Name: "babysit-prs", Template: "check the PRs"}}
+	// A /command with no interval parses as self-paced, but self-paced mode drives
+	// a free-form goal via the playbook + LOOP: protocol, which a command's
+	// expanded template never carries — so a bare self-paced /command is rejected.
+	m, _ = m.startLoop(loopCommand{action: loopActionStart, mode: loopModeSelfPaced, prompt: "/babysit-prs"})
+	if len(m.loops) != 0 {
+		t.Fatal("a bare self-paced /command loop should be rejected (a command loop needs an interval)")
+	}
+	// The same command with an interval (fixed) is accepted.
+	m, _ = m.startLoop(loopCommand{action: loopActionStart, mode: loopModeFixed, prompt: "/babysit-prs", interval: 5 * time.Minute})
+	if len(m.loops) != 1 {
+		t.Fatal("a fixed-interval /command loop should be accepted")
+	}
+}
+
+func TestClearLoopsForSessionSwitch(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "a", time.Minute)
+	m = startFixedLoop(m, "b", time.Minute)
+	m.activeLoopID = m.loops[0].id
+	m, n := m.clearLoopsForSessionSwitch()
+	if n != 2 || len(m.loops) != 0 || m.activeLoopID != "" || m.loopTicking {
+		t.Fatalf("session switch should clear all loop state; got n=%d loops=%d active=%q ticking=%v",
+			n, len(m.loops), m.activeLoopID, m.loopTicking)
+	}
+}
+
+func TestStartNewSessionStopsLoops(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", time.Minute)
+	m = m.startNewSession()
+	if len(m.loops) != 0 || m.loopTicking {
+		t.Fatal("/new should stop loops tied to the previous session")
+	}
+}
+
+func TestLoopClearRequiresConfirm(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", time.Minute)
+
+	// First /clear with a loop active arms the confirm and does not clear yet.
+	m.input.SetValue("/clear")
+	u1, _ := m.Update(testKey(tea.KeyEnter))
+	n1 := u1.(model)
+	if n1.loopLeavePrompt != commandClear {
+		t.Fatal("first /clear with active loops should arm the confirm, not clear")
+	}
+	if len(n1.loops) != 1 {
+		t.Fatal("the loop should still be active after the warning")
+	}
+
+	// A different command disarms the confirm.
+	n1.input.SetValue("/loop list")
+	u2, _ := n1.Update(testKey(tea.KeyEnter))
+	n2 := u2.(model)
+	if n2.loopLeavePrompt != commandEmpty {
+		t.Fatal("an intervening command should disarm the leave confirm")
+	}
+
+	// Re-arm, then a second consecutive /clear confirms (disarms + clears).
+	n2.input.SetValue("/clear")
+	u3, _ := n2.Update(testKey(tea.KeyEnter))
+	n3 := u3.(model)
+	n3.input.SetValue("/clear")
+	u4, _ := n3.Update(testKey(tea.KeyEnter))
+	n4 := u4.(model)
+	if n4.loopLeavePrompt != commandEmpty {
+		t.Fatal("a second consecutive /clear should confirm and disarm")
+	}
+	if len(n4.loops) != 1 {
+		t.Fatal("/clear keeps loops running (it wipes the screen, not the session)")
+	}
+	// The confirmed clear must actually wipe the transcript, not silently no-op:
+	// only the clear path appends the "Transcript cleared" note, and the pre-clear
+	// loop-start row must be gone.
+	clearedNote, staleRow := false, false
+	for _, r := range n4.transcript {
+		if strings.Contains(r.text, "Transcript cleared") {
+			clearedNote = true
+		}
+		if strings.Contains(r.text, "Loop L1 started") {
+			staleRow = true
+		}
+	}
+	if !clearedNote || staleRow {
+		t.Fatalf("the second /clear must wipe the transcript (clearedNote=%v staleRow=%v)", clearedNote, staleRow)
+	}
+}
+
+func TestLeaveConfirmDisarmedByQueuedPrompt(t *testing.T) {
+	now := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	m := loopTestModel(t, now)
+	m = startFixedLoop(m, "x", time.Minute)
+
+	// Arm the /clear confirm.
+	m.input.SetValue("/clear")
+	u1, _ := m.Update(testKey(tea.KeyEnter))
+	n1 := u1.(model)
+	if n1.loopLeavePrompt != commandClear {
+		t.Fatal("first /clear should arm the confirm")
+	}
+
+	// A prompt submitted while a run streams is queued via an early return in
+	// handleSubmit; it must still disarm the confirm (the disarm runs before those
+	// returns). Otherwise a later /clear would be treated as the second press.
+	n1.pending = true
+	n1.input.SetValue("a follow-up question")
+	u2, _ := n1.Update(testKey(tea.KeyEnter))
+	n2 := u2.(model)
+	if n2.loopLeavePrompt != commandEmpty {
+		t.Fatal("a queued prompt should disarm the leave confirm; the early return must not skip the disarm")
+	}
+}

internal/tui/loop_test.go

@@ -0,0 +1,156 @@
+package tui
+
+import (
+	"strings"
+	"testing"
+	"time"
+)
+
+func TestParseLoopCommandModes(t *testing.T) {
+	cases := []struct {
+		in       string
+		action   loopAction
+		mode     loopMode
+		prompt   string
+		interval time.Duration
+	}{
+		{"", loopActionUsage, 0, "", 0},
+		{"list", loopActionList, 0, "", 0},
+		{"status", loopActionList, 0, "", 0},
+		{"stop all", loopActionStopAll, 0, "", 0},
+		{"stop ab12", loopActionStop, 0, "", 0},
+		{"5m /babysit-prs", loopActionStart, loopModeFixed, "/babysit-prs", 5 * time.Minute},
+		{"90s check the build", loopActionStart, loopModeFixed, "check the build", 90 * time.Second},
+		{"watch CI every 2m", loopActionStart, loopModeFixed, "watch CI", 2 * time.Minute},
+		{"keep improving the docs", loopActionStart, loopModeSelfPaced, "keep improving the docs", 0},
+		// "every PR" is not a cadence — the token after "every" isn't a duration.
+		{"review every PR", loopActionStart, loopModeSelfPaced, "review every PR", 0},
+	}
+	for _, c := range cases {
+		got := parseLoopCommand(c.in)
+		if got.action != c.action {
+			t.Errorf("%q action = %v, want %v", c.in, got.action, c.action)
+		}
+		if c.action == loopActionStart {
+			if got.mode != c.mode {
+				t.Errorf("%q mode = %v, want %v", c.in, got.mode, c.mode)
+			}
+			if got.prompt != c.prompt {
+				t.Errorf("%q prompt = %q, want %q", c.in, got.prompt, c.prompt)
+			}
+			if got.interval != c.interval {
+				t.Errorf("%q interval = %v, want %v", c.in, got.interval, c.interval)
+			}
+		}
+	}
+}
+
+func TestParseLoopCommandStopTarget(t *testing.T) {
+	if got := parseLoopCommand("stop"); got.action != loopActionStop || got.targetID != "" {
+		t.Fatalf("bare stop = %+v, want stop with empty target", got)
+	}
+	if got := parseLoopCommand("stop XyZ9"); got.targetID != "XyZ9" {
+		t.Fatalf("stop target = %q, want XyZ9", got.targetID)
+	}
+}
+
+func TestClampLoopInterval(t *testing.T) {
+	if d, note := clampLoopInterval(5 * time.Second); d != loopMinInterval || note == "" {
+		t.Fatalf("below-min = (%v,%q), want raised to min with note", d, note)
+	}
+	if d, note := clampLoopInterval(48 * time.Hour); d != loopMaxInterval || note == "" {
+		t.Fatalf("above-max = (%v,%q), want lowered to max with note", d, note)
+	}
+	if d, note := clampLoopInterval(5 * time.Minute); d != 5*time.Minute || note != "" {
+		t.Fatalf("in-range = (%v,%q), want unchanged, no note", d, note)
+	}
+}
+
+func TestClampSelfPaceDelay(t *testing.T) {
+	if got := clampSelfPaceDelay(0); got != loopSelfPaceDefault {
+		t.Errorf("zero delay = %v, want default %v", got, loopSelfPaceDefault)
+	}
+	if got := clampSelfPaceDelay(10 * time.Second); got != loopSelfPaceMin {
+		t.Errorf("below-min = %v, want %v", got, loopSelfPaceMin)
+	}
+	if got := clampSelfPaceDelay(3 * time.Hour); got != loopSelfPaceMax {
+		t.Errorf("above-max = %v, want %v", got, loopSelfPaceMax)
+	}
+	if got := clampSelfPaceDelay(10 * time.Minute); got != 10*time.Minute {
+		t.Errorf("in-band = %v, want unchanged", got)
+	}
+}
+
+func TestFormatLoopDuration(t *testing.T) {
+	cases := map[time.Duration]string{
+		30 * time.Second: "30s",
+		90 * time.Second: "90s",
+		5 * time.Minute:  "5m",
+		2 * time.Hour:    "2h",
+		24 * time.Hour:   "1d",
+	}
+	for d, want := range cases {
+		if got := formatLoopDuration(d); got != want {
+			t.Errorf("formatLoopDuration(%v) = %q, want %q", d, got, want)
+		}
+	}
+}
+
+func TestParseLoopControl(t *testing.T) {
+	cases := []struct {
+		in   string
+		done bool
+		wake time.Duration
+	}{
+		{"did the work\nLOOP: DONE", true, 0},
+		{"progress\nLOOP: CONTINUE", false, 0},
+		{"progress\nLOOP: CONTINUE 10m", false, 10 * time.Minute},
+		{"progress\n- loop: continue 1h", false, time.Hour},                     // markdown bullet, lowercase
+		{"LOOP: CONTINUE 5m\n...more...\nLOOP: DONE", true, 0},                  // last control line wins
+		{"no control line here", false, 0},                                      // absent -> adaptive
+		{"LOOP: DONE — all tests pass", true, 0},                                // a trailing note is fine
+		{"progress\nLOOP: CONTINUE 5m — still tidying", false, 5 * time.Minute}, // note after the interval
+		{"work done.\r\nLOOP: DONE\r\n", true, 0},                               // CRLF endings still parse
+		{"work\r\nLOOP: CONTINUE 10m\r\n", false, 10 * time.Minute},             // CRLF + interval
+		{"I will emit LOOP: DONE when finished", false, 0},                      // mid-sentence mention doesn't match
+		{"LOOP: CONTINUE 99z", false, 0},                                        // bad unit -> continue, no wake hint
+	}
+	for _, c := range cases {
+		done, wake := parseLoopControl(c.in)
+		if done != c.done || wake != c.wake {
+			t.Errorf("parseLoopControl(%q) = (%v,%v), want (%v,%v)", c.in, done, wake, c.done, c.wake)
+		}
+	}
+}
+
+func TestFirePromptWrapsSelfPacedOnly(t *testing.T) {
+	self := &loopState{mode: loopModeSelfPaced, prompt: "tidy the docs"}
+	got := self.firePrompt()
+	if !strings.Contains(got, "LOOP: DONE") || !strings.Contains(got, "tidy the docs") {
+		t.Errorf("self-paced firePrompt should embed the playbook and goal, got %q", got)
+	}
+	fixed := &loopState{mode: loopModeFixed, prompt: "check the build"}
+	if fixed.firePrompt() != "check the build" {
+		t.Errorf("fixed-interval firePrompt should be verbatim, got %q", fixed.firePrompt())
+	}
+	// A self-paced /command is a real command, not a goal — send it verbatim, no playbook.
+	cmd := &loopState{mode: loopModeSelfPaced, prompt: "/babysit"}
+	if cmd.firePrompt() != "/babysit" {
+		t.Errorf("self-paced /command firePrompt should be verbatim, got %q", cmd.firePrompt())
+	}
+}
+
+func TestLoopStateDue(t *testing.T) {
+	base := time.Date(2026, 7, 5, 12, 0, 0, 0, time.UTC)
+	l := &loopState{nextRunAt: base}
+	if l.due(base.Add(-time.Second)) {
+		t.Error("loop should not be due before nextRunAt")
+	}
+	if !l.due(base) {
+		t.Error("loop should be due at nextRunAt")
+	}
+	l.paused = true
+	if l.due(base.Add(time.Hour)) {
+		t.Error("paused loop should never be due")
+	}
+}

internal/tui/model.go

@@ -29,6 +29,7 @@ import (
 	"github.com/Gitlawb/zero/internal/providers/providerio"
 	"github.com/Gitlawb/zero/internal/sandbox"
 	"github.com/Gitlawb/zero/internal/sessions"
+	"github.com/Gitlawb/zero/internal/skills"
 	"github.com/Gitlawb/zero/internal/streamjson"
 	"github.com/Gitlawb/zero/internal/tools"
 	"github.com/Gitlawb/zero/internal/usage"
@@ -62,6 +63,7 @@ type model struct {
 	ctx                         context.Context
 	cwd                         string
 	userCommands                []usercommands.Command // file-sourced /commands (.zero/commands)
+	loadSkills                  func() []skills.Skill  // lazy installed-skills loader for /skills + /<skill-name>
 	userConfigPath              string
 	doctorUserConfigPath        string
 	projectConfigPath           string
@@ -188,10 +190,22 @@ type model struct {
 	// like a frozen terminal (for ANY provider, not just slow ones). Zero = idle.
 	turnStartedAt time.Time
 	queuedMessage string
-	exiting       bool
-	runCancel     context.CancelFunc
-	runID         int
-	activeRunID   int
+	// loops holds the session's active /loop definitions (see loop.go). activeLoopID
+	// tags the in-flight run when it is a loop iteration (empty = a user turn), so the
+	// completion seam knows whether to advance a loop. loopSeq invalidates a stale
+	// pending poll tick when loops are stopped; loopTicking guards against scheduling
+	// a second poll ticker. loopLeavePrompt arms a one-shot confirm before /clear or
+	// /quit while loops are active (see handleSubmit).
+	loops           []*loopState
+	activeLoopID    string
+	loopSeq         int
+	loopCounter     int
+	loopTicking     bool
+	loopLeavePrompt commandKind
+	exiting         bool
+	runCancel       context.CancelFunc
+	runID           int
+	activeRunID     int
 	// flushRunIDs holds the ids of runs cancelled while still in flight, mapped
 	// to the session they were recording into AT CANCEL TIME. Each cancelled
 	// agent goroutine keeps running to completion and returns its accumulated
@@ -735,6 +749,7 @@ func newModel(ctx context.Context, options Options) model {
 		cwd:                         cwd,
 		swarmDoneAt:                 map[string]time.Time{},
 		userCommands:                loadedUserCommands,
+		loadSkills:                  options.LoadSkills,
 		composerCursorVisible:       true,
 		userConfigPath:              options.UserConfigPath,
 		doctorUserConfigPath:        doctorUserConfigPath,
@@ -1893,6 +1908,16 @@ func (m model) updateModel(msg tea.Msg) (tea.Model, tea.Cmd) {
 		m.clearComposer()
 		m.clearSuggestions()
 		return m, nil
+	case loopTickMsg:
+		// Idle poll for due loops. A stale tick (loops changed) or an empty loop set
+		// ends the ticker; otherwise fire the earliest due loop if idle and reschedule.
+		if msg.seq != m.loopSeq || len(m.loops) == 0 {
+			m.loopTicking = false
+			return m, nil
+		}
+		var fireCmd tea.Cmd
+		m, fireCmd = m.fireDueLoopIfIdle()
+		return m, tea.Batch(fireCmd, m.scheduleLoopTick())
 	case agentResponseMsg:
 		if msg.runID != m.activeRunID {
 			// A run cancelled while in flight still finishes in its goroutine and
@@ -2062,8 +2087,25 @@ func (m model) updateModel(msg tea.Msg) (tea.Model, tea.Cmd) {
 		// complete once the turn settles.
 		var sweepCmd tea.Cmd
 		m, sweepCmd = m.maybeGitSweep()
+		// If this run was a loop iteration, advance that loop (schedule its next wake
+		// or stop it). Done before launchQueuedMessageIfReady so a user's queued prompt
+		// still wins the immediate re-launch; the loop fires on the next idle tick.
+		var loopTickCmd tea.Cmd
+		if loopID := m.activeLoopID; loopID != "" {
+			m.activeLoopID = ""
+			loopFinalAnswer := ""
+			for _, row := range msg.rows {
+				if row.kind == rowAssistant && row.final {
+					loopFinalAnswer = row.text
+				}
+			}
+			m = m.advanceLoop(loopID, loopFinalAnswer, msg.err)
+			// advanceLoop -> removeLoop may have stopped the ticker; restart it if
+			// other loops remain.
+			m, loopTickCmd = m.ensureLoopTick()
+		}
 		next, queuedCmd := m.launchQueuedMessageIfReady()
-		return next, tea.Batch(titleCmd, recapCmd, sweepCmd, queuedCmd)
+		return next, tea.Batch(titleCmd, recapCmd, sweepCmd, queuedCmd, loopTickCmd)
 	case sessionTitleGeneratedMsg:
 		return m.handleSessionTitleGenerated(msg)
 	case recapGeneratedMsg:
@@ -3730,6 +3772,11 @@ func (m model) choosePicker() (tea.Model, tea.Cmd) {
 		if text != "" {
 			m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: text})
 		}
+	case pickerSkill:
+		// Fill the composer with "/name " so the user adds their request before
+		// submitting (a bare second Enter runs it without one); names the slash
+		// path cannot reach run immediately instead.
+		m, cmd = m.chooseSkillFromPicker(item)
 	case pickerTheme:
 		// The hovered palette is already live from the preview; handleThemeCommand
 		// records the choice (m.themeMode) and re-applies it, and reports the switch.
@@ -3781,6 +3828,13 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 		return m, nil
 	}
 	command := parseCommand(input)
+	// A pending /clear or /quit leave-confirmation is armed for the immediately-next
+	// repeat of that same command only; any other submission — including one queued
+	// or deferred by the early returns below — disarms it. Runs before those returns
+	// so an interposed prompt can't be skipped over and leave the gate falsely armed.
+	if m.loopLeavePrompt != commandEmpty && command.kind != m.loopLeavePrompt {
+		m.loopLeavePrompt = commandEmpty
+	}
 	// While exiting (Ctrl+C waiting on the cancelled run's checkpoint flush) a
 	// new run must not start: the deferred tea.Quit would abort it mid-flight
 	// and orphan its checkpoint blobs — the exact loss flushRunIDs prevents.
@@ -3814,6 +3868,14 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 		m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: helpText()})
 		return m, nil
 	case commandClear:
+		// A foreground loop keeps firing after /clear (it wipes the screen, not the
+		// session), so warn once before clearing the context it will run into.
+		if m.loopActive() && m.loopLeavePrompt != commandClear {
+			m.loopLeavePrompt = commandClear
+			m = m.appendLoopSystem(m.loopFooterSummary() + " still running — /clear keeps them firing behind a cleared screen. Run /clear again to confirm, or /loop stop all first.")
+			return m, nil
+		}
+		m.loopLeavePrompt = commandEmpty
 		m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionClear})
 		// Clearing wipes the visible transcript only — the session's context is
 		// intact, so the next prompt still replays the full history. Say so, and
@@ -3822,6 +3884,11 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 		// Scrollback above can't be un-printed; a faint divider marks where the
 		// cleared surface ended and the frontier restarts for the fresh transcript.
 		m.resetFlushFrontier("· cleared ·")
+		// /clear wipes the transcript but not the session, so loops keep running;
+		// say so rather than let them silently fire into a "cleared" screen.
+		if m.loopActive() {
+			m = m.appendLoopSystem(m.loopFooterSummary() + " still running — /loop stop all to end them.")
+		}
 		return m, nil
 	case commandNew:
 		// A fresh session mid-run would strand the in-flight turn's events; make the
@@ -3832,7 +3899,17 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 			return m, nil
 		}
 		return m.startNewSession(), nil
+	case commandLoop:
+		return m.handleLoopCommand(command.text)
 	case commandExit:
+		// Closing the session stops its foreground loops mid-task; warn once so a
+		// token-spending loop isn't ended by reflex.
+		if m.loopActive() && m.loopLeavePrompt != commandExit {
+			m.loopLeavePrompt = commandExit
+			m = m.appendLoopSystem(m.loopFooterSummary() + " active — closing the session stops them. Run /exit again to confirm, or /loop stop all first.")
+			return m, nil
+		}
+		m.loopLeavePrompt = commandEmpty
 		// /exit gets the same protection as Ctrl+C: cancel any in-flight run and
 		// defer the quit until its checkpoint session events flush — quitting
 		// immediately would orphan the blobs and break /rewind.
@@ -3845,6 +3922,15 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 	case commandTools:
 		m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: m.toolsText()})
 		return m, nil
+	case commandSkills:
+		// With skills installed, /skills opens a searchable picker (like /model);
+		// the text card remains only as the no-skills install hint.
+		if picker := m.newSkillPicker(); picker != nil {
+			m.picker = picker
+			return m, nil
+		}
+		m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: m.skillsText()})
+		return m, nil
 	case commandMCP:
 		if strings.TrimSpace(command.text) == "" {
 			return m.openMCPManager(), nil
@@ -4040,6 +4126,11 @@ func (m model) handleSubmit() (tea.Model, tea.Cmd) {
 		if next, cmd, handled := m.handleUserCommand(command.text); handled {
 			return next, cmd
 		}
+		// Then an installed skill: "/<skill-name> [args]" runs the skill directly
+		// (deterministic invocation, vs waiting for the model to pull it in).
+		if next, cmd, handled := m.handleSkillCommand(command.text); handled {
+			return next, cmd
+		}
 		m.transcript = reduceTranscript(m.transcript, transcriptAction{
 			kind: actionAppendError,
 			text: "unknown command: " + command.text,
@@ -4311,6 +4402,21 @@ func (m *model) cancelRun() {
 		m.runCancel()
 	}
 	m.clearStreamingToolCall() // a cancelled file-write must not linger into the next run
+	// A cancelled loop iteration bypasses the agentResponseMsg completion seam (its
+	// late message is drained through flushRunIDs, not advanceLoop), so clear the
+	// loop tag here and re-arm the interrupted loop for its next cadence. Otherwise
+	// the loop is left "running" forever (nextRunAt stays zero) and the NEXT
+	// unrelated turn would be misattributed as this loop's completion.
+	if m.activeLoopID != "" {
+		if l := m.findLoop(m.activeLoopID); l != nil {
+			if l.mode == loopModeSelfPaced {
+				l.nextRunAt = m.now().Add(clampSelfPaceDelay(adaptiveSelfPaceDelay(l.iteration)))
+			} else {
+				l.nextRunAt = m.now().Add(l.interval)
+			}
+		}
+		m.activeLoopID = ""
+	}
 	// Remember the in-flight run — and the session it was recording into — so
 	// its final agentResponseMsg is still drained for session-event persistence
 	// after activeRunID is cleared. Otherwise the checkpoint blobs it captured
@@ -4446,9 +4552,9 @@ func (m model) runAgentWithOptions(runID int, runCtx context.Context, prompt str
 				IncludeLSP:   true,
 				Autonomy:     selfCorrectAutonomyForMode(options.PermissionMode),
 			})
-			// Inline post-edit diagnostics: edit_file/write_file append error
-			// diagnostics for the file they just wrote to their own output, so the
-			// model sees a break in the same turn. Shares the run's lazy manager.
+			// Background post-edit diagnostics: the loop checks files changed by
+			// edit_file/write_file off the tool-call path and nudges the model with
+			// any errors before its next request. Shares the run's lazy manager.
 			options.FileDiagnostics = agent.NewFileDiagnostics(lspManager, options.Cwd)
 		}
 

internal/tui/options.go

@@ -13,6 +13,7 @@ import (
 	"github.com/Gitlawb/zero/internal/providermodeldiscovery"
 	"github.com/Gitlawb/zero/internal/sandbox"
 	"github.com/Gitlawb/zero/internal/sessions"
+	"github.com/Gitlawb/zero/internal/skills"
 	"github.com/Gitlawb/zero/internal/tools"
 	"github.com/Gitlawb/zero/internal/usage"
 	"github.com/Gitlawb/zero/internal/zeroruntime"
@@ -48,7 +49,13 @@ type Options struct {
 	SessionCompactor            SessionCompactor
 	PrService                   *PrService
 
-	AgentOptions    agent.Options
+	AgentOptions agent.Options
+	// LoadSkills returns the installed skills (default skills dir merged with any
+	// plugin skill roots), bodies included, for /skills and direct /<skill-name>
+	// invocation. Called lazily per use so newly installed skills are picked up
+	// without a restart. Nil means the session has no skills wiring (skills stay
+	// model-pulled via the skill tool only).
+	LoadSkills      func() []skills.Skill
 	PermissionMode  agent.PermissionMode
 	ReasoningEffort modelregistry.ReasoningEffort
 	ResponseStyle   string

internal/tui/picker.go

@@ -24,6 +24,7 @@ const (
 	pickerEffort
 	pickerSession
 	pickerTheme
+	pickerSkill
 )
 
 // pickerItem is one selectable row: Label is shown, Value is passed to the
@@ -225,6 +226,35 @@ func (m model) newModelPicker() *commandPicker {
 	return &commandPicker{kind: pickerModel, title: "Choose a model", items: items, allItems: append([]pickerItem{}, items...), selected: 0}
 }
 
+// newSkillPicker lists the installed skills for browse-and-run: type to filter,
+// arrow keys to select, Enter runs the chosen skill immediately. Selection is by
+// the skill's EXACT name (item.Value), so even skills the slash path cannot
+// reach — names shadowed by a builtin or user command, or names that don't fit
+// a slash token — are runnable here: picking from the Skills picker is
+// unambiguous. Returns nil when no skills are installed (the caller falls back
+// to the install-hint card).
+func (m model) newSkillPicker() *commandPicker {
+	installed := m.installedSkills()
+	items := make([]pickerItem, 0, len(installed))
+	for _, skill := range installed {
+		name := strings.TrimSpace(skill.Name)
+		if name == "" {
+			continue
+		}
+		label := name
+		if slash := skillSlashName(name); slash != "" {
+			// Show the slash form where one exists — it doubles as documentation
+			// of the direct "/name [args]" invocation.
+			label = "/" + slash
+		}
+		items = append(items, pickerItem{Label: label, Value: name, Meta: strings.TrimSpace(skill.Description)})
+	}
+	if len(items) == 0 {
+		return nil
+	}
+	return &commandPicker{kind: pickerSkill, title: "pick a skill · ⏎ fills /name — add your request", items: items, allItems: append([]pickerItem{}, items...), selected: 0}
+}
+
 // modelPickerProviders returns the providers to list in /model: all saved
 // providers, falling back to the active profile when none were threaded in.
 func (m model) modelPickerProviders() []config.ProviderProfile {

internal/tui/session.go

@@ -99,6 +99,12 @@ func (m model) startNewSession() model {
 	// Scrollback above can't be un-printed; a faint divider marks the boundary and
 	// the flush frontier restarts for the fresh transcript (mirrors /clear, /resume).
 	m.resetFlushFrontier("· new session ·")
+	// Loops belong to the previous session; stop them so they don't fire the old
+	// conversation's prompt into the fresh one.
+	if updated, cleared := m.clearLoopsForSessionSwitch(); cleared > 0 {
+		m = updated
+		m.transcript = reduceTranscript(m.transcript, transcriptAction{kind: actionAppendSystem, text: fmt.Sprintf("Stopped %d loop(s) tied to the previous session.", cleared)})
+	}
 	return m
 }
 
@@ -123,13 +129,24 @@ func (m model) appendSessionEvent(eventType sessions.EventType, payload any) (mo
 
 func (m model) appendSessionEvents(events []pendingSessionEvent) (model, []transcriptRow) {
 	rows := []transcriptRow{}
+	if m.activeSession.SessionID == "" || len(events) == 0 {
+		return m, rows
+	}
+	inputs := make([]sessions.AppendEventInput, 0, len(events))
 	for _, event := range events {
-		next, err := m.appendSessionEvent(event.Type, event.Payload)
-		if err != nil {
-			rows = append(rows, transcriptRow{kind: rowError, text: "session record error: " + err.Error()})
-			continue
-		}
-		m = next
+		inputs = append(inputs, sessions.AppendEventInput{Type: event.Type, Payload: event.Payload})
+	}
+	appended, err := m.sessionStore.AppendEvents(m.activeSession.SessionID, inputs)
+	if err != nil {
+		rows = append(rows, transcriptRow{kind: rowError, text: "session record error: " + err.Error()})
+		return m, rows
+	}
+	if len(appended) > 0 {
+		last := appended[len(appended)-1]
+		m.activeSession.UpdatedAt = last.CreatedAt
+		m.activeSession.EventCount = last.Sequence
+		m.activeSession.LastEventType = last.Type
+		m.sessionEvents = append(m.sessionEvents, appended...)
 	}
 	return m, rows
 }
@@ -142,13 +159,12 @@ func (m model) appendSessionEventsTo(sessionID string, events []pendingSessionEv
 	if m.sessionStore == nil || sessionID == "" {
 		return rows
 	}
+	inputs := make([]sessions.AppendEventInput, 0, len(events))
 	for _, event := range events {
-		if _, err := m.sessionStore.AppendEvent(sessionID, sessions.AppendEventInput{
-			Type:    event.Type,
-			Payload: event.Payload,
-		}); err != nil {
-			rows = append(rows, transcriptRow{kind: rowError, text: "session record error: " + err.Error()})
-		}
+		inputs = append(inputs, sessions.AppendEventInput{Type: event.Type, Payload: event.Payload})
+	}
+	if _, err := m.sessionStore.AppendEvents(sessionID, inputs); err != nil {
+		rows = append(rows, transcriptRow{kind: rowError, text: "session record error: " + err.Error()})
 	}
 	return rows
 }
@@ -195,6 +211,10 @@ func (m model) handleResumeCommand(args string) (model, string) {
 		return m, "Sessions\nerror: " + err.Error()
 	}
 
+	// Capture the current session id before switching so loops are only torn down
+	// on a real change — `/resume latest` or `/resume <currentID>` can resolve to
+	// the already-active session, whose loops belong to it, not a "previous" one.
+	previousID := m.activeSession.SessionID
 	m.activeSession = *session
 	m.sessionEvents = append([]sessions.Event{}, events...)
 	if m.providerName == "" {
@@ -203,9 +223,16 @@ func (m model) handleResumeCommand(args string) (model, string) {
 	if m.modelName == "" {
 		m.modelName = session.ModelID
 	}
+	loopsCleared := 0
+	if session.SessionID != previousID {
+		m, loopsCleared = m.clearLoopsForSessionSwitch()
+	}
 
 	rows := initialTranscript()
 	rows = appendRow(rows, rowSystem, m.formatResumeSummary(*session, len(events)))
+	if loopsCleared > 0 {
+		rows = appendRow(rows, rowSystem, fmt.Sprintf("Stopped %d loop(s) tied to the previous session.", loopsCleared))
+	}
 	rows = appendTranscriptRowsDedup(rows, transcriptRowsFromSessionEvents(events))
 	m.transcript = rows
 	// Every rehydrated row is settled by construction, so resetting the flush

internal/tui/session_test.go

@@ -108,6 +108,46 @@ func TestPromptSubmitPersistsTUISessionEvents(t *testing.T) {
 	}
 }
 
+func TestAppendSessionEventsBatchesAndUpdatesActiveSession(t *testing.T) {
+	store := testSessionStore(t)
+	session, err := store.Create(sessions.CreateInput{SessionID: "tui_batch", Title: "batch"})
+	if err != nil {
+		t.Fatalf("Create returned error: %v", err)
+	}
+	m := model{
+		sessionStore:  store,
+		activeSession: session,
+	}
+
+	next, rows := m.appendSessionEvents([]pendingSessionEvent{
+		{Type: sessions.EventMessage, Payload: map[string]any{"role": "assistant", "content": "done"}},
+		{Type: sessions.EventUsage, Payload: map[string]any{"totalTokens": 3}},
+	})
+	if len(rows) != 0 {
+		t.Fatalf("appendSessionEvents returned error rows: %#v", rows)
+	}
+	if next.activeSession.EventCount != 2 || next.activeSession.LastEventType != sessions.EventUsage {
+		t.Fatalf("active session metadata not updated from batch: %#v", next.activeSession)
+	}
+	if len(next.sessionEvents) != 2 || next.sessionEvents[0].Sequence != 1 || next.sessionEvents[1].Sequence != 2 {
+		t.Fatalf("in-memory session events not updated from batch: %#v", next.sessionEvents)
+	}
+	events, err := store.ReadEvents(session.SessionID)
+	if err != nil {
+		t.Fatalf("ReadEvents returned error: %v", err)
+	}
+	if got := eventTypes(events); !equalEventTypes(got, []sessions.EventType{sessions.EventMessage, sessions.EventUsage}) {
+		t.Fatalf("unexpected persisted event types: %#v", got)
+	}
+	loaded, err := store.Get(session.SessionID)
+	if err != nil {
+		t.Fatalf("Get returned error: %v", err)
+	}
+	if loaded == nil || loaded.EventCount != next.activeSession.EventCount || loaded.LastEventType != next.activeSession.LastEventType {
+		t.Fatalf("store metadata diverged from active session: store=%#v active=%#v", loaded, next.activeSession)
+	}
+}
+
 func TestPromptWithoutProviderDoesNotCreateSession(t *testing.T) {
 	store := testSessionStore(t)
 	m := newModel(context.Background(), Options{SessionStore: store})

internal/tui/skill_commands.go

@@ -0,0 +1,205 @@
+package tui
+
+import (
+	"strings"
+
+	tea "charm.land/bubbletea/v2"
+
+	"github.com/Gitlawb/zero/internal/skills"
+)
+
+// Skill slash invocation: "/<skill-name> [args]" runs an installed skill
+// directly, mirroring user commands (.zero/commands). Skills were previously
+// model-pulled only (the skill tool), which made invocation a matter of model
+// discretion; typing the skill's name makes it deterministic. Precedence is
+// builtin > user command > skill: parseCommand resolves builtins first, and the
+// commandUnknown fallback tries user commands before skills.
+
+// handleSkillCommand resolves a "/name args" that wasn't a builtin or a user
+// command against the installed skills. On a match it launches a normal agent
+// turn whose prompt inlines the skill body (its instructions) followed by the
+// typed args, returning handled=true. handled=false means no skill matched, so
+// the caller falls through to "unknown command".
+func (m model) handleSkillCommand(raw string) (model, tea.Cmd, bool) {
+	name, args := splitUserCommand(raw)
+	if name == "" {
+		return m, nil, false
+	}
+	skill, ok := m.lookupSkillCommand(name)
+	if !ok {
+		return m, nil, false
+	}
+	body := strings.TrimSpace(skill.Content)
+	if body == "" {
+		// The name matched a real skill, so falling through to "unknown command"
+		// would mislead; surface the actual problem instead.
+		m.transcript = reduceTranscript(m.transcript, transcriptAction{
+			kind: actionAppendError,
+			text: "skill /" + name + " has an empty SKILL.md body (" + skill.Path + ")",
+		})
+		return m, nil, true
+	}
+	return m.launchOrDeferExpandedPrompt(raw, skillInvocationPrompt(body, args))
+}
+
+// bareSkillInvocationNote is appended when a skill is invoked with no request.
+// The body alone is instructions with no target ("review the PR" — which PR?),
+// and without this note the model improvises one instead of asking. The wording
+// is conditional so self-contained skills (no target needed) still just run.
+const bareSkillInvocationNote = "The user invoked this skill directly without providing a request. " +
+	"If these instructions need a target or details that are not already clear from the conversation " +
+	"(which pull request, file, branch, topic, …), ask for them first — do not guess or pick one yourself. " +
+	"If the instructions are self-contained, proceed."
+
+// skillInvocationPrompt builds the agent prompt for a skill invocation: the
+// skill body (its instructions), then either the user's request or — for a bare
+// invocation — the ask-first note above. Mirrors usercommands.Expand's
+// no-placeholder behavior for the args case.
+func skillInvocationPrompt(body, args string) string {
+	if args != "" {
+		return body + "\n\n" + args
+	}
+	return body + "\n\n" + bareSkillInvocationNote
+}
+
+// launchOrDeferExpandedPrompt applies the same run-state guards the plain
+// commandPrompt path has to an expanded (user command / skill) prompt: while
+// exiting nothing may start, a prompt submitted mid-run is queued for the next
+// turn, and compaction-in-flight warns instead of racing the compactor. The
+// EXPANDED prompt is what gets queued — the queue flush path resubmits text as
+// a literal prompt, so queuing the raw "/name args" would send it to the model
+// as prose instead of re-dispatching it. raw is the typed invocation; on the
+// compaction warning it is restored into the composer for an easy re-submit
+// (the commandUnknown dispatch cleared the composer before we got here, unlike
+// the plain-prompt path whose guard fires before the clear). Empty raw (the
+// picker path has no typed form) restores nothing.
+func (m model) launchOrDeferExpandedPrompt(raw, prompt string) (model, tea.Cmd, bool) {
+	if m.exiting {
+		return m, nil, true
+	}
+	if m.pending {
+		return m.queueMessage(prompt), nil, true
+	}
+	if m.compactInFlight {
+		if strings.TrimSpace(raw) != "" {
+			m.input.SetValue(raw)
+			m.input.CursorEnd()
+		}
+		m.transcript = reduceTranscript(m.transcript, transcriptAction{
+			kind: actionAppendSystem,
+			text: "Compact\nstatus: warning\nCompaction is running. Re-run the command when it finishes.",
+		})
+		return m, nil, true
+	}
+	next, teaCmd := m.launchPrompt(prompt)
+	return next, teaCmd, true
+}
+
+// takenSlashNames returns every slash token already claimed by a builtin
+// command (or alias) or a user command — the names a typed "/x" would dispatch
+// to before ever reaching a skill.
+func (m model) takenSlashNames() map[string]bool {
+	taken := map[string]bool{}
+	for _, command := range commandDefinitions {
+		taken[strings.TrimPrefix(command.name, "/")] = true
+		for _, alias := range command.aliases {
+			taken[strings.TrimPrefix(alias, "/")] = true
+		}
+	}
+	for _, cmd := range m.userCommands {
+		taken[cmd.Name] = true
+	}
+	return taken
+}
+
+// chooseSkillFromPicker handles Enter on a skill-picker row. Most skills want a
+// request ("review WHICH pr?"), so selection fills the composer with
+// "/name " — cursor at the end — for the user to complete and submit (Enter
+// again runs it bare). Skills whose names cannot be typed as a slash command
+// (non-slash shapes, or names shadowed by a builtin or user command) fall back
+// to running immediately: the picker is the only path that reaches them, and an
+// unfillable composer would be a dead end.
+func (m model) chooseSkillFromPicker(item pickerItem) (model, tea.Cmd) {
+	slash := skillSlashName(item.Value)
+	if slash == "" || m.takenSlashNames()[slash] {
+		return m.invokeSkillByName(item.Value)
+	}
+	m.input.SetValue("/" + slash + " ")
+	m.input.CursorEnd()
+	return m, nil
+}
+
+// invokeSkillByName runs the installed skill with the given EXACT raw name (the
+// skill-picker path). The same run-state guards as slash invocation apply; the
+// picker offers no args affordance, so the prompt is the skill body alone.
+func (m model) invokeSkillByName(name string) (model, tea.Cmd) {
+	for _, skill := range m.installedSkills() {
+		if strings.TrimSpace(skill.Name) != name {
+			continue
+		}
+		body := strings.TrimSpace(skill.Content)
+		if body == "" {
+			m.transcript = reduceTranscript(m.transcript, transcriptAction{
+				kind: actionAppendError,
+				text: "skill " + name + " has an empty SKILL.md body (" + skill.Path + ")",
+			})
+			return m, nil
+		}
+		next, teaCmd, _ := m.launchOrDeferExpandedPrompt("", skillInvocationPrompt(body, ""))
+		return next, teaCmd
+	}
+	// The picker row came from a slightly older load (TTL cache) and the skill
+	// has since been removed.
+	m.transcript = reduceTranscript(m.transcript, transcriptAction{
+		kind: actionAppendError,
+		text: "skill " + name + " is no longer installed",
+	})
+	return m, nil
+}
+
+// lookupSkillCommand returns the installed skill whose slash name matches the
+// given (lowercased) name. Linear scan over a fresh load — skills are re-read
+// per invocation so a skill installed mid-session is invocable without a
+// restart, and the body is never held on the model.
+func (m model) lookupSkillCommand(name string) (skills.Skill, bool) {
+	name = strings.ToLower(strings.TrimSpace(name))
+	if name == "" {
+		return skills.Skill{}, false
+	}
+	for _, skill := range m.installedSkills() {
+		if skillSlashName(skill.Name) == name {
+			return skill, true
+		}
+	}
+	return skills.Skill{}, false
+}
+
+// installedSkills returns the session's installed skills (default dir merged
+// with plugin skill roots) via the injected loader, or nil when the session has
+// no skills wiring (e.g. bare test models).
+func (m model) installedSkills() []skills.Skill {
+	if m.loadSkills == nil {
+		return nil
+	}
+	return m.loadSkills()
+}
+
+// skillSlashName maps a skill's frontmatter name to its slash-command form:
+// lowercased, and only if it fits the slash-token shape (letters, digits,
+// dot/underscore/hyphen — a superset of user-command names, since skill names
+// are free-form frontmatter). Returns "" for names that cannot be typed as a
+// /command (e.g. containing spaces); those skills remain loadable by the model
+// via the skill tool and are still listed by /skills.
+func skillSlashName(name string) string {
+	name = strings.ToLower(strings.TrimSpace(name))
+	if name == "" {
+		return ""
+	}
+	for _, r := range name {
+		valid := (r >= 'a' && r <= 'z') || (r >= '0' && r <= '9') || r == '-' || r == '_' || r == '.'
+		if !valid {
+			return ""
+		}
+	}
+	return name
+}

internal/tui/skill_commands_test.go

@@ -0,0 +1,412 @@
+package tui
+
+import (
+	"context"
+	"strings"
+	"testing"
+
+	tea "charm.land/bubbletea/v2"
+
+	"github.com/Gitlawb/zero/internal/agent"
+	"github.com/Gitlawb/zero/internal/skills"
+)
+
+// newSkillTestModel builds a model with an injected skills loader (and the
+// matching palette metadata), no filesystem involved.
+func newSkillTestModel(t *testing.T, installed ...skills.Skill) model {
+	t.Helper()
+	infos := make([]agent.SkillInfo, 0, len(installed))
+	for _, s := range installed {
+		infos = append(infos, agent.SkillInfo{Name: s.Name, Description: s.Description})
+	}
+	return newModel(context.Background(), Options{
+		Cwd:          t.TempDir(),
+		LoadSkills:   func() []skills.Skill { return installed },
+		AgentOptions: agent.Options{Skills: infos},
+	})
+}
+
+func submitInput(t *testing.T, m model, input string) model {
+	t.Helper()
+	m.input.SetValue(input)
+	updated, _ := m.Update(testKey(tea.KeyEnter))
+	return updated.(model)
+}
+
+func TestSkillCommandInvokesAndSubmits(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{
+		Name:        "deploy-checks",
+		Description: "Run the pre-deploy verification suite.",
+		Content:     "Run every verification step and summarize failures.",
+		Path:        "/skills/deploy-checks/SKILL.md",
+	})
+
+	next := submitInput(t, m, "/deploy-checks ship v2 to production")
+
+	if transcriptContains(next.transcript, "unknown command") {
+		t.Fatalf("an installed skill must not be 'unknown', got %#v", next.transcript)
+	}
+	if !transcriptContains(next.transcript, "Run every verification step and summarize failures.") {
+		t.Fatalf("skill body should be inlined into the prompt, got %#v", next.transcript)
+	}
+	if !transcriptContains(next.transcript, "ship v2 to production") {
+		t.Fatalf("typed args should follow the skill body, got %#v", next.transcript)
+	}
+}
+
+func TestSkillCommandWithoutArgs(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review the diff for correctness."})
+
+	next := submitInput(t, m, "/reviewer")
+
+	if !transcriptContains(next.transcript, "Review the diff for correctness.") {
+		t.Fatalf("bare skill invocation should submit the body, got %#v", next.transcript)
+	}
+	// A bare invocation carries the ask-first note: instructions with no target
+	// must make the model ask ("which PR?") instead of improvising one.
+	if !transcriptContains(next.transcript, "ask for them first") {
+		t.Fatalf("bare invocation should carry the clarify-first note, got %#v", next.transcript)
+	}
+}
+
+// An invocation WITH a request must not carry the ask-first note — the user
+// already said what to apply the skill to.
+func TestSkillCommandWithArgsHasNoClarifyNote(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review the diff."})
+
+	next := submitInput(t, m, "/reviewer PR 484 reconnect changes")
+
+	if transcriptContains(next.transcript, "ask for them first") {
+		t.Fatalf("args invocation must not carry the clarify note, got %#v", next.transcript)
+	}
+}
+
+// A skill's frontmatter name is free-form; invocation matches its lowercased
+// slash form.
+func TestSkillCommandNameIsCaseInsensitive(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "Deploy-Checks", Content: "Check things."})
+
+	next := submitInput(t, m, "/deploy-checks")
+
+	if !transcriptContains(next.transcript, "Check things.") {
+		t.Fatalf("uppercase frontmatter name should be invocable lowercased, got %#v", next.transcript)
+	}
+}
+
+// Precedence: a user command (.zero/commands) shadows a same-named skill.
+func TestUserCommandShadowsSkill(t *testing.T) {
+	root := t.TempDir()
+	writeUserCommand(t, root, "greet.md", "Say hello from the user command.")
+	m := newModel(context.Background(), Options{
+		Cwd:        root,
+		LoadSkills: func() []skills.Skill { return []skills.Skill{{Name: "greet", Content: "Skill body must not run."}} },
+	})
+
+	next := submitInput(t, m, "/greet")
+
+	if !transcriptContains(next.transcript, "Say hello from the user command.") {
+		t.Fatalf("user command should win the name collision, got %#v", next.transcript)
+	}
+	if transcriptContains(next.transcript, "Skill body must not run.") {
+		t.Fatalf("shadowed skill must not run, got %#v", next.transcript)
+	}
+}
+
+// An empty skill body is a real, named match — surface the problem instead of
+// falling through to a misleading "unknown command".
+func TestSkillCommandEmptyBody(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "hollow", Path: "/skills/hollow/SKILL.md"})
+
+	next := submitInput(t, m, "/hollow")
+
+	if transcriptContains(next.transcript, "unknown command") {
+		t.Fatalf("an empty skill must not be 'unknown', got %#v", next.transcript)
+	}
+	if !transcriptContains(next.transcript, "empty SKILL.md body") {
+		t.Fatalf("empty-body error should be surfaced, got %#v", next.transcript)
+	}
+}
+
+func TestUnknownSlashStillUnknownWithSkillsInstalled(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review."})
+
+	next := submitInput(t, m, "/definitelynotaskill")
+
+	if !transcriptContains(next.transcript, "unknown command") {
+		t.Fatalf("non-matching name should still be unknown, got %#v", next.transcript)
+	}
+}
+
+func TestSkillSlashName(t *testing.T) {
+	cases := map[string]string{
+		"deploy-checks":  "deploy-checks",
+		"Deploy-Checks":  "deploy-checks",
+		"  pdf_tools  ":  "pdf_tools",
+		"v2.migrate":     "v2.migrate",
+		"has space":      "",
+		"emoji✨":         "",
+		"":               "",
+		"slash/inside":   "",
+		"tab\tseparated": "",
+	}
+	for in, want := range cases {
+		if got := skillSlashName(in); got != want {
+			t.Errorf("skillSlashName(%q) = %q, want %q", in, got, want)
+		}
+	}
+}
+
+func TestSkillAppearsInAutocomplete(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "deploy-checks", Description: "Run the pre-deploy suite.", Content: "x"})
+
+	got := m.matchCommandSuggestions("/dep")
+	found := false
+	for _, s := range got {
+		if s.Name == "/deploy-checks" {
+			found = true
+			if s.Desc != "Run the pre-deploy suite. (skill)" {
+				t.Fatalf("skill suggestion should be labeled, got %q", s.Desc)
+			}
+		}
+	}
+	if !found {
+		t.Fatalf("skill /deploy-checks should appear for '/dep', got %#v", got)
+	}
+}
+
+// A skill shadowed by a builtin (or its alias) or a user command would be dead
+// at dispatch time, so the palette must not advertise it.
+func TestShadowedSkillNotSuggested(t *testing.T) {
+	root := t.TempDir()
+	writeUserCommand(t, root, "deploy.md", "User deploy.")
+	installed := []skills.Skill{
+		{Name: "help", Content: "x"},     // builtin collision
+		{Name: "sessions", Content: "x"}, // builtin ALIAS collision (/resume alias)
+		{Name: "deploy", Content: "x"},   // user-command collision
+	}
+	infos := make([]agent.SkillInfo, 0, len(installed))
+	for _, s := range installed {
+		infos = append(infos, agent.SkillInfo{Name: s.Name})
+	}
+	m := newModel(context.Background(), Options{
+		Cwd:          root,
+		LoadSkills:   func() []skills.Skill { return installed },
+		AgentOptions: agent.Options{Skills: infos},
+	})
+
+	// Assert on the advertised NAME with a skill-marked Desc, not on the exact
+	// fallback Desc format — the invariant is that no skill row carries a
+	// builtin/user-command name, regardless of description wording.
+	for _, token := range []string{"/hel", "/ses", "/dep"} {
+		for _, s := range m.matchSkillSuggestions(token) {
+			if s.Name == "/help" || s.Name == "/sessions" || s.Name == "/deploy" {
+				t.Fatalf("shadowed skill advertised for %q: %#v", token, s)
+			}
+		}
+	}
+}
+
+// Invalid slash shapes (spaces etc.) and a bare "/" must not surface skills.
+func TestSkillSuggestionEdgeCases(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "has space", Description: "not invocable", Content: "x"})
+
+	if got := m.matchSkillSuggestions("/has"); len(got) != 0 {
+		t.Fatalf("invalid slash-shape skill must not be suggested, got %#v", got)
+	}
+	if got := m.matchSkillSuggestions("/"); got != nil {
+		t.Fatalf("bare '/' should not list skills, got %#v", got)
+	}
+}
+
+func TestSkillsCommandResolves(t *testing.T) {
+	command, ok := resolveCommand("/skills")
+	if !ok || command.kind != commandSkills {
+		t.Fatalf("resolveCommand(/skills) = %#v, %v", command, ok)
+	}
+}
+
+// With skills installed, /skills opens a searchable picker (like /model).
+func TestSkillsCommandOpensPicker(t *testing.T) {
+	m := newSkillTestModel(t,
+		skills.Skill{Name: "deploy-checks", Description: "Run the pre-deploy suite.", Content: "x"},
+		skills.Skill{Name: "has space", Description: "tool-only skill", Content: "x"},
+	)
+
+	next := submitInput(t, m, "/skills")
+
+	if next.picker == nil || next.picker.kind != pickerSkill {
+		t.Fatalf("/skills should open the skill picker, got %#v", next.picker)
+	}
+	labels := map[string]string{}
+	for _, item := range next.picker.items {
+		labels[item.Label] = item.Value
+	}
+	if labels["/deploy-checks"] != "deploy-checks" {
+		t.Fatalf("slash-invocable skill should show its slash form, got %#v", labels)
+	}
+	// A non-slash-shaped name is still selectable (bare label, exact-name value).
+	if labels["has space"] != "has space" {
+		t.Fatalf("non-slash skill should be listed bare but selectable, got %#v", labels)
+	}
+}
+
+// Enter on a picker row fills the composer with "/name " so the user can add
+// their request (which PR? which file?) before submitting — it must NOT fire
+// the skill with no request attached.
+func TestSkillPickerEnterFillsComposer(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review the diff for correctness."})
+
+	next := submitInput(t, m, "/skills")
+	if next.picker == nil {
+		t.Fatal("picker should be open")
+	}
+	updated, _ := next.Update(testKey(tea.KeyEnter))
+	after := updated.(model)
+
+	if after.picker != nil {
+		t.Fatal("picker should close on Enter")
+	}
+	if got := after.input.Value(); got != "/reviewer " {
+		t.Fatalf("composer should be filled with the invocation, got %q", got)
+	}
+	if transcriptContains(after.transcript, "Review the diff for correctness.") {
+		t.Fatalf("skill must not run before the user submits, got %#v", after.transcript)
+	}
+
+	// A second Enter submits the (bare) invocation and runs the skill.
+	final, _ := after.Update(testKey(tea.KeyEnter))
+	done := final.(model)
+	if !transcriptContains(done.transcript, "Review the diff for correctness.") {
+		t.Fatalf("submitting the filled composer should run the skill, got %#v", done.transcript)
+	}
+}
+
+// Picker selection is by exact name, so a skill shadowed by a builtin (dead on
+// the slash path) is still runnable from the picker.
+func TestSkillPickerRunsBuiltinShadowedSkill(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "help", Description: "shadowed", Content: "Shadowed skill body."})
+
+	next := submitInput(t, m, "/skills")
+	if next.picker == nil {
+		t.Fatal("picker should be open")
+	}
+	updated, _ := next.Update(testKey(tea.KeyEnter))
+	after := updated.(model)
+
+	if !transcriptContains(after.transcript, "Shadowed skill body.") {
+		t.Fatalf("picker must run the shadowed skill directly, got %#v", after.transcript)
+	}
+}
+
+func TestSkillsCommandEmptyState(t *testing.T) {
+	m := newModel(context.Background(), Options{Cwd: t.TempDir()})
+
+	next := submitInput(t, m, "/skills")
+
+	if !transcriptContains(next.transcript, "No skills installed.") {
+		t.Fatalf("empty state should say no skills, got %#v", next.transcript)
+	}
+}
+
+// Run-state guards: an expanded skill prompt must not race an active run — it
+// queues (as the EXPANDED prompt, since the queue flush submits literal text).
+func TestSkillInvocationQueuedWhileRunPending(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review the diff."})
+	m.pending = true
+
+	next, _, handled := m.handleSkillCommand("/reviewer focus on tests")
+	if !handled {
+		t.Fatal("skill must be handled even while a run is pending")
+	}
+	if next.queuedMessage == "" || !strings.Contains(next.queuedMessage, "Review the diff.") {
+		t.Fatalf("expanded prompt should be queued, got %q", next.queuedMessage)
+	}
+	if !strings.Contains(next.queuedMessage, "focus on tests") {
+		t.Fatalf("queued prompt should carry the args, got %q", next.queuedMessage)
+	}
+}
+
+func TestSkillInvocationDroppedWhileExiting(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review."})
+	m.exiting = true
+
+	next, cmd, handled := m.handleSkillCommand("/reviewer")
+	if !handled || cmd != nil || next.queuedMessage != "" {
+		t.Fatalf("exiting must swallow the invocation: handled=%v cmd=%v queued=%q", handled, cmd, next.queuedMessage)
+	}
+}
+
+func TestSkillInvocationWarnsDuringCompaction(t *testing.T) {
+	m := newSkillTestModel(t, skills.Skill{Name: "reviewer", Content: "Review."})
+	m.compactInFlight = true
+
+	next, _, handled := m.handleSkillCommand("/reviewer")
+	if !handled {
+		t.Fatal("skill must be handled during compaction")
+	}
+	if !transcriptContains(next.transcript, "Compaction is running") {
+		t.Fatalf("compaction warning expected, got %#v", next.transcript)
+	}
+	// The typed invocation is restored for an easy re-submit (the dispatch path
+	// cleared the composer before the guard could fire).
+	if got := next.input.Value(); got != "/reviewer" {
+		t.Fatalf("typed invocation should be restored into the composer, got %q", got)
+	}
+}
+
+// The same guard now protects user commands (previously they could start a
+// second concurrent run).
+func TestUserCommandQueuedWhileRunPending(t *testing.T) {
+	root := t.TempDir()
+	writeUserCommand(t, root, "greet.md", "Say hello to $1.")
+	m := newModel(context.Background(), Options{Cwd: root})
+	m.pending = true
+
+	next, _, handled := m.handleUserCommand("/greet world")
+	if !handled {
+		t.Fatal("user command must be handled while pending")
+	}
+	if !strings.Contains(next.queuedMessage, "Say hello to world.") {
+		t.Fatalf("expanded user-command prompt should be queued, got %q", next.queuedMessage)
+	}
+}
+
+// Two skills whose names collide after lowercasing map to one slash name; only
+// the one dispatch will run may be advertised.
+func TestCaseCollidingSkillsAdvertisedOnce(t *testing.T) {
+	m := newSkillTestModel(t,
+		skills.Skill{Name: "Deploy", Description: "wins", Content: "a"},
+		skills.Skill{Name: "deploy", Description: "loses", Content: "b"},
+	)
+
+	rows := 0
+	for _, s := range m.matchSkillSuggestions("/dep") {
+		if s.Name == "/deploy" {
+			rows++
+			if !strings.Contains(s.Desc, "wins") {
+				t.Fatalf("advertised row must describe the skill dispatch runs, got %q", s.Desc)
+			}
+		}
+	}
+	if rows != 1 {
+		t.Fatalf("case-colliding skills must yield exactly one /deploy row, got %d", rows)
+	}
+}
+
+// The palette reads through the loader, so a skill installed mid-session (the
+// loader's next result) appears without a restart.
+func TestSkillPaletteReadsThroughLoader(t *testing.T) {
+	installed := []skills.Skill{}
+	m := newModel(context.Background(), Options{
+		Cwd:        t.TempDir(),
+		LoadSkills: func() []skills.Skill { return installed },
+	})
+	if got := m.matchSkillSuggestions("/lat"); len(got) != 0 {
+		t.Fatalf("no skills installed yet, got %#v", got)
+	}
+	installed = append(installed, skills.Skill{Name: "late-arrival", Description: "installed mid-session", Content: "x"})
+	got := m.matchSkillSuggestions("/lat")
+	if len(got) != 1 || got[0].Name != "/late-arrival" {
+		t.Fatalf("mid-session skill should appear via the loader, got %#v", got)
+	}
+}

internal/tui/user_commands.go

@@ -30,8 +30,9 @@ func (m model) handleUserCommand(raw string) (model, tea.Cmd, bool) {
 	if strings.TrimSpace(prompt) == "" {
 		return m, nil, false
 	}
-	next, teaCmd := m.launchPrompt(prompt)
-	return next, teaCmd, true
+	// Same run-state guards as a plain prompt: a user command invoked mid-run is
+	// queued (as its expanded prompt), not raced into a second concurrent turn.
+	return m.launchOrDeferExpandedPrompt(raw, prompt)
 }
 
 // lookupUserCommand returns the loaded user command with the given (lowercased)

internal/tui/view.go

@@ -218,6 +218,13 @@ func (m model) statusLine(width int) string {
 	} else if summary := m.backgroundTerminalSummary(); summary != "" {
 		left += separator + zeroTheme.muted.Render(summary)
 	}
+	// Active loops surface a persistent "↻ N loops · next 3:05pm" segment so a
+	// running loop is always visible (hidden during an exit/cancel confirm above).
+	if !m.exitConfirmActive && !m.cancelConfirmActive {
+		if loopSummary := m.loopFooterSummary(); loopSummary != "" {
+			left += separator + zeroTheme.accent.Render("↻ ") + zeroTheme.muted.Render(loopSummary)
+		}
+	}
 
 	rightGroups := []string{}
 	// Context-fill gauge: surface it down to the narrow tier (where it matters

scripts/action-summary.mjs

@@ -0,0 +1,83 @@
+#!/usr/bin/env node
+
+import { readFileSync } from 'node:fs';
+import { resolve } from 'node:path';
+import { pathToFileURL } from 'node:url';
+
+const SUMMARY_LIMIT = 280;
+const STRUCTURED_FORMATS = new Set(['json', 'stream-json']);
+
+function normalizeSummary(value) {
+  return String(value ?? '')
+    .replace(/\s+/g, ' ')
+    .trim()
+    .slice(0, SUMMARY_LIMIT);
+}
+
+function truncateSummary(value) {
+  return String(value ?? '').slice(0, SUMMARY_LIMIT);
+}
+
+function lastNonEmptyLine(contents) {
+  let last = '';
+  for (const line of String(contents ?? '').split(/\r?\n/)) {
+    if (line.trim()) {
+      last = line;
+    }
+  }
+  return last;
+}
+
+function summarizeStructured(contents) {
+  let summary;
+
+  for (const line of String(contents ?? '').split(/\r?\n/)) {
+    if (!line.trim()) {
+      continue;
+    }
+
+    let event;
+    try {
+      event = JSON.parse(line);
+    } catch {
+      continue;
+    }
+
+    if (event?.type === 'final' && typeof event.text === 'string') {
+      summary = event.text;
+    } else if (event?.type === 'error' && typeof event.message === 'string') {
+      summary = event.message;
+    }
+  }
+
+  if (summary !== undefined) {
+    return normalizeSummary(summary);
+  }
+  return normalizeSummary(lastNonEmptyLine(contents));
+}
+
+export function summarizeOutput(format, contents) {
+  const normalizedFormat = String(format ?? 'text').toLowerCase();
+  if (!STRUCTURED_FORMATS.has(normalizedFormat)) {
+    return truncateSummary(lastNonEmptyLine(contents));
+  }
+  return summarizeStructured(contents);
+}
+
+function isMainModule() {
+  return (
+    process.argv[1] !== undefined &&
+    pathToFileURL(resolve(process.argv[1])).href === import.meta.url
+  );
+}
+
+if (isMainModule()) {
+  const [format, outputFile] = process.argv.slice(2);
+  let contents = '';
+  try {
+    contents = readFileSync(outputFile, 'utf8');
+  } catch {
+    contents = '';
+  }
+  process.stdout.write(`${summarizeOutput(format, contents)}\n`);
+}

scripts/action-summary.test.mjs

@@ -0,0 +1,148 @@
+import test from 'node:test';
+import assert from 'node:assert/strict';
+import { spawnSync } from 'node:child_process';
+import { mkdtempSync, rmSync, writeFileSync } from 'node:fs';
+import { tmpdir } from 'node:os';
+import { join } from 'node:path';
+import { fileURLToPath } from 'node:url';
+
+import { summarizeOutput } from './action-summary.mjs';
+
+const scriptPath = fileURLToPath(new URL('./action-summary.mjs', import.meta.url));
+const repoRoot = fileURLToPath(new URL('..', import.meta.url));
+
+function jsonl(events) {
+  return events.map((event) => JSON.stringify(event)).join('\n');
+}
+
+test('stream-json final followed by run_end returns final text', () => {
+  const output = jsonl([
+    { type: 'final', text: 'Done. Tests passed.' },
+    { type: 'run_end', status: 'success', exitCode: 0 },
+  ]);
+
+  assert.equal(summarizeOutput('stream-json', output), 'Done. Tests passed.');
+});
+
+test('stream-json error followed by run_end returns error message', () => {
+  const output = jsonl([
+    { type: 'error', code: 'provider_error', message: 'provider request failed' },
+    { type: 'run_end', status: 'error', exitCode: 3 },
+  ]);
+
+  assert.equal(summarizeOutput('stream-json', output), 'provider request failed');
+});
+
+test('stream-json final then error returns error message', () => {
+  const output = jsonl([
+    { type: 'final', text: 'partial answer' },
+    { type: 'error', code: 'incomplete', message: 'run stopped with work unfinished' },
+    { type: 'run_end', status: 'incomplete', exitCode: 4 },
+  ]);
+
+  assert.equal(summarizeOutput('stream-json', output), 'run stopped with work unfinished');
+});
+
+test('json final followed by done returns final text', () => {
+  const output = jsonl([
+    { type: 'final', text: 'Review complete.' },
+    { type: 'done', exit_code: 0 },
+  ]);
+
+  assert.equal(summarizeOutput('json', output), 'Review complete.');
+});
+
+test('json error followed by done returns error message', () => {
+  const output = jsonl([
+    { type: 'error', code: 'exec_failed', message: 'command failed' },
+    { type: 'done', exit_code: 1 },
+  ]);
+
+  assert.equal(summarizeOutput('json', output), 'command failed');
+});
+
+test('json final then error returns error message', () => {
+  const output = jsonl([
+    { type: 'final', text: 'partial answer' },
+    { type: 'error', code: 'incomplete', message: 'run stopped with work unfinished' },
+    { type: 'done', exit_code: 4 },
+  ]);
+
+  assert.equal(summarizeOutput('json', output), 'run stopped with work unfinished');
+});
+
+test('text output returns last non-empty line', () => {
+  const output = '\nfirst line\n\n  final streamed line  \n';
+
+  assert.equal(summarizeOutput('text', output), '  final streamed line  ');
+});
+
+test('unknown format falls back to text behavior', () => {
+  const output = 'alpha\n  beta  \n';
+
+  assert.equal(summarizeOutput('xml', output), '  beta  ');
+});
+
+test('malformed structured output falls back safely', () => {
+  const output = '{not-json}\nraw fallback\n';
+
+  assert.equal(summarizeOutput('stream-json', output), 'raw fallback');
+});
+
+test('long multiline final becomes one-line 280-char summary', () => {
+  const text = `first line\n${'x'.repeat(400)}`;
+  const summary = summarizeOutput('stream-json', jsonl([{ type: 'final', text }]));
+
+  assert.equal(summary.length, 280);
+  assert.equal(summary.includes('\n'), false);
+  assert.equal(summary, `first line ${'x'.repeat(400)}`.slice(0, 280));
+});
+
+test('cli reads output file and prints summary', () => {
+  const dir = mkdtempSync(join(tmpdir(), 'zero-action-summary-'));
+  try {
+    const outputFile = join(dir, 'zero-output.jsonl');
+    writeFileSync(
+      outputFile,
+      jsonl([
+        { type: 'final', text: 'CLI summary' },
+        { type: 'run_end', status: 'success', exitCode: 0 },
+      ]),
+    );
+
+    const result = spawnSync(process.execPath, [scriptPath, 'stream-json', outputFile], {
+      encoding: 'utf8',
+    });
+
+    assert.equal(result.status, 0);
+    assert.equal(result.stderr, '');
+    assert.equal(result.stdout, 'CLI summary\n');
+  } finally {
+    rmSync(dir, { recursive: true, force: true });
+  }
+});
+
+test('cli runs when invoked with relative script path', () => {
+  const dir = mkdtempSync(join(tmpdir(), 'zero-action-summary-'));
+  try {
+    const outputFile = join(dir, 'zero-output.jsonl');
+    writeFileSync(
+      outputFile,
+      jsonl([
+        { type: 'final', text: 'relative CLI summary' },
+        { type: 'run_end', status: 'success', exitCode: 0 },
+      ]),
+    );
+
+    const result = spawnSync(process.execPath, ['scripts/action-summary.mjs', 'stream-json', outputFile], {
+      cwd: repoRoot,
+      encoding: 'utf8',
+    });
+
+    assert.equal(result.status, 0);
+    assert.equal(result.stderr, '');
+    assert.equal(result.stdout, 'relative CLI summary\n');
+  } finally {
+    rmSync(dir, { recursive: true, force: true });
+  }
+});