fix(agent): tell the user a prefix approval leaves the sandbox

Approving a command prefix does not only stop the prompt from reappearing.
shellExecutionArgsForApproval rewrites the call to require_escalated, which
resolves to a nil sandbox engine, so the command runs unsandboxed on the host.
The engine's escalation gate is then satisfied by the PermissionGranted flag
from the approval the user just gave for the sandboxed form.

The escalation itself is deliberate and guarded: proposedCommandPrefix refuses
to offer a prefix when any other segment of the command is not known-safe,
precisely because approval covers the whole command. The defect is that the
prompt never said so. The user chose "allow command prefix for session" and got
"and also run it outside the sandbox".

So this discloses rather than removes. PermissionRequest gains
PrefixApprovalEscalates, computed by shellPrefixApprovalEscalates from the same
guards the rewrite consults, and the two prefix options append "(runs outside
the sandbox)" when it is set. Both the TUI and the ACP path carry it, since an
editor user decides on the same terms as a terminal user.

The main test asserts the disclosure and the rewrite agree on every input
rather than checking each against a fixed expectation, so the two cannot drift
apart later. Verified by mutation: reverting the helper to always-false fails
it, as does making the label unconditional.

internal/acp/permission.go

@@ -25,7 +25,7 @@ func buildPermissionOptions(req agent.PermissionRequest) []PermissionOption {
 	}
 	options := make([]PermissionOption, 0, len(actions))
 	for _, action := range actions {
-		kind, name := optionKindFor(action)
+		kind, name := optionKindFor(action, req.PrefixApprovalEscalates)
 		if kind == "" {
 			continue // skip actions that have no clean ACP option (e.g. cancel)
 		}
@@ -41,18 +41,24 @@ func buildPermissionOptions(req agent.PermissionRequest) []PermissionOption {
 // optionKindFor maps a ZERO decision action to an ACP PermissionOptionKind and a
 // human label. Returns an empty kind for actions that ACP expresses through the
 // outcome rather than an option (cancel).
-func optionKindFor(action agent.PermissionDecisionAction) (kind, name string) {
+//
+// escalates reports that approving a command prefix will also run the command
+// outside the sandbox. The two prefix options say so in their label, since the
+// label is all an ACP client shows and the option id carries no room for it. An
+// editor user is deciding on exactly the same terms as a terminal user, so the
+// disclosure cannot be TUI-only.
+func optionKindFor(action agent.PermissionDecisionAction, escalates bool) (kind, name string) {
 	switch action {
 	case agent.PermissionDecisionAllow, agent.PermissionDecisionAllowStrict:
 		return PermAllowOnce, "Allow"
 	case agent.PermissionDecisionAllowForSession:
 		return PermAllowAlways, "Allow for this session"
 	case agent.PermissionDecisionAllowPrefix:
-		return PermAllowAlways, "Allow this command for the session"
+		return PermAllowAlways, withSandboxEscalationNote("Allow this command for the session", escalates)
 	case agent.PermissionDecisionAlwaysAllow:
 		return PermAllowAlways, "Always allow"
 	case agent.PermissionDecisionAlwaysAllowPrefix:
-		return PermAllowAlways, "Always allow this command"
+		return PermAllowAlways, withSandboxEscalationNote("Always allow this command", escalates)
 	case agent.PermissionDecisionDeny:
 		return PermRejectOnce, "Reject"
 	case agent.PermissionDecisionCancel:
@@ -123,3 +129,13 @@ func rawInputBytes(data []byte) json.RawMessage {
 	}
 	return json.RawMessage(data)
 }
+
+// withSandboxEscalationNote appends the escalation disclosure to a prefix
+// option's label. Kept parallel to the TUI's wording so the same consequence is
+// not described two different ways depending on which client the user runs.
+func withSandboxEscalationNote(name string, escalates bool) string {
+	if !escalates {
+		return name
+	}
+	return name + " (runs outside the sandbox)"
+}

internal/acp/permission_escalation_test.go

@@ -0,0 +1,68 @@
+package acp
+
+import (
+	"strings"
+	"testing"
+
+	"github.com/Gitlawb/zero/internal/agent"
+)
+
+func escalationRequest(escalates bool) agent.PermissionRequest {
+	return agent.PermissionRequest{
+		ToolName: "bash",
+		AvailableDecisions: []agent.PermissionDecisionAction{
+			agent.PermissionDecisionAllow,
+			agent.PermissionDecisionAllowPrefix,
+			agent.PermissionDecisionAlwaysAllowPrefix,
+			agent.PermissionDecisionDeny,
+		},
+		PrefixApprovalEscalates: escalates,
+	}
+}
+
+// An ACP client renders only Name, so if the escalation is not in the label the
+// editor user approves it blind. They face exactly the outcome a terminal user
+// faces, so the disclosure has to reach both clients or it is not a fix.
+func TestACPPrefixOptionsDiscloseLeavingTheSandbox(t *testing.T) {
+	found := 0
+	for _, option := range buildPermissionOptions(escalationRequest(true)) {
+		action := agent.PermissionDecisionAction(option.OptionID)
+		if action != agent.PermissionDecisionAllowPrefix && action != agent.PermissionDecisionAlwaysAllowPrefix {
+			if strings.Contains(option.Name, "sandbox") {
+				t.Errorf("option %q carries the disclosure but does not escalate", option.Name)
+			}
+			continue
+		}
+		found++
+		if !strings.Contains(option.Name, "outside the sandbox") {
+			t.Errorf("prefix option %q does not say the command leaves the sandbox", option.Name)
+		}
+	}
+	if found != 2 {
+		t.Fatalf("expected both prefix options, saw %d", found)
+	}
+}
+
+func TestACPPrefixOptionsStaySilentWithoutEscalation(t *testing.T) {
+	for _, option := range buildPermissionOptions(escalationRequest(false)) {
+		if strings.Contains(option.Name, "sandbox") {
+			t.Errorf("option %q warns about the sandbox when approving would not leave it", option.Name)
+		}
+	}
+}
+
+// The disclosure must live in the label only. The option id is the decision
+// action round-tripped verbatim, and decisionFromOutcome matches it against
+// what was offered, so decorating it would fail every prefix approval closed.
+func TestACPDisclosureDoesNotDisturbTheOptionIDRoundTrip(t *testing.T) {
+	request := escalationRequest(true)
+	for _, option := range buildPermissionOptions(request) {
+		decision := decisionFromOutcome(
+			RequestPermissionOutcome{Outcome: OutcomeSelected, OptionID: option.OptionID},
+			request.AvailableDecisions,
+		)
+		if string(decision.Action) != option.OptionID {
+			t.Errorf("option id %q round-tripped to %q (%s)", option.OptionID, decision.Action, decision.Reason)
+		}
+	}
+}

internal/agent/compaction.go

@@ -38,8 +38,9 @@ const compactionTriggerRatio = 0.7
 // transcript (and so tests can assert on it).
 const summaryLabel = "[Summary of earlier conversation]"
 
-// summaryInstructions is the system prompt handed to the summarizer model.
-const summaryInstructions = "You are compacting a coding-assistant conversation to save context. " +
+// CompactionSummaryInstructions is the system prompt handed to both automatic
+// and manually requested compaction summarizers.
+const CompactionSummaryInstructions = "You are compacting a coding-assistant conversation to save context. " +
 	"Write a dense, factual summary of the conversation so far. Preserve: the user's goals and explicit constraints; " +
 	"decisions made and why; files created or modified (with paths) and key code changes; commands run and their important " +
 	"results; and anything still in progress or unresolved. Omit pleasantries. Use terse bullet points. Do not invent details. " +
@@ -75,6 +76,12 @@ type CompactionResult struct {
 	// summary message also includes summaryLabel and any preserved structured
 	// state needed by later compactions.
 	SummaryText string
+	// ProjectedChars is the text content sent to the summarizer after semantic
+	// projection, excluding provider protocol framing.
+	ProjectedChars int
+	// Truncated reports whether projection dropped content to satisfy its
+	// bounded brief or previous-summary limits.
+	Truncated bool
 	// Compacted reports whether Messages contains an injected summary.
 	Compacted bool
 }
@@ -216,11 +223,11 @@ func CompactMessages(messages []zeroruntime.Message, opts CompactionOptions) (Co
 		}, nil
 	}
 
-	summary, err := opts.Summarize(middle)
+	summaryResult, err := SummarizeCompactionMessages(middle, opts.Summarize)
 	if err != nil {
 		return CompactionResult{}, err
 	}
-	summary = strings.TrimSpace(summary)
+	summary := summaryResult.SummaryText
 
 	// Preserve structured state (active plan + loaded skills) from the elided
 	// middle verbatim, so it is not lost or paraphrased away by the prose summary.
@@ -238,10 +245,53 @@ func CompactMessages(messages []zeroruntime.Message, opts CompactionOptions) (Co
 		RemovedCount:   len(middle),
 		PreservedCount: len(messages) - len(middle),
 		SummaryText:    summary,
+		ProjectedChars: summaryResult.ProjectedChars,
+		Truncated:      summaryResult.Truncated,
 		Compacted:      true,
 	}, nil
 }
 
+// CompactionSummaryResult describes the shared summarization input and output.
+type CompactionSummaryResult struct {
+	SummaryText    string
+	ProjectedChars int
+	Truncated      bool
+}
+
+// SummarizeCompactionMessages applies the shared semantic projection before
+// invoking a caller-supplied summarizer. Automatic context-pressure compaction
+// and manual session compaction both use this path.
+func SummarizeCompactionMessages(messages []zeroruntime.Message, summarize func([]zeroruntime.Message) (string, error)) (CompactionSummaryResult, error) {
+	if summarize == nil {
+		return CompactionSummaryResult{}, errors.New("compaction requires a Summarize function")
+	}
+	projection := projectCompactionInput(messages)
+	summaryInput := projection.messages
+	if len(summaryInput) == 0 {
+		summaryInput = messages
+	}
+	summary, err := summarize(summaryInput)
+	if err != nil {
+		return CompactionSummaryResult{}, err
+	}
+	return CompactionSummaryResult{
+		SummaryText:    strings.TrimSpace(summary),
+		ProjectedChars: compactionMessageChars(summaryInput),
+		Truncated:      projection.truncated,
+	}, nil
+}
+
+func compactionMessageChars(messages []zeroruntime.Message) int {
+	total := 0
+	for _, message := range messages {
+		total += len(message.Content)
+		for _, call := range message.ToolCalls {
+			total += len(call.Name) + len(call.Arguments)
+		}
+	}
+	return total
+}
+
 // safeSuffixBoundary walks the preserve boundary backward (toward systemEnd) so
 // the preserved suffix begins on a user or assistant message rather than a
 // tool/tool_result message. A tool result with no preceding assistant tool call
@@ -331,6 +381,8 @@ type compactionState struct {
 	// but its token COST must still be counted so usage reports and budgets include it.
 	onUsage func(Usage)
 	task    *taskState
+	planner *contextPlanner
+	trace   *trace.Recorder
 
 	// calibrationRatio scales the raw byte/4 token estimate toward the provider's
 	// real prompt-token count. ApproxTextTokens over-counts code-heavy content by
@@ -377,6 +429,8 @@ func newCompactionState(options Options, task *taskState) *compactionState {
 		preserveLast: options.CompactionPreserveLast,
 		onUsage:      options.OnUsage,
 		task:         task,
+		planner:      newContextPlanner(contextPlannerConfig{contextWindow: options.ContextWindow}),
+		trace:        options.Trace,
 	}
 	return state
 }
@@ -432,7 +486,7 @@ func (state *compactionState) maybeCompact(
 
 	compacted, err := Compact(messages, CompactionOptions{
 		PreserveLast: state.preserveLast,
-		Summarize:    summarizeClosure(ctx, provider, state.onUsage),
+		Summarize:    state.summarizeClosure(ctx, provider),
 		taskState:    state.task.snapshotForCompaction(messages),
 	})
 	if err != nil {
@@ -483,7 +537,7 @@ func (state *compactionState) recover(
 
 	result, compactErr := Compact(messages, CompactionOptions{
 		PreserveLast: state.preserveLast,
-		Summarize:    summarizeClosure(ctx, provider, state.onUsage),
+		Summarize:    state.summarizeClosure(ctx, provider),
 		taskState:    state.task.snapshotForCompaction(messages),
 	})
 	if compactErr != nil {
@@ -517,9 +571,12 @@ func (state *compactionState) recover(
 // provider call. The summary stream intentionally does NOT forward OnText (so
 // compaction stays invisible on the user-facing surface), but it DOES forward
 // OnUsage so the summarizer's token cost is still counted by usage/budgeting.
-func summarizeClosure(ctx context.Context, provider Provider, onUsage func(Usage)) func([]zeroruntime.Message) (string, error) {
+func (state *compactionState) summarizeClosure(ctx context.Context, provider Provider) func([]zeroruntime.Message) (string, error) {
+	if state.planner == nil {
+		state.planner = newContextPlanner(contextPlannerConfig{})
+	}
 	return func(toSummarize []zeroruntime.Message) (string, error) {
-		return summarizeWithFallback(ctx, provider, toSummarize, onUsage)
+		return summarizeWithPlanner(ctx, provider, toSummarize, state.onUsage, state.planner, state.trace)
 	}
 }
 
@@ -531,7 +588,11 @@ func summarizeClosure(ctx context.Context, provider Provider, onUsage func(Usage
 // Non-context-limit errors (and a single message that still won't fit) surface
 // to the caller unchanged.
 func summarizeWithFallback(ctx context.Context, provider Provider, messages []zeroruntime.Message, onUsage func(Usage)) (string, error) {
-	summary, err := summarizeMessagesOnce(ctx, provider, messages, onUsage)
+	return summarizeWithPlanner(ctx, provider, messages, onUsage, newContextPlanner(contextPlannerConfig{}), nil)
+}
+
+func summarizeWithPlanner(ctx context.Context, provider Provider, messages []zeroruntime.Message, onUsage func(Usage), planner *contextPlanner, recorder *trace.Recorder) (string, error) {
+	summary, err := summarizeMessagesOnce(ctx, provider, messages, onUsage, planner, recorder)
 	if err == nil {
 		return summary, nil
 	}
@@ -540,11 +601,11 @@ func summarizeWithFallback(ctx context.Context, provider Provider, messages []ze
 	}
 
 	mid := len(messages) / 2
-	left, leftErr := summarizeWithFallback(ctx, provider, messages[:mid], onUsage)
+	left, leftErr := summarizeWithPlanner(ctx, provider, messages[:mid], onUsage, planner, recorder)
 	if leftErr != nil {
 		return "", leftErr
 	}
-	right, rightErr := summarizeWithFallback(ctx, provider, messages[mid:], onUsage)
+	right, rightErr := summarizeWithPlanner(ctx, provider, messages[mid:], onUsage, planner, recorder)
 	if rightErr != nil {
 		return "", rightErr
 	}
@@ -557,7 +618,7 @@ func summarizeWithFallback(ctx context.Context, provider Provider, messages []ze
 	combined := strings.TrimSpace(left + "\n\n" + right)
 	reduced, reduceErr := summarizeMessagesOnce(ctx, provider, []zeroruntime.Message{
 		{Role: zeroruntime.MessageRoleUser, Content: combined},
-	}, onUsage)
+	}, onUsage, planner, recorder)
 	if reduceErr != nil {
 		if isContextLimitError(reduceErr.Error()) {
 			// Even the two combined partials don't fit (extreme): fall back to the
@@ -573,15 +634,15 @@ func summarizeWithFallback(ctx context.Context, provider Provider, messages []ze
 }
 
 // summarizeMessagesOnce performs a single tool-less summarization call.
-func summarizeMessagesOnce(ctx context.Context, provider Provider, messages []zeroruntime.Message, onUsage func(Usage)) (string, error) {
-	request := zeroruntime.CompletionRequest{
-		Messages: []zeroruntime.Message{
-			{Role: zeroruntime.MessageRoleSystem, Content: summaryInstructions},
-			{Role: zeroruntime.MessageRoleUser, Content: "Summarize this conversation:\n\n" + renderTranscript(messages)},
-		},
-		// No tools: this is a plain text summarization call.
+func summarizeMessagesOnce(ctx context.Context, provider Provider, messages []zeroruntime.Message, onUsage func(Usage), planner *contextPlanner, recorder *trace.Recorder) (string, error) {
+	requestMessages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleSystem, Content: CompactionSummaryInstructions},
+		{Role: zeroruntime.MessageRoleUser, Content: "Summarize this conversation:\n\n" + renderTranscript(messages)},
 	}
-	stream, err := provider.StreamCompletion(ctx, request)
+	parts := systemPromptParts{prompt: CompactionSummaryInstructions, baseInstructions: CompactionSummaryInstructions}
+	plan := planner.planWithPromptParts(requestMessages, nil, "", parts)
+	recordContextPlanTrace(recorder, plan)
+	stream, err := provider.StreamCompletion(ctx, plan.Request)
 	if err != nil {
 		return "", err
 	}

internal/agent/compaction_metadata_test.go

@@ -43,8 +43,14 @@ func TestCompactMessagesReturnsMetadataForManualCompaction(t *testing.T) {
 	if result.SummaryText != "manual summary" {
 		t.Fatalf("SummaryText = %q, want trimmed summary", result.SummaryText)
 	}
-	if len(captured) != 3 || captured[0].Content != "first question" || captured[2].Content != "second question" {
-		t.Fatalf("summarized middle = %#v, want the three non-preserved non-system messages", captured)
+	if result.ProjectedChars != compactionMessageChars(captured) || result.ProjectedChars == 0 {
+		t.Fatalf("ProjectedChars = %d, want %d", result.ProjectedChars, compactionMessageChars(captured))
+	}
+	if result.Truncated {
+		t.Fatal("Truncated = true for a projection within its limits")
+	}
+	if len(captured) != 1 || !strings.Contains(captured[0].Content, "first question") || !strings.Contains(captured[0].Content, "second question") {
+		t.Fatalf("summarized projection = %#v, want intent from the non-preserved middle", captured)
 	}
 	if len(result.Messages) != 4 {
 		t.Fatalf("compacted message count = %d, want 4", len(result.Messages))
@@ -96,11 +102,46 @@ func TestCompactMessagesNoopReturnsUncompactedMetadata(t *testing.T) {
 	if result.SummaryText != "" {
 		t.Fatalf("SummaryText = %q, want empty", result.SummaryText)
 	}
+	if result.ProjectedChars != 0 || result.Truncated {
+		t.Fatalf("no-op projection metadata = (%d, %t), want zero values", result.ProjectedChars, result.Truncated)
+	}
 	if !reflect.DeepEqual(result.Messages, messages) {
 		t.Fatalf("Messages changed on no-op: %#v", result.Messages)
 	}
 }
 
+func TestCompactMessagesReturnsTruncatedProjectionMetadata(t *testing.T) {
+	messages := []zeroruntime.Message{{Role: zeroruntime.MessageRoleSystem, Content: "system"}}
+	for index := range 20 {
+		messages = append(messages, zeroruntime.Message{
+			Role:    zeroruntime.MessageRoleUser,
+			Content: strings.Repeat("contextword ", 256) + string(rune('a'+index)),
+		})
+	}
+	messages = append(messages,
+		zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, Content: "recent answer"},
+		zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "latest question"},
+	)
+
+	var captured []zeroruntime.Message
+	result, err := CompactMessages(messages, CompactionOptions{
+		PreserveLast: 2,
+		Summarize: func(toSummarize []zeroruntime.Message) (string, error) {
+			captured = append([]zeroruntime.Message(nil), toSummarize...)
+			return "bounded summary", nil
+		},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if !result.Compacted || !result.Truncated {
+		t.Fatalf("compaction metadata = compacted %t, truncated %t; want both true", result.Compacted, result.Truncated)
+	}
+	if result.ProjectedChars != compactionMessageChars(captured) || result.ProjectedChars == 0 {
+		t.Fatalf("ProjectedChars = %d, want %d", result.ProjectedChars, compactionMessageChars(captured))
+	}
+}
+
 func TestCompactMessagesPropagatesSummarizeError(t *testing.T) {
 	messages := []zeroruntime.Message{
 		{Role: zeroruntime.MessageRoleSystem, Content: "system"},

internal/agent/compaction_preserve.go

@@ -102,7 +102,7 @@ type skillEntry struct {
 	body string
 }
 
-// recentEdits returns the files mutated by write_file/edit_file calls in messages
+// recentEdits returns files mutated by editing calls in messages
 // — latest note per path, in last-seen order — as skillEntry{name: path, body:
 // note}. After compaction elides the editing turns, this tells the model WHAT it
 // changed in each file (from the tool's result) so it need not re-read to
@@ -113,6 +113,7 @@ type skillEntry struct {
 // rather than an earlier, now-stale entry.
 func recentEdits(messages []zeroruntime.Message) []skillEntry {
 	pathByID := map[string]string{}
+	noteByPath := map[string]string{}
 	sequence := make([]string, 0)
 	for _, message := range messages {
 		for _, call := range message.ToolCalls {
@@ -129,12 +130,24 @@ func recentEdits(messages []zeroruntime.Message) []skillEntry {
 			sequence = append(sequence, path)
 		}
 	}
+	for _, message := range messages {
+		if message.Role != zeroruntime.MessageRoleTool || len(message.ChangedFiles) == 0 {
+			continue
+		}
+		for _, path := range message.ChangedFiles {
+			path = strings.TrimSpace(path)
+			if path == "" {
+				continue
+			}
+			sequence = append(sequence, path)
+			noteByPath[path] = editNote(message.Content)
+		}
+	}
 	order := lastSeenOrder(sequence)
 	if len(order) == 0 {
 		return nil
 	}
 
-	noteByPath := map[string]string{}
 	for _, message := range messages {
 		if message.Role != zeroruntime.MessageRoleTool || message.ToolCallID == "" {
 			continue
@@ -425,15 +438,20 @@ type preservedState struct {
 }
 
 type preservedTaskState struct {
-	Objective           string     `json:"objective"`
-	Status              taskStatus `json:"status,omitempty"`
-	Pending             int        `json:"pending,omitempty"`
-	InProgress          int        `json:"in_progress,omitempty"`
-	Completed           int        `json:"completed,omitempty"`
-	Failed              int        `json:"failed,omitempty"`
-	VerificationPassed  int        `json:"verification_passed,omitempty"`
-	VerificationFailed  int        `json:"verification_failed,omitempty"`
-	VerificationOutcome Outcome    `json:"verification_outcome,omitempty"`
+	Objective           string              `json:"objective"`
+	Status              taskStatus          `json:"status,omitempty"`
+	Pending             int                 `json:"pending,omitempty"`
+	InProgress          int                 `json:"in_progress,omitempty"`
+	Completed           int                 `json:"completed,omitempty"`
+	Failed              int                 `json:"failed,omitempty"`
+	VerificationPassed  int                 `json:"verification_passed,omitempty"`
+	VerificationFailed  int                 `json:"verification_failed,omitempty"`
+	VerificationOutcome Outcome             `json:"verification_outcome,omitempty"`
+	Constraints         []string            `json:"constraints,omitempty"`
+	ChangedFiles        []string            `json:"changed_files,omitempty"`
+	UnresolvedFailures  []taskFailureState  `json:"unresolved_failures,omitempty"`
+	Approvals           []taskApprovalState `json:"approvals,omitempty"`
+	Artifacts           []taskArtifactState `json:"artifacts,omitempty"`
 }
 
 type preservedEdit struct {
@@ -468,7 +486,12 @@ func appendPreservedState(summary string, middle []zeroruntime.Message, taskSnap
 	task := priorState.Task
 	if taskSnapshot != nil {
 		task = &preservedTaskState{
-			Objective: capTaskObjective(taskSnapshot.Objective),
+			Objective:          capTaskObjective(taskSnapshot.Objective),
+			Constraints:        mergeBoundedComparable(priorTaskConstraints(priorState.Task), taskSnapshot.Constraints, maxTaskConstraints),
+			ChangedFiles:       mergeBoundedComparable(priorTaskChangedFiles(priorState.Task), taskSnapshot.ChangedFiles, maxTaskEvidenceEntries),
+			UnresolvedFailures: mergeTaskFailures(priorTaskFailures(priorState.Task), taskSnapshot.UnresolvedFailures, taskSnapshot.ResolvedFailureKeys),
+			Approvals:          mergeBoundedComparable(priorTaskApprovals(priorState.Task), taskSnapshot.Approvals, maxTaskEvidenceEntries),
+			Artifacts:          mergeBoundedComparable(priorTaskArtifacts(priorState.Task), taskSnapshot.Artifacts, maxTaskEvidenceEntries),
 		}
 		// Plan parity corroborates only the mutable task projection. The objective
 		// comes directly from the run prompt and is immutable, so it must survive
@@ -484,6 +507,13 @@ func appendPreservedState(summary string, middle []zeroruntime.Message, taskSnap
 			task.VerificationOutcome = taskSnapshot.Verification.LastOutcome
 		}
 	}
+	freshConstraints := explicitConstraintsFromMessages(middle)
+	if len(freshConstraints) > 0 {
+		if task == nil {
+			task = &preservedTaskState{}
+		}
+		task.Constraints = mergeBoundedComparable(task.Constraints, freshConstraints, maxTaskConstraints)
+	}
 
 	// Plan: a fresh update_plan in middle is authoritative; otherwise carry the
 	// plan preserved by an earlier compaction.
@@ -517,6 +547,95 @@ func appendPreservedState(summary string, middle []zeroruntime.Message, taskSnap
 	return summary
 }
 
+func explicitConstraintsFromMessages(messages []zeroruntime.Message) []string {
+	var constraints []string
+	for _, message := range messages {
+		if message.Role != zeroruntime.MessageRoleUser || strings.Contains(message.Content, preservedStateLabel) {
+			continue
+		}
+		if _, body := projectInstructionBlock(message.Content); body != "" {
+			continue
+		}
+		constraints = mergeBoundedComparable(constraints, extractExplicitConstraints(message.Content), maxTaskConstraints)
+	}
+	return constraints
+}
+
+func priorTaskConstraints(task *preservedTaskState) []string {
+	if task == nil {
+		return nil
+	}
+	return task.Constraints
+}
+
+func priorTaskChangedFiles(task *preservedTaskState) []string {
+	if task == nil {
+		return nil
+	}
+	return task.ChangedFiles
+}
+
+func priorTaskFailures(task *preservedTaskState) []taskFailureState {
+	if task == nil {
+		return nil
+	}
+	return task.UnresolvedFailures
+}
+
+func priorTaskApprovals(task *preservedTaskState) []taskApprovalState {
+	if task == nil {
+		return nil
+	}
+	return task.Approvals
+}
+
+func priorTaskArtifacts(task *preservedTaskState) []taskArtifactState {
+	if task == nil {
+		return nil
+	}
+	return task.Artifacts
+}
+
+func mergeTaskFailures(older, newer []taskFailureState, resolved []string) []taskFailureState {
+	resolvedSet := make(map[string]struct{}, len(resolved))
+	for _, key := range resolved {
+		resolvedSet[key] = struct{}{}
+	}
+	merged := make([]taskFailureState, 0, len(older)+len(newer))
+	for _, failure := range append(append([]taskFailureState(nil), older...), newer...) {
+		if _, ok := resolvedSet[failure.Key]; ok {
+			continue
+		}
+		withoutSameKey := make([]taskFailureState, 0, len(merged))
+		for _, existing := range merged {
+			if existing.Key != failure.Key {
+				withoutSameKey = append(withoutSameKey, existing)
+			}
+		}
+		merged = append(withoutSameKey, failure)
+	}
+	if len(merged) > maxTaskEvidenceEntries {
+		merged = merged[len(merged)-maxTaskEvidenceEntries:]
+	}
+	return merged
+}
+
+func mergeBoundedComparable[T comparable](older, newer []T, limit int) []T {
+	merged := make([]T, 0, len(older)+len(newer))
+	seen := make(map[T]struct{}, len(older)+len(newer))
+	for _, value := range append(append([]T(nil), older...), newer...) {
+		if _, ok := seen[value]; ok {
+			continue
+		}
+		seen[value] = struct{}{}
+		merged = append(merged, value)
+	}
+	if len(merged) > limit {
+		merged = merged[len(merged)-limit:]
+	}
+	return merged
+}
+
 func capTaskObjective(objective string) string {
 	objective = strings.TrimSpace(objective)
 	if len(objective) <= maxTaskObjectiveBytes {

internal/agent/compaction_preserve_test.go

@@ -6,6 +6,7 @@ import (
 	"testing"
 	"unicode/utf8"
 
+	"github.com/Gitlawb/zero/internal/tools"
 	"github.com/Gitlawb/zero/internal/zeroruntime"
 )
 
@@ -64,6 +65,9 @@ func TestCompactPreservesBoundedTaskContext(t *testing.T) {
 	objective := strings.Repeat("世", maxTaskObjectiveBytes)
 	task := newTaskState(objective, nil)
 	task.observe(taskStateEvent{kind: taskStateEventPlan, arguments: `{"plan":[{"content":"write code","status":"in_progress"},{"content":"add tests","status":"pending"}]}`})
+	task.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"patch":"*** Update File: internal/db.go"}`, toolResult: ToolResult{
+		Name: "apply_patch", Status: tools.StatusOK, Output: "Done!", ChangedFiles: []string{"internal/db.go"},
+	}})
 	messages := stateConversation()
 	compacted, err := Compact(messages, CompactionOptions{
 		PreserveLast: 2,
@@ -80,6 +84,69 @@ func TestCompactPreservesBoundedTaskContext(t *testing.T) {
 	if len(state.Task.Objective) > maxTaskObjectiveBytes || !utf8.ValidString(state.Task.Objective) {
 		t.Fatalf("objective was not safely bounded: %d bytes %q", len(state.Task.Objective), state.Task.Objective)
 	}
+	if len(state.Task.ChangedFiles) != 1 || state.Task.ChangedFiles[0] != "internal/db.go" {
+		t.Fatalf("changed files were not preserved: %#v", state.Task.ChangedFiles)
+	}
+}
+
+func TestCompactPreservesRuntimeEvidenceAcrossRepeatedCompaction(t *testing.T) {
+	task := newTaskState("Please keep the change focused.", nil)
+	task.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"cmd":"go test ./..."}`, toolResult: ToolResult{
+		Name: "exec_command", Status: tools.StatusError, Output: "Error: tests failed",
+		Meta: map[string]string{"spill_path": ".zero/artifacts/tests.txt"},
+	}})
+	task.observe(taskStateEvent{kind: taskStateEventPermission, permission: PermissionEvent{
+		ToolName: "exec_command", DecisionAction: PermissionDecisionAllowForSession, Scope: "/tmp",
+	}})
+	messages := stateConversation()
+
+	first, err := Compact(messages, CompactionOptions{
+		PreserveLast: 2,
+		Summarize:    func([]zeroruntime.Message) (string, error) { return "FIRST", nil },
+		taskState:    task.snapshotForCompaction(messages),
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	task.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"cmd":"go test ./..."}`, toolResult: ToolResult{
+		Name: "exec_command", Status: tools.StatusError, Output: "Error: tests still fail with newer evidence",
+		Meta: map[string]string{"spill_path": ".zero/artifacts/tests.txt"},
+	}})
+	secondInput := append(append([]zeroruntime.Message{}, first...),
+		zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "Never add background memory models."},
+		zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, Content: "understood"},
+		zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "continue"},
+		zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, Content: "working"},
+	)
+	second, err := Compact(secondInput, CompactionOptions{
+		PreserveLast: 2,
+		Summarize:    func([]zeroruntime.Message) (string, error) { return "SECOND", nil },
+		taskState:    task.snapshotForCompaction(secondInput),
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	state := parsePreservedStateBlock(second[1].Content)
+	if state.Task == nil || len(state.Task.UnresolvedFailures) != 1 || len(state.Task.Approvals) != 1 || len(state.Task.Artifacts) != 1 {
+		t.Fatalf("runtime evidence did not survive repeated compaction: %#v", state.Task)
+	}
+	if got := state.Task.UnresolvedFailures[0].Summary; got != "Error: tests still fail with newer evidence" {
+		t.Fatalf("newer failure evidence did not replace the older summary: %#v", state.Task.UnresolvedFailures)
+	}
+	for _, want := range []string{"Please keep the change focused.", "Never add background memory models."} {
+		if !containsString(state.Task.Constraints, want) {
+			t.Fatalf("constraint %q missing after repeated compaction: %#v", want, state.Task.Constraints)
+		}
+	}
+}
+
+func containsString(values []string, want string) bool {
+	for _, value := range values {
+		if value == want {
+			return true
+		}
+	}
+	return false
 }
 
 func TestCompactPreservesObjectiveAfterPlanParityMismatch(t *testing.T) {

internal/agent/compaction_projection.go

@@ -0,0 +1,315 @@
+package agent
+
+import (
+	"encoding/json"
+	"fmt"
+	"regexp"
+	"strings"
+
+	"github.com/Gitlawb/zero/internal/zeroruntime"
+)
+
+const (
+	compactionUserWordBudget       = 256
+	compactionAssistantWordBudget  = 200
+	compactionToolCallsPerTurn     = 8
+	compactionToolArgumentBytes    = 120
+	compactionErrorBytes           = 150
+	compactionResultBytes          = 1200
+	compactionPreviousSummaryBytes = 16 * 1024
+	compactionBriefMaxBytes        = 24 * 1024
+)
+
+var compactionWordPattern = regexp.MustCompile(`[\p{L}\p{N}]+`)
+
+type compactionProjection struct {
+	messages  []zeroruntime.Message
+	truncated bool
+}
+
+// projectCompactionInput removes reconstructible tool output before the model
+// summary call. It retains a bounded transcript of user intent, assistant
+// decisions, tool actions, and concise errors. Exact durable state is appended
+// separately from the original messages after the summary returns.
+func projectCompactionInput(messages []zeroruntime.Message) compactionProjection {
+	sections := make([]string, 0, len(messages))
+	previousSummary := ""
+	truncated := false
+	for index, message := range messages {
+		switch message.Role {
+		case zeroruntime.MessageRoleUser:
+			content := message.Content
+			if marker := strings.Index(content, preservedStateLabel); marker >= 0 {
+				content = content[:marker]
+			}
+			trimmed := strings.TrimSpace(content)
+			if strings.HasPrefix(trimmed, summaryLabel) {
+				fullSummary := strings.TrimSpace(strings.TrimPrefix(trimmed, summaryLabel))
+				previousSummary = clipHeadTailBytes(fullSummary, compactionPreviousSummaryBytes)
+				truncated = truncated || len(fullSummary) > compactionPreviousSummaryBytes
+				continue
+			}
+			if content = clipInformativeWords(content, compactionUserWordBudget); content != "" {
+				sections = append(sections, fmt.Sprintf("[user #%d]\n%s", index, content))
+			}
+		case zeroruntime.MessageRoleAssistant:
+			lines := make([]string, 0, 1+len(message.ToolCalls))
+			if content := clipInformativeWords(message.Content, compactionAssistantWordBudget); content != "" {
+				lines = append(lines, content)
+			}
+			calls := message.ToolCalls
+			omitted := 0
+			if len(calls) > compactionToolCallsPerTurn {
+				omitted = len(calls) - compactionToolCallsPerTurn
+				calls = calls[omitted:]
+			}
+			if omitted > 0 {
+				lines = append(lines, fmt.Sprintf("* (%d earlier tool calls omitted)", omitted))
+			}
+			for _, call := range calls {
+				lines = append(lines, compactionToolCallLine(call))
+			}
+			if len(lines) > 0 {
+				sections = append(sections, fmt.Sprintf("[assistant #%d]\n%s", index, strings.Join(lines, "\n")))
+			}
+		case zeroruntime.MessageRoleTool:
+			// New tool-result messages carry the execution status directly, as the
+			// source ToolResult does. Keep the text check for older session history
+			// created before Message exposed IsError.
+			name := toolNameForResult(messages, index)
+			mustPreserve := name == "ask_user" || len(message.ChangedFiles) > 0
+			if !mustPreserve && !message.IsError && !isLikelyToolError(message.Content) {
+				continue
+			}
+			if name == "" {
+				name = "tool"
+			}
+			switch {
+			case message.IsError || isLikelyToolError(message.Content):
+				sections = append(sections, fmt.Sprintf("[tool_error #%d] %s\n%s", index, name, clipBytes(firstLine(message.Content), compactionErrorBytes)))
+			case name == "ask_user":
+				sections = append(sections, fmt.Sprintf("[user_answer #%d] %s\n%s", index, name, clipBytes(message.Content, compactionResultBytes)))
+			default:
+				sections = append(sections, fmt.Sprintf("[tool_result #%d] %s changed %s\n%s", index, name,
+					clipBytes(strings.Join(message.ChangedFiles, ", "), compactionToolArgumentBytes), clipBytes(firstLine(message.Content), compactionErrorBytes)))
+			}
+		}
+	}
+	if len(sections) == 0 && previousSummary == "" {
+		return compactionProjection{}
+	}
+	brief, briefTruncated := capCompactionBrief(strings.Join(sections, "\n\n"))
+	truncated = truncated || briefTruncated
+	if previousSummary != "" {
+		brief = "[previous summary]\n" + previousSummary + "\n\n" + brief
+	}
+	return compactionProjection{
+		messages:  []zeroruntime.Message{{Role: zeroruntime.MessageRoleUser, Content: strings.TrimSpace(brief)}},
+		truncated: truncated,
+	}
+}
+
+func capCompactionBrief(brief string) (string, bool) {
+	if len(brief) <= compactionBriefMaxBytes {
+		return brief, false
+	}
+	marker := "\n\n...[middle transcript omitted to fit compaction budget]...\n\n"
+	available := compactionBriefMaxBytes - len(marker)
+	// Keep both chronological edges: the oldest material has not necessarily
+	// been summarized before, while the newest material is most actionable.
+	headBytes := available * 2 / 5
+	tailBytes := available - headBytes
+	head := clipPrefixAtBoundary(brief, headBytes)
+	tail := clipSuffixAtBoundary(brief, tailBytes)
+	return strings.TrimSpace(head) + marker + strings.TrimSpace(tail), true
+}
+
+func compactionToolCallLine(call zeroruntime.ToolCall) string {
+	detail := ""
+	var arguments map[string]any
+	if json.Unmarshal([]byte(strings.TrimSpace(call.Arguments)), &arguments) == nil {
+		for _, key := range []string{"file_path", "path", "url", "query", "pattern", "prompt", "description", "question"} {
+			if value, ok := arguments[key].(string); ok && strings.TrimSpace(value) != "" {
+				detail = value
+				break
+			}
+		}
+		if detail == "" && call.Name == "ask_user" {
+			detail = askUserQuestionsDetail(arguments)
+		}
+		if detail == "" && call.Name == "apply_patch" {
+			if patch, ok := arguments["patch"].(string); ok {
+				detail = strings.Join(patchPaths(patch), ", ")
+			}
+		}
+	}
+	if detail == "" {
+		detail = commandFromArguments(call.Arguments)
+	}
+	if detail == "" {
+		return "* " + call.Name
+	}
+	return fmt.Sprintf("* %s %q", call.Name, clipBytes(detail, compactionToolArgumentBytes))
+}
+
+func isLikelyToolError(content string) bool {
+	prefix := strings.TrimSpace(content)
+	if len(prefix) > compactionErrorBytes {
+		prefix = prefix[:compactionErrorBytes]
+	}
+	lower := strings.ToLower(prefix)
+	for _, prefix := range []string{"error:", "tool error:", "failed:", "permission denied", "command failed"} {
+		if strings.HasPrefix(lower, prefix) {
+			return true
+		}
+	}
+	return false
+}
+
+func clipInformativeWords(text string, limit int) string {
+	flat := strings.Join(strings.Fields(text), " ")
+	if flat == "" || limit <= 0 {
+		return ""
+	}
+	count := 0
+	for _, location := range compactionWordPattern.FindAllStringIndex(flat, -1) {
+		word := strings.ToLower(flat[location[0]:location[1]])
+		if compactionStopWords[word] {
+			continue
+		}
+		count++
+		if count > limit {
+			end := location[0]
+			return strings.TrimSpace(flat[:end]) + "...(truncated)"
+		}
+	}
+	return flat
+}
+
+func clipBytes(text string, limit int) string {
+	text = strings.TrimSpace(text)
+	if limit <= 0 {
+		return ""
+	}
+	if len(text) <= limit {
+		return text
+	}
+	if limit <= 3 {
+		end := limit
+		for end > 0 && end < len(text) && text[end]&0xc0 == 0x80 {
+			end--
+		}
+		return text[:end]
+	}
+	end := limit - 3
+	for end > 0 && end < len(text) && text[end]&0xc0 == 0x80 {
+		end--
+	}
+	return strings.TrimSpace(text[:end]) + "..."
+}
+
+func clipHeadTailBytes(text string, limit int) string {
+	text = strings.TrimSpace(text)
+	if len(text) <= limit {
+		return text
+	}
+	if limit <= 0 {
+		return ""
+	}
+	marker := "\n...[middle omitted]...\n"
+	if limit <= len(marker) {
+		return clipBytes(text, limit)
+	}
+	available := limit - len(marker)
+	head := clipPrefixAtBoundary(text, available/2)
+	tail := clipSuffixAtBoundary(text, available-available/2)
+	return strings.TrimSpace(head) + marker + strings.TrimSpace(tail)
+}
+
+func clipPrefixAtBoundary(text string, limit int) string {
+	if limit <= 0 {
+		return ""
+	}
+	if len(text) <= limit {
+		return text
+	}
+	end := limit
+	for end > 0 && text[end]&0xc0 == 0x80 {
+		end--
+	}
+	if boundary := strings.LastIndex(text[:end], "\n\n["); boundary > 0 {
+		end = boundary
+	}
+	return text[:end]
+}
+
+func clipSuffixAtBoundary(text string, limit int) string {
+	if limit <= 0 {
+		return ""
+	}
+	if len(text) <= limit {
+		return text
+	}
+	start := len(text) - limit
+	for start < len(text) && text[start]&0xc0 == 0x80 {
+		start++
+	}
+	if boundary := strings.Index(text[start:], "\n\n["); boundary >= 0 {
+		start += boundary + 2
+	}
+	return text[start:]
+}
+
+func askUserQuestionsDetail(arguments map[string]any) string {
+	raw, ok := arguments["questions"].([]any)
+	if !ok {
+		return ""
+	}
+	questions := make([]string, 0, len(raw))
+	for _, item := range raw {
+		object, ok := item.(map[string]any)
+		if !ok {
+			continue
+		}
+		if question, ok := object["question"].(string); ok && strings.TrimSpace(question) != "" {
+			questions = append(questions, strings.TrimSpace(question))
+		}
+	}
+	return strings.Join(questions, " | ")
+}
+
+func patchPaths(patch string) []string {
+	var paths []string
+	seen := map[string]bool{}
+	for _, line := range strings.Split(patch, "\n") {
+		for _, prefix := range []string{"*** Add File: ", "*** Update File: ", "*** Delete File: ", "*** Move to: "} {
+			if !strings.HasPrefix(line, prefix) {
+				continue
+			}
+			path := strings.TrimSpace(strings.TrimPrefix(line, prefix))
+			if path != "" && !seen[path] {
+				seen[path] = true
+				paths = append(paths, path)
+			}
+		}
+	}
+	return paths
+}
+
+var compactionStopWords = map[string]bool{
+	"a": true, "an": true, "the": true, "is": true, "are": true, "was": true, "were": true,
+	"be": true, "been": true, "being": true, "have": true, "has": true, "had": true,
+	"do": true, "does": true, "did": true, "will": true, "would": true, "could": true,
+	"should": true, "may": true, "might": true, "shall": true, "can": true, "need": true, "must": true,
+	"to": true, "of": true, "in": true, "for": true, "on": true, "with": true, "at": true,
+	"by": true, "from": true, "as": true, "into": true, "through": true, "during": true,
+	"before": true, "after": true, "above": true, "below": true, "between": true, "under": true, "over": true,
+	"and": true, "but": true, "or": true, "nor": true, "not": true, "so": true, "yet": true,
+	"both": true, "either": true, "neither": true, "each": true, "every": true, "all": true,
+	"any": true, "few": true, "more": true, "most": true, "other": true, "some": true, "such": true, "no": true,
+	"that": true, "this": true, "these": true, "those": true, "it": true, "its": true,
+	"i": true, "me": true, "my": true, "we": true, "our": true, "you": true, "your": true,
+	"he": true, "him": true, "his": true, "she": true, "her": true, "they": true, "them": true, "their": true,
+	"who": true, "which": true, "what": true, "if": true, "then": true, "than": true,
+	"when": true, "where": true, "how": true, "just": true, "also": true,
+}

internal/agent/compaction_projection_test.go

@@ -0,0 +1,130 @@
+package agent
+
+import (
+	"strings"
+	"testing"
+	"unicode/utf8"
+
+	"github.com/Gitlawb/zero/internal/zeroruntime"
+)
+
+func TestClipBytesHandlesTinyLimitsOnRuneBoundaries(t *testing.T) {
+	for _, limit := range []int{0, 1, 2, 3} {
+		if clipped := clipBytes("世界", limit); len(clipped) > limit || !utf8.ValidString(clipped) {
+			t.Fatalf("clipBytes limit %d returned invalid result %q", limit, clipped)
+		}
+	}
+}
+
+func TestBoundaryClippersHandleNonPositiveLimits(t *testing.T) {
+	for _, clip := range []func(string, int) string{clipPrefixAtBoundary, clipSuffixAtBoundary} {
+		for _, limit := range []int{-1, 0} {
+			if got := clip("世界", limit); got != "" {
+				t.Fatalf("clipper limit %d = %q, want empty", limit, got)
+			}
+		}
+	}
+}
+
+func TestProjectCompactionInputDropsRecoverableToolBodies(t *testing.T) {
+	largeBody := strings.Repeat("recoverable source line\n", 1000)
+	messages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleUser, Content: "Inspect the parser and preserve its current behavior."},
+		{Role: zeroruntime.MessageRoleAssistant, Content: "I will inspect before editing.", ToolCalls: []zeroruntime.ToolCall{{ID: "read", Name: "read_file", Arguments: `{"path":"internal/parser.go"}`}}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "read", Content: largeBody},
+		{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{{ID: "test", Name: "exec_command", Arguments: `{"cmd":"go test ./internal/parser"}`}}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "test", Content: "Error: parser regression\nlong diagnostic details"},
+	}
+
+	projection := projectCompactionInput(messages)
+	projected := projection.messages
+	if len(projected) != 1 {
+		t.Fatalf("projection = %#v, want one compact message", projected)
+	}
+	content := projected[0].Content
+	for _, want := range []string{"Inspect the parser", `read_file "internal/parser.go"`, `exec_command "go test ./internal/parser"`, "Error: parser regression"} {
+		if !strings.Contains(content, want) {
+			t.Fatalf("projection missing %q: %q", want, content)
+		}
+	}
+	if strings.Contains(content, "recoverable source line") || strings.Contains(content, "long diagnostic details") {
+		t.Fatalf("projection retained reconstructible or overlong tool output: %q", content)
+	}
+	if estimateTokens(projected)*20 >= estimateTokens(messages) {
+		t.Fatalf("projection did not materially reduce tokens: before=%d after=%d", estimateTokens(messages), estimateTokens(projected))
+	}
+}
+
+func TestProjectCompactionInputRetainsStructurallyMarkedToolErrors(t *testing.T) {
+	messages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{{ID: "git", Name: "exec_command", Arguments: `{"cmd":"git status"}`}}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "git", Content: "fatal: not a git repository", IsError: true},
+	}
+
+	projected := projectCompactionInput(messages).messages
+	if len(projected) != 1 || !strings.Contains(projected[0].Content, "fatal: not a git repository") {
+		t.Fatalf("structured tool error was dropped from projection: %#v", projected)
+	}
+}
+
+func TestProjectCompactionInputRetainsAskUserExchangeAndSemanticArguments(t *testing.T) {
+	messages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{{ID: "ask", Name: "ask_user", Arguments: `{"questions":[{"question":"Which database should remain?"}]}`}}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "ask", Content: "Which database should remain?: Postgres only; do not touch MySQL."},
+		{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{
+			{ID: "patch", Name: "apply_patch", Arguments: `{"patch":"*** Begin Patch\n*** Update File: internal/db.go\n*** End Patch"}`},
+			{ID: "fetch", Name: "web_fetch", Arguments: `{"url":"https://example.com/spec"}`},
+			{ID: "task", Name: "task", Arguments: `{"prompt":"Inspect the Windows implementation"}`},
+		}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "patch", Content: "Done!", ChangedFiles: []string{"internal/db.go"}},
+	}
+
+	content := projectCompactionInput(messages).messages[0].Content
+	for _, want := range []string{"Which database should remain?", "Postgres only; do not touch MySQL", "internal/db.go", "https://example.com/spec", "Inspect the Windows implementation"} {
+		if !strings.Contains(content, want) {
+			t.Fatalf("projection missing %q: %q", want, content)
+		}
+	}
+}
+
+func TestProjectCompactionInputCapsToolCallsPerTurn(t *testing.T) {
+	calls := make([]zeroruntime.ToolCall, 12)
+	for index := range calls {
+		calls[index] = zeroruntime.ToolCall{Name: "read_file", Arguments: `{"path":"file.go"}`}
+	}
+	projected := projectCompactionInput([]zeroruntime.Message{{Role: zeroruntime.MessageRoleAssistant, ToolCalls: calls}}).messages
+	content := projected[0].Content
+	if strings.Count(content, "* read_file") != compactionToolCallsPerTurn || !strings.Contains(content, "4 earlier tool calls omitted") {
+		t.Fatalf("tool-call tail was not bounded: %q", content)
+	}
+}
+
+func TestProjectCompactionInputCarriesPreviousSummaryOutsideBriefCap(t *testing.T) {
+	previous := "keep the earlier architecture decision\n" + strings.Repeat("prior detail ", 2000) + "\nkeep the newest prior decision"
+	messages := []zeroruntime.Message{{Role: zeroruntime.MessageRoleUser, Content: summaryLabel + "\n" + previous + "\n\n" + preservedStateLabel + "\n{}"}}
+	for index := range 500 {
+		messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, Content: strings.Repeat("later transcript detail ", 20)})
+		messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "later request " + strings.Repeat("context ", 20) + string(rune('a'+index%26))})
+	}
+
+	projection := projectCompactionInput(messages)
+	content := projection.messages[0].Content
+	if !strings.Contains(content, "[previous summary]\nkeep the earlier architecture decision") || !strings.Contains(content, "keep the newest prior decision") {
+		t.Fatalf("previous summary was lost when the brief tail was capped: %q", content)
+	}
+	if !strings.Contains(content, "middle transcript omitted to fit compaction budget") {
+		t.Fatalf("oversized brief was not head/tail capped: %q", content)
+	}
+	if !projection.truncated {
+		t.Fatal("projection did not structurally report truncation")
+	}
+}
+
+func TestProjectCompactionInputDoesNotInferTruncationFromUserText(t *testing.T) {
+	projection := projectCompactionInput([]zeroruntime.Message{{
+		Role: zeroruntime.MessageRoleUser, Content: "Keep this literal marker: [middle omitted]",
+	}})
+	if projection.truncated {
+		t.Fatal("literal user text produced a false truncation signal")
+	}
+}

internal/agent/compaction_recent_edits_test.go

@@ -20,11 +20,15 @@ func TestRecentEditsExtractsPathsAndNotes(t *testing.T) {
 			{ID: "e2", Name: "edit_file", Arguments: `{"path":"internal/bar.go","old_string":"a","new_string":"b"}`},
 		}},
 		{Role: zeroruntime.MessageRoleTool, ToolCallID: "e2", Content: "Applied edit to internal/bar.go"},
+		{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{
+			{ID: "e3", Name: "apply_patch", Arguments: `{"patch":"*** Update File: internal/baz.go"}`},
+		}},
+		{Role: zeroruntime.MessageRoleTool, ToolCallID: "e3", Content: "Done!", ChangedFiles: []string{"internal/baz.go"}},
 	}
 
 	edits := recentEdits(messages)
-	if len(edits) != 2 {
-		t.Fatalf("expected 2 edited files, got %d: %#v", len(edits), edits)
+	if len(edits) != 3 {
+		t.Fatalf("expected 3 edited files, got %d: %#v", len(edits), edits)
 	}
 	if edits[0].name != "internal/foo.go" || !strings.Contains(edits[0].body, "12 lines") {
 		t.Fatalf("first edit = %#v, want foo.go with its note", edits[0])
@@ -32,6 +36,9 @@ func TestRecentEditsExtractsPathsAndNotes(t *testing.T) {
 	if edits[1].name != "internal/bar.go" || !strings.Contains(edits[1].body, "Applied edit") {
 		t.Fatalf("second edit = %#v, want bar.go with its note", edits[1])
 	}
+	if edits[2].name != "internal/baz.go" || edits[2].body != "Done!" {
+		t.Fatalf("third edit = %#v, want apply_patch changed file with its note", edits[2])
+	}
 }
 
 // After compaction elides the editing turns, the preserved-state block still

internal/agent/compaction_test.go

@@ -7,6 +7,7 @@ import (
 	"testing"
 
 	"github.com/Gitlawb/zero/internal/tools"
+	"github.com/Gitlawb/zero/internal/trace"
 	"github.com/Gitlawb/zero/internal/zeroruntime"
 )
 
@@ -58,12 +59,15 @@ func TestCompactKeepsSystemAndPreservedSuffix(t *testing.T) {
 	if last.Content != "most recent question" {
 		t.Fatalf("expected most recent message preserved, got %q", last.Content)
 	}
-	// The summarized middle excludes system and preserved suffix.
-	if len(captured) != 3 {
-		t.Fatalf("expected 3 summarized messages, got %d: %#v", len(captured), captured)
+	// The summarizer receives a compact semantic projection of the middle rather
+	// than reconstructible raw tool output.
+	if len(captured) != 1 || captured[0].Role != zeroruntime.MessageRoleUser {
+		t.Fatalf("expected one projected summary input, got %#v", captured)
 	}
-	if captured[0].Content != "first question" {
-		t.Fatalf("expected oldest non-system message first, got %#v", captured[0])
+	for _, want := range []string{"[user #0]", "first question", "[assistant #1]", "first answer", "second question"} {
+		if !strings.Contains(captured[0].Content, want) {
+			t.Fatalf("projected summary input missing %q: %q", want, captured[0].Content)
+		}
 	}
 	// Compaction must shrink the conversation.
 	if estimateTokens(result) >= estimateTokens(messages) {
@@ -425,6 +429,7 @@ type reactiveProvider struct {
 	summarizeCalls int
 	turnRequests   int
 	failedOnce     bool
+	connectError   bool
 	bigText        string
 	finalText      string
 }
@@ -446,6 +451,9 @@ func (provider *reactiveProvider) StreamCompletion(ctx context.Context, request
 		return streamEvents(toolTurnWithText(provider.bigText, "1", "read_file", `{"path":"x"}`)), nil
 	case provider.turnRequests == 2 && !provider.failedOnce:
 		provider.failedOnce = true
+		if provider.connectError {
+			return nil, errors.New("context_length_exceeded")
+		}
 		return streamEvents([]zeroruntime.StreamEvent{
 			{Type: zeroruntime.StreamEventError, Error: "This model's maximum context length is 1000 tokens. Please reduce the length of the messages."},
 		}), nil
@@ -454,6 +462,39 @@ func (provider *reactiveProvider) StreamCompletion(ctx context.Context, request
 	}
 }
 
+func TestRunConnectErrorCompactionRecordsReplacementPlan(t *testing.T) {
+	provider := &reactiveProvider{
+		connectError: true,
+		bigText:      strings.Repeat("b", 6000),
+		finalText:    "recovered",
+	}
+	registry := tools.NewRegistry()
+	registry.Register(tools.NewScopedReadFileTool(t.TempDir(), nil))
+	recorder := trace.NewRecorder("connect-compaction", "run-1", "test")
+	var contextPlans []ContextBreakdown
+
+	result, err := Run(context.Background(), strings.Repeat("z", 6000), provider, Options{
+		Registry:               registry,
+		PermissionMode:         PermissionModeUnsafe,
+		ContextWindow:          10_000_000,
+		CompactionPreserveLast: 2,
+		Trace:                  recorder,
+		OnContext: func(breakdown ContextBreakdown) {
+			contextPlans = append(contextPlans, breakdown)
+		},
+	})
+	if err != nil || result.FinalAnswer != "recovered" {
+		t.Fatalf("connect-error compaction failed: result=%#v err=%v", result, err)
+	}
+	if len(contextPlans) != 3 || contextPlans[2].MessageTokens >= contextPlans[1].MessageTokens {
+		t.Fatalf("replacement request context not reported: %#v", contextPlans)
+	}
+	gotTrace := recorder.Finish()
+	if len(gotTrace.PrefixHashes) != 4 || gotTrace.PrefixHashes[3].InvalidationReason != "unchanged" {
+		t.Fatalf("replacement request trace not recorded: %#v", gotTrace.PrefixHashes)
+	}
+}
+
 func TestRunReactiveCompactionRecovers(t *testing.T) {
 	provider := &reactiveProvider{
 		bigText:   strings.Repeat("b", 6000),
@@ -465,6 +506,8 @@ func TestRunReactiveCompactionRecovers(t *testing.T) {
 	// bloats the history.
 	registry := tools.NewRegistry()
 	registry.Register(tools.NewScopedReadFileTool(t.TempDir(), nil))
+	recorder := trace.NewRecorder("reactive-compaction", "run-1", "test")
+	var contextPlans []ContextBreakdown
 
 	// ContextWindow large enough that proactive compaction never triggers, so
 	// only the reactive path can save the run.
@@ -473,6 +516,10 @@ func TestRunReactiveCompactionRecovers(t *testing.T) {
 		PermissionMode:         PermissionModeUnsafe,
 		ContextWindow:          10_000_000,
 		CompactionPreserveLast: 2,
+		Trace:                  recorder,
+		OnContext: func(breakdown ContextBreakdown) {
+			contextPlans = append(contextPlans, breakdown)
+		},
 	})
 	if err != nil {
 		t.Fatalf("expected reactive compaction to recover the run, got error: %v", err)
@@ -483,6 +530,25 @@ func TestRunReactiveCompactionRecovers(t *testing.T) {
 	if provider.summarizeCalls == 0 {
 		t.Fatal("expected reactive compaction to invoke the summarizer")
 	}
+	if len(contextPlans) != 3 {
+		t.Fatalf("main request context callbacks = %d, want initial turns plus compacted retry", len(contextPlans))
+	}
+	if contextPlans[2].MessageTokens >= contextPlans[1].MessageTokens {
+		t.Fatalf("retry context was not updated after compaction: before=%d after=%d", contextPlans[1].MessageTokens, contextPlans[2].MessageTokens)
+	}
+	gotTrace := recorder.Finish()
+	if len(gotTrace.PrefixHashes) != 4 {
+		t.Fatalf("prefix evidence count = %d, want two turns, compaction, and retry: %#v", len(gotTrace.PrefixHashes), gotTrace.PrefixHashes)
+	}
+	if gotTrace.PrefixHashes[0].InvalidationReason != "initial" ||
+		gotTrace.PrefixHashes[1].InvalidationReason != "unchanged" ||
+		gotTrace.PrefixHashes[2].InvalidationReason != "initial" ||
+		gotTrace.PrefixHashes[3].InvalidationReason != "unchanged" {
+		t.Fatalf("unexpected request-specific invalidation evidence: %#v", gotTrace.PrefixHashes)
+	}
+	if gotTrace.PrefixHashes[2].CompletePrefixHash == gotTrace.PrefixHashes[1].CompletePrefixHash {
+		t.Fatalf("compaction fingerprint reused the main request prefix: %#v", gotTrace.PrefixHashes)
+	}
 }
 
 // midStreamReactiveProvider forwards some text BEFORE surfacing a context-limit

internal/agent/context_measurement.go

@@ -23,6 +23,24 @@ type ContextBreakdown struct {
 	TotalTokens   int     // SystemTokens + ToolTokens + MessageTokens
 	ContextWindow int     // model context window; 0 when unknown
 	UsedFraction  float64 // TotalTokens / ContextWindow; 0 when window unknown
+	// Blocks explain why each model-visible category is present without exposing
+	// its content. The planner currently preserves all three categories.
+	Blocks []ContextBlock
+	// CompletePrefixHash identifies the provider-visible system+tool prefix.
+	CompletePrefixHash string
+	// PrefixInvalidationReason is "initial", "unchanged", or a stable comma-
+	// separated list of changed prefix categories.
+	PrefixInvalidationReason string
+}
+
+// ContextBlock is content-free evidence for one model-visible context category.
+type ContextBlock struct {
+	Kind        string
+	Tokens      int
+	CacheClass  string
+	Authority   string
+	Recoverable bool
+	Reason      string
 }
 
 // MeasureContext estimates the per-category token footprint of a request: the
@@ -41,6 +59,24 @@ func MeasureContext(messages []zeroruntime.Message, tools []zeroruntime.ToolDefi
 		ContextWindow: contextWindow,
 	}
 	breakdown.TotalTokens = breakdown.SystemTokens + breakdown.ToolTokens + breakdown.MessageTokens
+	if breakdown.SystemTokens > 0 {
+		breakdown.Blocks = append(breakdown.Blocks, ContextBlock{
+			Kind: "system", Tokens: breakdown.SystemTokens, CacheClass: "stable_prefix",
+			Authority: "required", Reason: "instructions, workspace policy, and safety policy",
+		})
+	}
+	if breakdown.ToolTokens > 0 {
+		breakdown.Blocks = append(breakdown.Blocks, ContextBlock{
+			Kind: "tools", Tokens: breakdown.ToolTokens, CacheClass: "stable_prefix",
+			Authority: "capability", Reason: "currently permitted and selected tool definitions",
+		})
+	}
+	if breakdown.MessageTokens > 0 {
+		breakdown.Blocks = append(breakdown.Blocks, ContextBlock{
+			Kind: "conversation", Tokens: breakdown.MessageTokens, CacheClass: "dynamic_tail",
+			Authority: "transcript", Reason: "valid provider replay history and current task context",
+		})
+	}
 	if contextWindow > 0 {
 		breakdown.UsedFraction = float64(breakdown.TotalTokens) / float64(contextWindow)
 	}

internal/agent/context_measurement_test.go

@@ -32,6 +32,9 @@ func TestMeasureContextSplitsByCategory(t *testing.T) {
 	if breakdown.UsedFraction != wantFraction {
 		t.Fatalf("UsedFraction = %v, want %v", breakdown.UsedFraction, wantFraction)
 	}
+	if len(breakdown.Blocks) != 3 {
+		t.Fatalf("Blocks = %#v, want system/tools/conversation", breakdown.Blocks)
+	}
 }
 
 func TestMeasureContextUnknownWindowHasZeroFraction(t *testing.T) {

internal/agent/context_planner.go

@@ -0,0 +1,183 @@
+package agent
+
+import (
+	"strings"
+
+	"github.com/Gitlawb/zero/internal/zeroruntime"
+)
+
+type contextPlannerConfig struct {
+	contextWindow  int
+	promptCacheKey string
+	promptParts    systemPromptParts
+}
+
+// contextPlanner is the single seam for constructing model-visible requests.
+// Planning is deterministic and does not retrieve content, execute tools, or
+// change permissions. The initial implementation deliberately preserves every
+// message and tool definition while making composition and cache drift
+// inspectable; later selection policies must continue to cross this seam.
+type contextPlanner struct {
+	config          contextPlannerConfig
+	previousPrefix  prefixFingerprint
+	hasPrevious     bool
+	toolSnapshotKey string
+	toolSnapshot    []zeroruntime.ToolDefinition
+}
+
+type contextPlan struct {
+	Request           zeroruntime.CompletionRequest
+	Breakdown         ContextBreakdown
+	PrefixFingerprint prefixFingerprint
+}
+
+func newContextPlanner(config contextPlannerConfig) *contextPlanner {
+	return &contextPlanner{config: config}
+}
+
+// Plan returns a provider request snapshot plus content-free accounting.
+// It intentionally performs no relevance filtering: preserving current model
+// capability is the baseline contract for future planner policies.
+func (planner *contextPlanner) Plan(messages []zeroruntime.Message, toolDefs []zeroruntime.ToolDefinition, reasoningEffort string) contextPlan {
+	return planner.plan(messages, toolDefs, reasoningEffort, planner.config.promptParts)
+}
+
+// planWithPromptParts plans a request whose stable system sections differ from
+// the planner's configured main-run prompt, such as a compaction summary call.
+func (planner *contextPlanner) planWithPromptParts(messages []zeroruntime.Message, toolDefs []zeroruntime.ToolDefinition, reasoningEffort string, parts systemPromptParts) contextPlan {
+	return planner.plan(messages, toolDefs, reasoningEffort, parts)
+}
+
+func (planner *contextPlanner) plan(messages []zeroruntime.Message, toolDefs []zeroruntime.ToolDefinition, reasoningEffort string, parts systemPromptParts) contextPlan {
+	requestMessages := copyMessages(messages)
+	requestSystemPrompt := leadingSystemContent(requestMessages)
+	if parts.prompt != requestSystemPrompt {
+		// Component boundaries from a different request would make the detailed
+		// invalidation reason misleading. Retain the exact request prefix and
+		// classify it conservatively as an unstructured system prompt instead.
+		parts = systemPromptParts{prompt: requestSystemPrompt}
+	}
+	fingerprint := computePrefixFingerprint(buildPromptSubstringsFromParts(parts, toolDefs))
+	request := zeroruntime.CompletionRequest{
+		Messages:        requestMessages,
+		Tools:           planner.snapshotTools(toolDefs, fingerprint),
+		ReasoningEffort: reasoningEffort,
+		PromptCacheKey:  planner.config.promptCacheKey,
+	}
+	breakdown := MeasureContext(request.Messages, request.Tools, planner.config.contextWindow)
+	breakdown.CompletePrefixHash = fingerprint.CompletePrefixHash
+	var previous *prefixFingerprint
+	if planner.hasPrevious {
+		previous = &planner.previousPrefix
+	}
+	breakdown.PrefixInvalidationReason = explainPrefixChange(previous, fingerprint)
+	planner.previousPrefix = fingerprint
+	planner.hasPrevious = true
+	return contextPlan{
+		Request:           request,
+		Breakdown:         breakdown,
+		PrefixFingerprint: fingerprint,
+	}
+}
+
+// snapshotTools freezes provider-visible tool definitions when their semantic
+// fingerprint changes. Stable turns reuse the frozen schemas instead of
+// recursively cloning every map and slice for every request.
+func (planner *contextPlanner) snapshotTools(toolDefs []zeroruntime.ToolDefinition, fingerprint prefixFingerprint) []zeroruntime.ToolDefinition {
+	key := fingerprint.ToolsHash + "\x00" + fingerprint.SchemaHash
+	if planner.toolSnapshotKey != key {
+		planner.toolSnapshot = copyToolDefinitions(toolDefs)
+		planner.toolSnapshotKey = key
+	}
+	return planner.toolSnapshot
+}
+
+func copyToolDefinitions(toolDefs []zeroruntime.ToolDefinition) []zeroruntime.ToolDefinition {
+	if toolDefs == nil {
+		return nil
+	}
+	copied := make([]zeroruntime.ToolDefinition, len(toolDefs))
+	for index, definition := range toolDefs {
+		copied[index] = definition
+		copied[index].Parameters = copySchemaMap(definition.Parameters)
+	}
+	return copied
+}
+
+func copySchemaMap(schema map[string]any) map[string]any {
+	if schema == nil {
+		return nil
+	}
+	copied := make(map[string]any, len(schema))
+	for key, value := range schema {
+		copied[key] = copySchemaValue(value)
+	}
+	return copied
+}
+
+func copySchemaValue(value any) any {
+	switch typed := value.(type) {
+	case map[string]any:
+		return copySchemaMap(typed)
+	case []any:
+		copied := make([]any, len(typed))
+		for index, item := range typed {
+			copied[index] = copySchemaValue(item)
+		}
+		return copied
+	case []string:
+		return append([]string(nil), typed...)
+	default:
+		return value
+	}
+}
+
+func leadingSystemContent(messages []zeroruntime.Message) string {
+	contents := make([]string, 0, 1)
+	for _, message := range messages {
+		if message.Role != zeroruntime.MessageRoleSystem {
+			break
+		}
+		contents = append(contents, message.Content)
+	}
+	return strings.Join(contents, "\n\n")
+}
+
+func explainPrefixChange(previous *prefixFingerprint, current prefixFingerprint) string {
+	if previous == nil {
+		return "initial"
+	}
+	if previous.CompletePrefixHash == current.CompletePrefixHash {
+		return "unchanged"
+	}
+	reasons := make([]string, 0, 3)
+	if previous.SystemPromptHash != current.SystemPromptHash {
+		parts := make([]string, 0, 4)
+		if previous.BaseInstructionsHash != current.BaseInstructionsHash {
+			parts = append(parts, "base_instructions")
+		}
+		if previous.ConfirmationPolicyHash != current.ConfirmationPolicyHash {
+			parts = append(parts, "confirmation_policy")
+		}
+		if previous.ProjectContextHash != current.ProjectContextHash {
+			parts = append(parts, "project_context")
+		}
+		if previous.SkillsHash != current.SkillsHash {
+			parts = append(parts, "skills")
+		}
+		if len(parts) == 0 {
+			parts = append(parts, "system_prompt")
+		}
+		reasons = append(reasons, parts...)
+	}
+	if previous.ToolsHash != current.ToolsHash {
+		reasons = append(reasons, "tools")
+	}
+	if previous.SchemaHash != current.SchemaHash {
+		reasons = append(reasons, "schema")
+	}
+	if len(reasons) == 0 {
+		return "prefix_changed"
+	}
+	return strings.Join(reasons, ",")
+}

internal/agent/context_planner_test.go

@@ -0,0 +1,185 @@
+package agent
+
+import (
+	"reflect"
+	"testing"
+
+	"github.com/Gitlawb/zero/internal/zeroruntime"
+)
+
+func TestContextPlannerPreservesProviderRequest(t *testing.T) {
+	messages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleSystem, Content: "system"},
+		{Role: zeroruntime.MessageRoleUser, Content: "inspect this", Images: []zeroruntime.ImageBlock{{MediaType: "image/png", Data: []byte{1, 2, 3}}}},
+		{Role: zeroruntime.MessageRoleAssistant, Content: "working", ToolCalls: []zeroruntime.ToolCall{{ID: "call-1", Name: "read_file", Arguments: `{"path":"main.go"}`}}, Reasoning: []zeroruntime.ReasoningBlock{{Provider: "test", Type: "thinking", Signature: "sig"}}},
+	}
+	toolDefs := []zeroruntime.ToolDefinition{{
+		Name: "read_file", Description: "Read a file",
+		Parameters: map[string]any{
+			"type":       "object",
+			"required":   []string{"path"},
+			"properties": map[string]any{"path": map[string]any{"type": "string"}},
+			"anyOf":      []any{map[string]any{"type": "object"}},
+		},
+	}}
+	planner := newContextPlanner(contextPlannerConfig{
+		contextWindow:  128_000,
+		promptCacheKey: "session-1",
+		promptParts:    systemPromptParts{prompt: "system", baseInstructions: "system"},
+	})
+
+	plan := planner.Plan(messages, toolDefs, "medium")
+	want := zeroruntime.CompletionRequest{
+		Messages:        copyMessages(messages),
+		Tools:           toolDefs,
+		ReasoningEffort: "medium",
+		PromptCacheKey:  "session-1",
+	}
+	if !reflect.DeepEqual(plan.Request, want) {
+		t.Fatalf("planned request changed provider input:\n got: %#v\nwant: %#v", plan.Request, want)
+	}
+	stable := planner.Plan(messages, toolDefs, "medium")
+	if &stable.Request.Tools[0] != &plan.Request.Tools[0] {
+		t.Fatal("stable tool fingerprint rebuilt the immutable schema snapshot")
+	}
+
+	// A plan owns its request snapshot; later caller mutation cannot change its
+	// messages or its recursively nested tool schema.
+	messages[1].Content = "changed"
+	messages[1].Images[0].Data[0] = 9
+	toolDefs[0].Name = "changed_tool"
+	toolDefs[0].Parameters["required"].([]string)[0] = "other"
+	toolDefs[0].Parameters["properties"].(map[string]any)["path"].(map[string]any)["type"] = "integer"
+	toolDefs[0].Parameters["anyOf"].([]any)[0].(map[string]any)["type"] = "array"
+	if plan.Request.Messages[1].Content != "inspect this" || plan.Request.Messages[1].Images[0].Data[0] != 1 {
+		t.Fatalf("planned messages alias caller state: %#v", plan.Request.Messages[1])
+	}
+	if plan.Request.Tools[0].Name != "read_file" ||
+		plan.Request.Tools[0].Parameters["required"].([]string)[0] != "path" ||
+		plan.Request.Tools[0].Parameters["properties"].(map[string]any)["path"].(map[string]any)["type"] != "string" ||
+		plan.Request.Tools[0].Parameters["anyOf"].([]any)[0].(map[string]any)["type"] != "object" {
+		t.Fatalf("planned tools alias caller state: %#v", plan.Request.Tools[0])
+	}
+
+	next := planner.Plan(messages, toolDefs, "medium")
+	if next.PrefixFingerprint == plan.PrefixFingerprint || next.Request.Tools[0].Name != "changed_tool" {
+		t.Fatalf("changed tool schema did not refresh snapshot: %#v", next)
+	}
+	if plan.Request.Tools[0].Name != "read_file" {
+		t.Fatalf("refresh mutated earlier request: %#v", plan.Request.Tools[0])
+	}
+}
+
+func TestContextPlannerReportsInspectableBlocks(t *testing.T) {
+	planner := newContextPlanner(contextPlannerConfig{contextWindow: 100_000})
+	plan := planner.Plan([]zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleSystem, Content: filler(400)},
+		{Role: zeroruntime.MessageRoleUser, Content: filler(200)},
+	}, []zeroruntime.ToolDefinition{{Name: "read_file", Description: "Read a file"}}, "")
+
+	if plan.Breakdown.PrefixInvalidationReason != "initial" || plan.Breakdown.CompletePrefixHash == "" {
+		t.Fatalf("prefix evidence = %#v", plan.Breakdown)
+	}
+	if len(plan.Breakdown.Blocks) != 3 {
+		t.Fatalf("blocks = %#v, want system/tools/conversation", plan.Breakdown.Blocks)
+	}
+	wantKinds := []string{"system", "tools", "conversation"}
+	total := 0
+	for index, block := range plan.Breakdown.Blocks {
+		if block.Kind != wantKinds[index] || block.Tokens <= 0 || block.Reason == "" || block.Authority == "" || block.CacheClass == "" {
+			t.Fatalf("block %d = %#v", index, block)
+		}
+		total += block.Tokens
+	}
+	if total != plan.Breakdown.TotalTokens {
+		t.Fatalf("block tokens = %d, want total %d", total, plan.Breakdown.TotalTokens)
+	}
+}
+
+func TestContextPlannerFingerprintsActualRequestSystemPrompt(t *testing.T) {
+	planner := newContextPlanner(contextPlannerConfig{promptParts: systemPromptParts{
+		prompt: "configured system", baseInstructions: "configured system",
+	}})
+	messages := []zeroruntime.Message{
+		{Role: zeroruntime.MessageRoleSystem, Content: "request-specific system"},
+		{Role: zeroruntime.MessageRoleUser, Content: "task"},
+	}
+
+	plan := planner.Plan(messages, nil, "")
+	want := computePrefixFingerprint(buildPromptSubstringsFromParts(
+		systemPromptParts{prompt: "request-specific system"}, nil,
+	))
+	if plan.PrefixFingerprint != want {
+		t.Fatalf("fingerprint describes configured prompt instead of request:\n got: %#v\nwant: %#v", plan.PrefixFingerprint, want)
+	}
+}
+
+func TestContextPlannerExplainsPrefixInvalidation(t *testing.T) {
+	planner := newContextPlanner(contextPlannerConfig{promptParts: systemPromptParts{
+		prompt: "system", baseInstructions: "base", projectContext: "project",
+	}})
+	messages := []zeroruntime.Message{{Role: zeroruntime.MessageRoleSystem, Content: "system"}, {Role: zeroruntime.MessageRoleUser, Content: "task"}}
+	tools := []zeroruntime.ToolDefinition{{Name: "read_file", Description: "Read", Parameters: map[string]any{"type": "object"}}}
+
+	if got := planner.Plan(messages, tools, "").Breakdown.PrefixInvalidationReason; got != "initial" {
+		t.Fatalf("first reason = %q, want initial", got)
+	}
+	if got := planner.Plan(messages, tools, "").Breakdown.PrefixInvalidationReason; got != "unchanged" {
+		t.Fatalf("stable reason = %q, want unchanged", got)
+	}
+	tools[0].Description = "Read an exact file"
+	if got := planner.Plan(messages, tools, "").Breakdown.PrefixInvalidationReason; got != "tools" {
+		t.Fatalf("tool reason = %q, want tools", got)
+	}
+	tools[0].Parameters["required"] = []any{"path"}
+	if got := planner.Plan(messages, tools, "").Breakdown.PrefixInvalidationReason; got != "schema" {
+		t.Fatalf("schema reason = %q, want schema", got)
+	}
+	planner.config.promptParts.prompt = "system with changed project"
+	planner.config.promptParts.projectContext = "changed project"
+	messages[0].Content = "system with changed project"
+	if got := planner.Plan(messages, tools, "").Breakdown.PrefixInvalidationReason; got != "project_context" {
+		t.Fatalf("project reason = %q, want project_context", got)
+	}
+}
+
+func TestExplainPrefixChangeNamesEveryChangedComponent(t *testing.T) {
+	baseline := prefixFingerprint{
+		SystemPromptHash:       "system",
+		BaseInstructionsHash:   "base",
+		ConfirmationPolicyHash: "policy",
+		ProjectContextHash:     "project",
+		SkillsHash:             "skills",
+		ToolsHash:              "tools",
+		SchemaHash:             "schema",
+		CompletePrefixHash:     "complete",
+	}
+	tests := []struct {
+		name   string
+		mutate func(*prefixFingerprint)
+		want   string
+	}{
+		{name: "base instructions", mutate: func(value *prefixFingerprint) {
+			value.SystemPromptHash, value.BaseInstructionsHash = "changed", "changed"
+		}, want: "base_instructions"},
+		{name: "confirmation policy", mutate: func(value *prefixFingerprint) {
+			value.SystemPromptHash, value.ConfirmationPolicyHash = "changed", "changed"
+		}, want: "confirmation_policy"},
+		{name: "project context", mutate: func(value *prefixFingerprint) {
+			value.SystemPromptHash, value.ProjectContextHash = "changed", "changed"
+		}, want: "project_context"},
+		{name: "skills", mutate: func(value *prefixFingerprint) { value.SystemPromptHash, value.SkillsHash = "changed", "changed" }, want: "skills"},
+		{name: "unclassified system prompt", mutate: func(value *prefixFingerprint) { value.SystemPromptHash = "changed" }, want: "system_prompt"},
+		{name: "tools and schema", mutate: func(value *prefixFingerprint) { value.ToolsHash, value.SchemaHash = "changed", "changed" }, want: "tools,schema"},
+	}
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			current := baseline
+			test.mutate(&current)
+			current.CompletePrefixHash = "changed"
+			if got := explainPrefixChange(&baseline, current); got != test.want {
+				t.Fatalf("reason = %q, want %q", got, test.want)
+			}
+		})
+	}
+}

internal/agent/loop.go

@@ -183,10 +183,22 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 	defer runPermissions.cleanup()
 
 	promptParts := buildSystemPromptParts(options)
+	planner := newContextPlanner(contextPlannerConfig{
+		contextWindow:  options.ContextWindow,
+		promptCacheKey: options.SessionID,
+		promptParts:    promptParts,
+	})
 	messages := zeroruntime.SeedMessagesWithImages(promptParts.prompt, prompt, options.Images)
 
 	guards := newGuardState()
 	task := newTaskState(prompt, options.Trace)
+	onPermission := options.OnPermission
+	options.OnPermission = func(event PermissionEvent) {
+		task.observe(taskStateEvent{kind: taskStateEventPermission, permission: event})
+		if onPermission != nil {
+			onPermission(event)
+		}
+	}
 	compactor := newCompactionState(options, task)
 	defer func() {
 		// A final transcript comparison is observational. It records drift but
@@ -275,42 +287,15 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 		exposed, _ := partitionToolsCached(registry, permissionMode, options, loaded, toolDefCache)
 		toolPartitionSpan.End()
 
-		// Fingerprint the exact system prompt built at run start plus this turn's
-		// provider-visible tool definitions in their emitted order. Reusing the
-		// retained prompt parts avoids rebuilding workspace context while ensuring
-		// the trace describes the same bytes carried by the request.
-		if options.Trace != nil {
-			fp := computePrefixFingerprint(buildPromptSubstringsFromParts(promptParts, exposed))
-			options.Trace.EmitPrefixHash(trace.PrefixHash{
-				SystemPromptHash:       fp.SystemPromptHash,
-				BaseInstructionsHash:   fp.BaseInstructionsHash,
-				ConfirmationPolicyHash: fp.ConfirmationPolicyHash,
-				ProjectContextHash:     fp.ProjectContextHash,
-				SkillsHash:             fp.SkillsHash,
-				ToolsHash:              fp.ToolsHash,
-				SchemaHash:             fp.SchemaHash,
-				CompletePrefixHash:     fp.CompletePrefixHash,
-			})
-		}
-
 		// PROACTIVE compaction: if the history is approaching the model's
 		// context window, summarize the oldest middle before building the
 		// request. A no-op when ContextWindow == 0 (compaction disabled).
 		compactionSpan := options.Trace.Span(trace.SpanCompaction)
 		messages = compactor.maybeCompact(ctx, provider, messages, exposed)
 		compactionSpan.End()
-		request := zeroruntime.CompletionRequest{
-			Messages:        copyMessages(messages),
-			Tools:           exposed,
-			ReasoningEffort: options.ReasoningEffort,
-			PromptCacheKey:  options.SessionID,
-		}
-
-		// Report the per-category context budget for this turn so a surface can
-		// show utilization. Opt-in: a no-op when OnContext is unset.
-		if options.OnContext != nil {
-			options.OnContext(MeasureContext(messages, request.Tools, options.ContextWindow))
-		}
+		plan := planner.Plan(messages, exposed, options.ReasoningEffort)
+		request := plan.Request
+		recordContextPlan(options, plan)
 
 		// A transient upstream disconnect on the initial connect is retried with
 		// backoff (before any content is forwarded, so no OnText is duplicated);
@@ -335,12 +320,9 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 				// on registry+loaded, not on the messages, so they stay valid after
 				// compaction. Using the bare toolDefinitions here would route through an
 				// empty-loaded partition, re-hiding every already-loaded deferred tool.
-				request = zeroruntime.CompletionRequest{
-					Messages:        copyMessages(messages),
-					Tools:           exposed,
-					ReasoningEffort: options.ReasoningEffort,
-					PromptCacheKey:  options.SessionID,
-				}
+				retryPlan := planner.Plan(messages, exposed, options.ReasoningEffort)
+				request = retryPlan.Request
+				recordContextPlan(options, retryPlan)
 				// Pre-content connect after a context-limit compaction: route through the
 				// reconnect helper so a transient upstream hiccup here doesn't fail the
 				// whole run and re-burn every token (AUDIT-L1).
@@ -424,12 +406,9 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 				// Reuse the SAME active-mode partition (exposed) from this turn rather
 				// than the bare toolDefinitions: exposed depends on registry+loaded (not
 				// the messages), so it stays valid after compaction.
-				retryRequest := zeroruntime.CompletionRequest{
-					Messages:        copyMessages(messages),
-					Tools:           exposed,
-					ReasoningEffort: options.ReasoningEffort,
-					PromptCacheKey:  options.SessionID,
-				}
+				retryPlan := planner.Plan(messages, exposed, options.ReasoningEffort)
+				retryRequest := retryPlan.Request
+				recordContextPlan(options, retryPlan)
 				retryStream, retryStreamErr := streamWithReconnect(ctx, provider, retryRequest, reconnectNoticeFor(options))
 				if retryStreamErr != nil {
 					return collected, retryStreamErr
@@ -487,12 +466,9 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 				result.Messages = copyMessages(messages)
 				return result, err
 			}
-			retryRequest := zeroruntime.CompletionRequest{
-				Messages:        copyMessages(messages),
-				Tools:           exposed,
-				ReasoningEffort: options.ReasoningEffort,
-				PromptCacheKey:  options.SessionID,
-			}
+			retryPlan := planner.Plan(messages, exposed, options.ReasoningEffort)
+			retryRequest := retryPlan.Request
+			recordContextPlan(options, retryPlan)
 			retryStream, retryErr := streamWithReconnect(ctx, provider, retryRequest, reconnectNoticeFor(options))
 			if retryErr != nil {
 				result.Messages = copyMessages(messages)
@@ -698,7 +674,7 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 			}
 			options.Trace.Counter(trace.CounterToolCalls, 1)
 			recordOutputBudgetTrace(options.Trace, toolResult)
-			task.observe(taskStateEvent{kind: taskStateEventToolResult, toolResult: toolResult})
+			task.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: call.Arguments, toolResult: toolResult})
 			if options.OnToolResult != nil {
 				options.OnToolResult(toolResult)
 			}
@@ -712,9 +688,11 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 				turnRequestedModel = toolResult.RequestedModel
 			}
 			messages = append(messages, zeroruntime.Message{
-				Role:       zeroruntime.MessageRoleTool,
-				Content:    toolResult.Output,
-				ToolCallID: toolResult.ToolCallID,
+				Role:         zeroruntime.MessageRoleTool,
+				Content:      toolResult.Output,
+				ToolCallID:   toolResult.ToolCallID,
+				IsError:      toolResult.Status == tools.StatusError,
+				ChangedFiles: append([]string(nil), toolResult.ChangedFiles...),
 			})
 			// Images ride a following USER message rather than the tool result
 			// above. Every provider drops images on a tool-role message —
@@ -920,7 +898,7 @@ func Run(ctx context.Context, prompt string, provider Provider, options Options)
 		})
 	}
 	finalExposed, _ := partitionToolsCached(registry, permissionMode, options, loaded, toolDefCache)
-	if answer, finalMessages, finishReason := finalAnswerAfterMaxTurns(ctx, provider, messages, finalExposed, options); strings.TrimSpace(answer) != "" {
+	if answer, finalMessages, finishReason := finalAnswerAfterMaxTurns(ctx, provider, planner, messages, finalExposed, options); strings.TrimSpace(answer) != "" {
 		result.FinalAnswer = answer
 		result.FinishReason = finishReason
 		result.Messages = copyMessages(finalMessages)
@@ -962,7 +940,32 @@ func recordOutputBudgetTrace(recorder *trace.Recorder, result ToolResult) {
 	})
 }
 
-func finalAnswerAfterMaxTurns(ctx context.Context, provider Provider, messages []zeroruntime.Message, toolDefs []zeroruntime.ToolDefinition, options Options) (string, []zeroruntime.Message, string) {
+func recordContextPlan(options Options, plan contextPlan) {
+	recordContextPlanTrace(options.Trace, plan)
+	if options.OnContext != nil {
+		options.OnContext(plan.Breakdown)
+	}
+}
+
+func recordContextPlanTrace(recorder *trace.Recorder, plan contextPlan) {
+	if recorder == nil {
+		return
+	}
+	fingerprint := plan.PrefixFingerprint
+	recorder.EmitPrefixHash(trace.PrefixHash{
+		SystemPromptHash:       fingerprint.SystemPromptHash,
+		BaseInstructionsHash:   fingerprint.BaseInstructionsHash,
+		ConfirmationPolicyHash: fingerprint.ConfirmationPolicyHash,
+		ProjectContextHash:     fingerprint.ProjectContextHash,
+		SkillsHash:             fingerprint.SkillsHash,
+		ToolsHash:              fingerprint.ToolsHash,
+		SchemaHash:             fingerprint.SchemaHash,
+		CompletePrefixHash:     fingerprint.CompletePrefixHash,
+		InvalidationReason:     plan.Breakdown.PrefixInvalidationReason,
+	})
+}
+
+func finalAnswerAfterMaxTurns(ctx context.Context, provider Provider, planner *contextPlanner, messages []zeroruntime.Message, toolDefs []zeroruntime.ToolDefinition, options Options) (string, []zeroruntime.Message, string) {
 	finalMessages := copyMessages(messages)
 	finalMessages = append(finalMessages, zeroruntime.Message{
 		Role:    zeroruntime.MessageRoleUser,
@@ -971,12 +974,9 @@ func finalAnswerAfterMaxTurns(ctx context.Context, provider Provider, messages [
 	// The max-turns final-answer call is a pre-content connect, often after a long
 	// autonomous/cron run — route it through the reconnect helper so a single
 	// transient hiccup doesn't drop the final summary (AUDIT-L1).
-	stream, err := streamWithReconnect(ctx, provider, zeroruntime.CompletionRequest{
-		Messages:        copyMessages(finalMessages),
-		Tools:           toolDefs,
-		ReasoningEffort: options.ReasoningEffort,
-		PromptCacheKey:  options.SessionID,
-	}, reconnectNoticeFor(options))
+	plan := planner.Plan(finalMessages, toolDefs, options.ReasoningEffort)
+	recordContextPlan(options, plan)
+	stream, err := streamWithReconnect(ctx, provider, plan.Request, reconnectNoticeFor(options))
 	if err != nil {
 		return "", messages, ""
 	}
@@ -2718,9 +2718,36 @@ func permissionRequestFromEvent(event PermissionEvent, args map[string]any, opti
 		Grant:              event.Grant,
 		CommandPrefix:      append([]string(nil), event.CommandPrefix...),
 		AvailableDecisions: availablePermissionDecisions(event, args, options),
+		// Computed from the SAME conditions shellExecutionArgsForApproval uses,
+		// so the prompt cannot claim an escalation that will not happen or stay
+		// silent about one that will. Keeping the two in step matters more than
+		// the wording: a label that overstates gets ignored, and one that
+		// understates is the bug being fixed.
+		PrefixApprovalEscalates: shellPrefixApprovalEscalates(event.ToolName, args, options),
 	}
 }
 
+// shellPrefixApprovalEscalates reports whether approving a command prefix would
+// also take this command out of the sandbox.
+//
+// Deliberately mirrors shellExecutionArgsForApproval's guards rather than
+// re-deriving them: same tool test, same sandbox availability test, and the same
+// two opt-outs for a call that already asked for additional permissions or
+// escalation. Those already carry their own disclosure, so labelling them again
+// would be noise.
+func shellPrefixApprovalEscalates(toolName string, args map[string]any, options Options) bool {
+	if !isShellCommandTool(toolName) {
+		return false
+	}
+	if options.Sandbox == nil || !options.Sandbox.UnsandboxedExecutionAllowed() {
+		return false
+	}
+	if shellCommandAdditionalPermissionsRequested(args) || shellCommandRequiresEscalated(args) {
+		return false
+	}
+	return true
+}
+
 func availablePermissionDecisions(event PermissionEvent, args map[string]any, options Options) []PermissionDecisionAction {
 	if event.Action != PermissionActionPrompt {
 		return nil
@@ -3278,6 +3305,7 @@ func appendAbortedToolResults(messages []Message, remaining []ToolCall) []Messag
 			Role:       zeroruntime.MessageRoleTool,
 			Content:    abortedToolResultNotice,
 			ToolCallID: call.ID,
+			IsError:    true,
 		})
 	}
 	return messages
@@ -3308,6 +3336,9 @@ func copyMessages(messages []Message) []Message {
 		if message.Reasoning != nil {
 			copied[index].Reasoning = append([]zeroruntime.ReasoningBlock{}, message.Reasoning...)
 		}
+		if message.ChangedFiles != nil {
+			copied[index].ChangedFiles = append([]string(nil), message.ChangedFiles...)
+		}
 		// Deep-copy image attachments (slice AND each Data byte slice) so the
 		// raw image bytes are never aliased across history/request/result copies.
 		copied[index].Images = zeroruntime.CloneImageBlocks(message.Images)

internal/agent/loop_test.go

@@ -3592,6 +3592,11 @@ func TestRunAppendsAbortedPlaceholderForUnexecutedToolCallsOnGuardStop(t *testin
 	if !strings.Contains(strings.ToLower(placeholder), "aborted") {
 		t.Fatalf("expected the placeholder result to mark the call as aborted, got %q", placeholder)
 	}
+	for _, message := range result.Messages {
+		if message.ToolCallID == "flaky-2" && !message.IsError {
+			t.Fatalf("aborted placeholder must carry error status: %#v", message)
+		}
+	}
 
 	// Every tool_use in the final assistant message must have a matching result.
 	for _, message := range result.Messages {
@@ -3606,6 +3611,33 @@ func TestRunAppendsAbortedPlaceholderForUnexecutedToolCallsOnGuardStop(t *testin
 	}
 }
 
+func TestRunCarriesToolErrorStatusIntoMessageHistory(t *testing.T) {
+	registry := tools.NewRegistry()
+	registry.Register(alwaysFailingTool{})
+	provider := &mockProvider{turns: [][]zeroruntime.StreamEvent{
+		{
+			{Type: zeroruntime.StreamEventToolCallStart, ToolCallID: "failed-call", ToolName: "flaky"},
+			{Type: zeroruntime.StreamEventToolCallEnd, ToolCallID: "failed-call"},
+			{Type: zeroruntime.StreamEventDone},
+		},
+		{{Type: zeroruntime.StreamEventText, Content: "done"}, {Type: zeroruntime.StreamEventDone}},
+	}}
+
+	result, err := Run(context.Background(), "go", provider, Options{Registry: registry})
+	if err != nil {
+		t.Fatal(err)
+	}
+	for _, message := range result.Messages {
+		if message.ToolCallID == "failed-call" {
+			if !message.IsError {
+				t.Fatalf("failed tool result lost its structured status: %#v", message)
+			}
+			return
+		}
+	}
+	t.Fatalf("failed tool result missing from message history: %#v", result.Messages)
+}
+
 type secretEmittingTool struct{ output string }
 
 func (t secretEmittingTool) Name() string        { return "leak" }
@@ -3697,6 +3729,8 @@ func TestRunTracingWrapperStampsUsage(t *testing.T) {
 		{Type: zeroruntime.StreamEventDone},
 	}}}
 	onUsageCalls := 0
+	onContextCalls := 0
+	var contextPlan ContextBreakdown
 	rec := trace.NewRecorder("tracing-session", "run-1", "test")
 	if _, err := Run(context.Background(), "hi", provider, Options{
 		SessionID:    "tracing-session",
@@ -3705,6 +3739,10 @@ func TestRunTracingWrapperStampsUsage(t *testing.T) {
 		Model:        "test-model",
 		Trace:        rec,
 		OnUsage:      func(Usage) { onUsageCalls++ },
+		OnContext: func(breakdown ContextBreakdown) {
+			onContextCalls++
+			contextPlan = breakdown
+		},
 	}); err != nil {
 		t.Fatalf("Run: %v", err)
 	}
@@ -3731,6 +3769,12 @@ func TestRunTracingWrapperStampsUsage(t *testing.T) {
 	if onUsageCalls == 0 {
 		t.Fatal("wrapped OnUsage did not forward to the caller's callback")
 	}
+	if onContextCalls != 1 || len(contextPlan.Blocks) != 2 || contextPlan.PrefixInvalidationReason != "initial" {
+		t.Fatalf("context plan callback = calls %d, plan %#v", onContextCalls, contextPlan)
+	}
+	if len(tr.PrefixHashes) != 1 || tr.PrefixHashes[0].InvalidationReason != "initial" || tr.PrefixHashes[0].CompletePrefixHash != contextPlan.CompletePrefixHash {
+		t.Fatalf("trace context evidence = %#v, plan %#v", tr.PrefixHashes, contextPlan)
+	}
 }
 
 // TestRunNilTraceForwardsUsage verifies a nil recorder leaves the loop

internal/agent/prefix_escalation_disclosure_test.go

@@ -0,0 +1,118 @@
+package agent
+
+import (
+	"path/filepath"
+	"testing"
+
+	"github.com/Gitlawb/zero/internal/sandbox"
+	"github.com/Gitlawb/zero/internal/tools"
+)
+
+// escalatingEngine allows unsandboxed escalation: no denied reads, so
+// UnsandboxedExecutionAllowed is true and a prefix approval would rewrite the
+// call to require_escalated.
+func escalatingEngine(t *testing.T) *sandbox.Engine {
+	t.Helper()
+	policy := sandbox.DefaultPolicy()
+	policy.DenyRead = nil
+	return sandbox.NewEngine(sandbox.EngineOptions{WorkspaceRoot: t.TempDir(), Policy: policy})
+}
+
+// nonEscalatingEngine has a denied read, which is exactly the condition under
+// which escalation is refused, so no disclosure should be made.
+func nonEscalatingEngine(t *testing.T) *sandbox.Engine {
+	t.Helper()
+	root := t.TempDir()
+	policy := sandbox.DefaultPolicy()
+	policy.DenyRead = []string{filepath.Join(root, "secret.txt")}
+	return sandbox.NewEngine(sandbox.EngineOptions{WorkspaceRoot: root, Policy: policy})
+}
+
+// THE POINT OF THE FILE. The prompt's disclosure and the args rewrite must
+// agree on every input, because the defect being fixed is precisely that the
+// two disagreed: the rewrite escalated out of the sandbox while the prompt said
+// only "allow command prefix for session".
+//
+// Asserting agreement rather than asserting each side's expected value is what
+// makes this hold up. If someone later widens or narrows the rewrite's guards
+// and forgets the flag, the two diverge here and this fails, which a pair of
+// independent expected-value tests would not catch.
+func TestPrefixEscalationDisclosureMatchesTheArgsRewrite(t *testing.T) {
+	escalating := Options{Sandbox: escalatingEngine(t)}
+	denied := Options{Sandbox: nonEscalatingEngine(t)}
+
+	cases := []struct {
+		name     string
+		toolName string
+		args     map[string]any
+		options  Options
+	}{
+		{"plain bash command", "bash", map[string]any{"command": "go test ./..."}, escalating},
+		{"plain exec_command", "exec_command", map[string]any{"cmd": "go build ./..."}, escalating},
+		{"not a shell tool", "read_file", map[string]any{"path": "go.mod"}, escalating},
+		{"no sandbox configured", "bash", map[string]any{"command": "go test ./..."}, Options{}},
+		{"escalation refused by denied reads", "bash", map[string]any{"command": "go test ./..."}, denied},
+		{
+			"call already asks for escalation",
+			"bash",
+			map[string]any{"command": "go test ./...", "sandbox_permissions": string(tools.SandboxPermissionsRequireEscalated)},
+			escalating,
+		},
+		{
+			"call already asks for additional permissions",
+			"bash",
+			map[string]any{"command": "go test ./...", "sandbox_permissions": string(tools.SandboxPermissionsWithAdditionalPermissions)},
+			escalating,
+		},
+		// An unrecognized value is NOT an opt-out: the rewrite overwrites it, so
+		// the disclosure has to fire. Included because the obvious reading of
+		// the guards says otherwise, and a case asserting the wrong thing here
+		// would have passed silently.
+		{
+			"unrecognized sandbox_permissions value",
+			"bash",
+			map[string]any{"command": "go test ./...", "sandbox_permissions": "all"},
+			escalating,
+		},
+		{"empty args", "bash", map[string]any{}, escalating},
+		{"nil args", "bash", nil, escalating},
+	}
+
+	for _, testCase := range cases {
+		t.Run(testCase.name, func(t *testing.T) {
+			disclosed := shellPrefixApprovalEscalates(testCase.toolName, testCase.args, testCase.options)
+
+			// What the user's approval would actually be turned into.
+			rewritten := shellExecutionArgsForApproval(testCase.toolName, testCase.args, PermissionDecisionAllowPrefix, testCase.options)
+			escalates := shellCommandRequiresEscalated(rewritten) && !shellCommandRequiresEscalated(testCase.args)
+
+			if disclosed != escalates {
+				t.Fatalf("prompt discloses escalation=%v but approving actually escalates=%v; the prompt and the rewrite disagree, which is the consent gap this guards", disclosed, escalates)
+			}
+		})
+	}
+}
+
+// The two prefix decisions are the only ones that escalate, so a disclosure
+// attached to a request offering neither would be a false alarm. Checked
+// against the same predicate the rewrite consults.
+func TestOnlyPrefixDecisionsEscalate(t *testing.T) {
+	escalating := map[PermissionDecisionAction]bool{
+		PermissionDecisionAllowPrefix:       true,
+		PermissionDecisionAlwaysAllowPrefix: true,
+	}
+	for _, action := range []PermissionDecisionAction{
+		PermissionDecisionAllow,
+		PermissionDecisionAllowStrict,
+		PermissionDecisionAllowForSession,
+		PermissionDecisionAllowPrefix,
+		PermissionDecisionAlwaysAllowPrefix,
+		PermissionDecisionAlwaysAllow,
+		PermissionDecisionDeny,
+		PermissionDecisionCancel,
+	} {
+		if got := shellPrefixApprovalBypassesSandbox(action); got != escalating[action] {
+			t.Errorf("decision %q bypasses sandbox=%v, want %v", action, got, escalating[action])
+		}
+	}
+}

internal/agent/task_state.go

@@ -1,10 +1,14 @@
 package agent
 
 import (
+	"crypto/sha256"
 	"encoding/json"
+	"fmt"
 	"reflect"
+	"regexp"
 	"sort"
 	"strings"
+	"unicode/utf8"
 
 	"github.com/Gitlawb/zero/internal/tools"
 	"github.com/Gitlawb/zero/internal/trace"
@@ -52,17 +56,41 @@ type taskVerificationState struct {
 	LastOutcome Outcome `json:"last_outcome,omitempty"`
 }
 
+type taskFailureState struct {
+	Key     string `json:"key,omitempty"`
+	Tool    string `json:"tool"`
+	Command string `json:"command,omitempty"`
+	Summary string `json:"summary"`
+}
+
+type taskApprovalState struct {
+	Tool     string                   `json:"tool"`
+	Decision PermissionDecisionAction `json:"decision,omitempty"`
+	Scope    string                   `json:"scope,omitempty"`
+	Reason   string                   `json:"reason,omitempty"`
+}
+
+type taskArtifactState struct {
+	Tool string `json:"tool"`
+	Path string `json:"path"`
+}
+
 type taskStateSnapshot struct {
-	Revision           int                   `json:"revision"`
-	Objective          string                `json:"objective"`
-	Status             taskStatus            `json:"status"`
-	Plan               taskPlanState         `json:"plan"`
-	Tools              taskToolState         `json:"tools"`
-	Verification       taskVerificationState `json:"verification"`
-	ChangedFiles       []string              `json:"changed_files,omitempty"`
-	CompletionDecision CompletionDecision    `json:"completion_decision,omitempty"`
-	CompletionReason   string                `json:"completion_reason,omitempty"`
-	PlanParity         taskPlanParity        `json:"plan_parity"`
+	Revision            int                   `json:"revision"`
+	Objective           string                `json:"objective"`
+	Status              taskStatus            `json:"status"`
+	Plan                taskPlanState         `json:"plan"`
+	Tools               taskToolState         `json:"tools"`
+	Verification        taskVerificationState `json:"verification"`
+	ChangedFiles        []string              `json:"changed_files,omitempty"`
+	Constraints         []string              `json:"constraints,omitempty"`
+	UnresolvedFailures  []taskFailureState    `json:"unresolved_failures,omitempty"`
+	Approvals           []taskApprovalState   `json:"approvals,omitempty"`
+	Artifacts           []taskArtifactState   `json:"artifacts,omitempty"`
+	ResolvedFailureKeys []string              `json:"-"`
+	CompletionDecision  CompletionDecision    `json:"completion_decision,omitempty"`
+	CompletionReason    string                `json:"completion_reason,omitempty"`
+	PlanParity          taskPlanParity        `json:"plan_parity"`
 }
 
 type taskStateEventKind int
@@ -72,6 +100,7 @@ const (
 	taskStateEventToolResult
 	taskStateEventVerification
 	taskStateEventCompletion
+	taskStateEventPermission
 )
 
 type taskStateEvent struct {
@@ -80,6 +109,7 @@ type taskStateEvent struct {
 	toolResult   ToolResult
 	verification Outcome
 	completion   completionEvaluation
+	permission   PermissionEvent
 }
 
 // taskState is a deterministic projection of facts the loop already observes.
@@ -101,6 +131,7 @@ func newTaskState(objective string, recorder *trace.Recorder) *taskState {
 		},
 		changedFiles: map[string]struct{}{},
 	}
+	state.snapshotValue.Constraints = extractExplicitConstraints(objective)
 	state.recorder = recorder
 	return state
 }
@@ -134,6 +165,7 @@ func (state *taskState) observe(event taskStateEvent) bool {
 			}
 		}
 		state.snapshotValue.ChangedFiles = sortedKeys(state.changedFiles)
+		state.observeToolEvidence(event.arguments, event.toolResult)
 		changed = true
 	case taskStateEventVerification:
 		if event.verification == OutcomeDisabled {
@@ -160,6 +192,10 @@ func (state *taskState) observe(event taskStateEvent) bool {
 			state.snapshotValue.Status = taskStatusActive
 		}
 		changed = true
+	case taskStateEventPermission:
+		state.markActive()
+		state.observePermission(event.permission)
+		changed = true
 	}
 	if changed {
 		state.snapshotValue.Revision++
@@ -183,9 +219,180 @@ func (state *taskState) snapshot() taskStateSnapshot {
 	snapshot := state.snapshotValue
 	snapshot.Plan.Items = append([]taskPlanItem(nil), state.snapshotValue.Plan.Items...)
 	snapshot.ChangedFiles = append([]string(nil), state.snapshotValue.ChangedFiles...)
+	snapshot.Constraints = append([]string(nil), state.snapshotValue.Constraints...)
+	snapshot.UnresolvedFailures = append([]taskFailureState(nil), state.snapshotValue.UnresolvedFailures...)
+	snapshot.Approvals = append([]taskApprovalState(nil), state.snapshotValue.Approvals...)
+	snapshot.Artifacts = append([]taskArtifactState(nil), state.snapshotValue.Artifacts...)
+	snapshot.ResolvedFailureKeys = append([]string(nil), state.snapshotValue.ResolvedFailureKeys...)
 	return snapshot
 }
 
+const (
+	maxTaskEvidenceEntries = 8
+	maxTaskEvidenceBytes   = 320
+	maxTaskConstraints     = 10
+)
+
+func (state *taskState) observeToolEvidence(arguments string, result ToolResult) {
+	command := capTaskEvidence(commandFromArguments(arguments))
+	key := taskFailureKey(result.Name, command, arguments)
+	if result.Status == tools.StatusOK {
+		if hasTaskFailure(state.snapshotValue.UnresolvedFailures, key) {
+			state.snapshotValue.UnresolvedFailures = removeTaskFailure(state.snapshotValue.UnresolvedFailures, key)
+			state.snapshotValue.ResolvedFailureKeys = appendBoundedUnique(state.snapshotValue.ResolvedFailureKeys, key, maxTaskEvidenceEntries)
+		}
+	} else {
+		state.snapshotValue.ResolvedFailureKeys = removeString(state.snapshotValue.ResolvedFailureKeys, key)
+		state.snapshotValue.UnresolvedFailures = removeTaskFailure(state.snapshotValue.UnresolvedFailures, key)
+		state.snapshotValue.UnresolvedFailures = appendBounded(state.snapshotValue.UnresolvedFailures, taskFailureState{
+			Key: key, Tool: result.Name, Command: command, Summary: capTaskEvidence(firstLine(result.Output)),
+		}, maxTaskEvidenceEntries)
+	}
+	for _, metaKey := range []string{"spill_path", "artifact_path"} {
+		if path := strings.TrimSpace(result.Meta[metaKey]); path != "" {
+			state.snapshotValue.Artifacts = appendBoundedUnique(state.snapshotValue.Artifacts,
+				taskArtifactState{Tool: result.Name, Path: capTaskEvidence(path)}, maxTaskEvidenceEntries)
+		}
+	}
+}
+
+func taskFailureKey(toolName, command, arguments string) string {
+	identity := command
+	if identity == "" {
+		canonical := []byte(strings.TrimSpace(arguments))
+		var value any
+		if json.Unmarshal(canonical, &value) == nil {
+			if encoded, err := json.Marshal(value); err == nil {
+				canonical = encoded
+			}
+		}
+		digest := sha256.Sum256(canonical)
+		identity = fmt.Sprintf("args:%x", digest[:8])
+	}
+	return strings.TrimSpace(toolName) + "\x00" + identity
+}
+
+func (state *taskState) observePermission(event PermissionEvent) {
+	decision := event.DecisionAction
+	if decision == "" {
+		decision = PermissionDecisionAction(event.Action)
+	}
+	state.snapshotValue.Approvals = appendBoundedUnique(state.snapshotValue.Approvals, taskApprovalState{
+		Tool: event.ToolName, Decision: decision, Scope: capTaskEvidence(event.Scope),
+		Reason: capTaskEvidence(firstNonEmptyString(event.DecisionReason, event.Reason)),
+	}, maxTaskEvidenceEntries)
+}
+
+func commandFromArguments(arguments string) string {
+	var object map[string]json.RawMessage
+	if json.Unmarshal([]byte(strings.TrimSpace(arguments)), &object) != nil {
+		return ""
+	}
+	for _, key := range []string{"cmd", "command", "script", "shell"} {
+		var command string
+		if raw, ok := object[key]; ok && json.Unmarshal(raw, &command) == nil {
+			return strings.TrimSpace(command)
+		}
+	}
+	return ""
+}
+
+func firstLine(value string) string {
+	value = strings.TrimSpace(value)
+	if index := strings.IndexByte(value, '\n'); index >= 0 {
+		value = value[:index]
+	}
+	return value
+}
+
+func capTaskEvidence(value string) string {
+	value = strings.TrimSpace(value)
+	if len(value) <= maxTaskEvidenceBytes {
+		return value
+	}
+	limit := maxTaskEvidenceBytes - 3
+	for limit > 0 && !utf8.RuneStart(value[limit]) {
+		limit--
+	}
+	return strings.TrimSpace(value[:limit]) + "..."
+}
+
+var explicitConstraintPatterns = []*regexp.Regexp{
+	regexp.MustCompile(`(?i)\bprefer(?:s|red|ring)?\s+\w`),
+	regexp.MustCompile(`(?i)\bdon'?t want\b`),
+	regexp.MustCompile(`(?i)\balways (?:use|do|run|prefer|keep|make|format|write|add|set|put|prefix|start|include|append)\b`),
+	regexp.MustCompile(`(?i)\bnever (?:use|do|run|push|commit|write|ignore|add|set|put|remove|delete|include|deploy)\b`),
+	regexp.MustCompile(`(?i)\bplease (?:use|avoid|keep|make|don'?t|do not|format|write)\b`),
+	regexp.MustCompile(`(?i)\b(?:style|format|language|naming)\s*[:=]\s*\S`),
+}
+
+func extractExplicitConstraints(text string) []string {
+	var constraints []string
+	for _, line := range strings.Split(text, "\n") {
+		line = strings.TrimSpace(line)
+		if len(line) < 5 || len(line) > 200 || strings.HasSuffix(line, "?") || strings.Contains(line, "?...") {
+			continue
+		}
+		for _, pattern := range explicitConstraintPatterns {
+			if pattern.MatchString(line) {
+				constraints = appendBoundedUnique(constraints, line, maxTaskConstraints)
+				break
+			}
+		}
+		if len(constraints) == maxTaskConstraints {
+			break
+		}
+	}
+	return constraints
+}
+
+func appendBounded[T any](values []T, value T, limit int) []T {
+	values = append(values, value)
+	if len(values) > limit {
+		values = values[len(values)-limit:]
+	}
+	return values
+}
+
+func appendBoundedUnique[T comparable](values []T, value T, limit int) []T {
+	filtered := values[:0]
+	for _, existing := range values {
+		if existing != value {
+			filtered = append(filtered, existing)
+		}
+	}
+	return appendBounded(filtered, value, limit)
+}
+
+func hasTaskFailure(values []taskFailureState, key string) bool {
+	for _, value := range values {
+		if value.Key == key {
+			return true
+		}
+	}
+	return false
+}
+
+func removeTaskFailure(values []taskFailureState, key string) []taskFailureState {
+	out := values[:0]
+	for _, value := range values {
+		if value.Key != key {
+			out = append(out, value)
+		}
+	}
+	return out
+}
+
+func removeString(values []string, target string) []string {
+	out := make([]string, 0, len(values))
+	for _, value := range values {
+		if value != target {
+			out = append(out, value)
+		}
+	}
+	return out
+}
+
 // observePlanParity compares only the latest plan projection with the plan tool
 // calls still present in messages. It mutates the snapshot and emits when the
 // parity value changes; objective, tool, and verification fields are not part of

internal/agent/task_state_test.go

@@ -115,6 +115,68 @@ func TestTaskStateSnapshotIsImmutable(t *testing.T) {
 	}
 }
 
+func TestTaskStateRecordsDurableRuntimeEvidence(t *testing.T) {
+	state := newTaskState("Please keep the change focused.\nNever commit generated reports.", nil)
+	arguments := `{"cmd":"go test ./internal/agent"}`
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: arguments, toolResult: ToolResult{
+		ToolCallID: "test-1", Name: "exec_command", Status: tools.StatusError,
+		Output: "Error: TestResumeRetainsState failed\nfull diagnostic",
+		Meta:   map[string]string{"spill_path": ".zero/artifacts/test-1.txt"},
+	}})
+	state.observe(taskStateEvent{kind: taskStateEventPermission, permission: PermissionEvent{
+		ToolName: "exec_command", DecisionAction: PermissionDecisionAllowForSession,
+		Scope: "/tmp", DecisionReason: "write a temporary fixture",
+	}})
+
+	snapshot := state.snapshot()
+	if !reflect.DeepEqual(snapshot.Constraints, []string{"Please keep the change focused.", "Never commit generated reports."}) {
+		t.Fatalf("unexpected explicit constraints: %#v", snapshot.Constraints)
+	}
+	if len(snapshot.UnresolvedFailures) != 1 || snapshot.UnresolvedFailures[0].Command != "go test ./internal/agent" || snapshot.UnresolvedFailures[0].Summary != "Error: TestResumeRetainsState failed" {
+		t.Fatalf("unexpected failure evidence: %#v", snapshot.UnresolvedFailures)
+	}
+	if len(snapshot.Artifacts) != 1 || snapshot.Artifacts[0].Path != ".zero/artifacts/test-1.txt" {
+		t.Fatalf("unexpected artifact evidence: %#v", snapshot.Artifacts)
+	}
+	if len(snapshot.Approvals) != 1 || snapshot.Approvals[0].Decision != PermissionDecisionAllowForSession || snapshot.Approvals[0].Scope != "/tmp" {
+		t.Fatalf("unexpected approval evidence: %#v", snapshot.Approvals)
+	}
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"path":"a.go"}`, toolResult: ToolResult{
+		ToolCallID: "read-a", Name: "read_file", Status: tools.StatusError, Output: "Error: a.go is unavailable",
+	}})
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"path":"b.go"}`, toolResult: ToolResult{
+		ToolCallID: "read-b", Name: "read_file", Status: tools.StatusOK, Output: "package b",
+	}})
+	if failures := state.snapshot().UnresolvedFailures; len(failures) != 2 || failures[1].Summary != "Error: a.go is unavailable" {
+		t.Fatalf("success for a different target resolved the wrong failure: %#v", failures)
+	}
+
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: arguments, toolResult: ToolResult{
+		ToolCallID: "test-2", Name: "exec_command", Status: tools.StatusOK, Output: "ok",
+	}})
+	if failures := state.snapshot().UnresolvedFailures; len(failures) != 1 || failures[0].Summary != "Error: a.go is unavailable" {
+		t.Fatalf("successful retry did not resolve only its matching failure: %#v", failures)
+	}
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"path":"a.go"}`, toolResult: ToolResult{
+		ToolCallID: "read-a-2", Name: "read_file", Status: tools.StatusOK, Output: "package a",
+	}})
+	if failures := state.snapshot().UnresolvedFailures; len(failures) != 0 {
+		t.Fatalf("successful non-command retry did not resolve its matching failure: %#v", failures)
+	}
+	state.observe(taskStateEvent{kind: taskStateEventToolResult, arguments: `{"path":"a.go"}`, toolResult: ToolResult{
+		ToolCallID: "read-a-3", Name: "read_file", Status: tools.StatusError, Output: "Error: a.go failed again",
+	}})
+	snapshot = state.snapshot()
+	if len(snapshot.UnresolvedFailures) != 1 || snapshot.UnresolvedFailures[0].Summary != "Error: a.go failed again" {
+		t.Fatalf("a failure recurring after success was hidden: %#v", snapshot.UnresolvedFailures)
+	}
+	for _, key := range snapshot.ResolvedFailureKeys {
+		if key == snapshot.UnresolvedFailures[0].Key {
+			t.Fatalf("recurring failure retained a stale resolved key: %#v", snapshot.ResolvedFailureKeys)
+		}
+	}
+}
+
 func TestTaskStatePlanParityUsesLatestPlan(t *testing.T) {
 	state := newTaskState("objective", nil)
 	state.observe(taskStateEvent{kind: taskStateEventPlan, arguments: `{"plan":[{"content":"old","status":"completed"}]}`})

internal/agent/types.go

@@ -176,6 +176,22 @@ type PermissionRequest struct {
 	Grant              *sandbox.Grant             `json:"grant,omitempty"`
 	CommandPrefix      []string                   `json:"commandPrefix,omitempty"`
 	AvailableDecisions []PermissionDecisionAction `json:"availableDecisions,omitempty"`
+	// PrefixApprovalEscalates reports that approving a command prefix will also
+	// run the command OUTSIDE the sandbox, not merely stop asking about it.
+	//
+	// It exists because that consequence was real but invisible. Approving a
+	// prefix rewrites the call to sandbox_permissions: require_escalated, which
+	// resolves to a nil engine and genuinely unsandboxed execution, and the
+	// engine's own escalation prompt is then satisfied by the approval just
+	// given for the sandboxed form. So the operator authorized one thing and got
+	// a wider one, having been shown only "allow command prefix for session".
+	//
+	// The escalation itself is deliberate and guarded: proposedCommandPrefix
+	// refuses to offer a prefix while any other segment of the command is not
+	// known-safe, precisely so an unreviewed segment cannot ride out of the
+	// sandbox on it. What was missing was telling the person deciding, so this
+	// surfaces it rather than removing it.
+	PrefixApprovalEscalates bool `json:"prefixApprovalEscalates,omitempty"`
 }
 
 type PermissionDecision struct {
@@ -333,9 +349,11 @@ type Options struct {
 	// specialist child process emits while running. The toolCallID identifies
 	// which Task tool call the progress belongs to. nil is a no-op.
 	OnToolProgress func(toolCallID string, event streamjson.Event)
-	// OnContext, when set, is called once per turn with the per-category context
-	// budget of the request about to be sent, so a surface (TUI/CLI) can show
-	// context utilization. Opt-in like the other callbacks; nil is a no-op.
+	// OnContext, when set, is called for each main agent request with its
+	// per-category context budget, including a replacement request after
+	// compaction or a stall retry. Internal summarizer requests are excluded so
+	// surfaces keep showing the active conversation budget. Opt-in like the other
+	// callbacks; nil is a no-op.
 	OnContext func(ContextBreakdown)
 	// ModelSwitcher, when set, lets a tool escalate the run to a stronger model
 	// mid-run: the loop calls it with the requested model id and, on success,

internal/sessions/replay.go

@@ -7,6 +7,7 @@ import (
 	"unicode/utf8"
 
 	"github.com/Gitlawb/zero/internal/redaction"
+	"github.com/Gitlawb/zero/internal/zeroruntime"
 )
 
 type EventRef struct {
@@ -37,6 +38,7 @@ type RewindPlan struct {
 type CompactionOptions struct {
 	PreserveLast   int
 	MaxPromptChars int
+	SkipPrompt     bool
 }
 
 type CompactionPlan struct {
@@ -47,8 +49,9 @@ type CompactionPlan struct {
 	CompactableEvents []EventRef `json:"compactableEvents"`
 	PreservedEvents   []EventRef `json:"preservedEvents"`
 	SummaryPrompt     string     `json:"summaryPrompt"`
-	PromptChars       int        `json:"promptChars"`
-	Truncated         bool       `json:"truncated,omitempty"`
+	// PromptChars counts prompt text content and excludes provider protocol framing.
+	PromptChars int  `json:"promptChars"`
+	Truncated   bool `json:"truncated,omitempty"`
 }
 
 type RecordCompactionInput struct {
@@ -164,7 +167,11 @@ func (store *Store) PlanCompaction(sessionID string, options CompactionOptions)
 	}
 	compactable := events[:split]
 	preserved := events[split:]
-	prompt, truncated := buildCompactionPrompt(compactable, maxPromptChars)
+	prompt := ""
+	truncated := false
+	if !options.SkipPrompt {
+		prompt, truncated = buildCompactionPrompt(compactable, maxPromptChars)
+	}
 	return CompactionPlan{
 		SessionID:         sessionID,
 		PreserveLast:      preserveLast,
@@ -312,6 +319,88 @@ func buildCompactionPrompt(events []Event, maxChars int) (string, bool) {
 	return prompt, false
 }
 
+// CompactionMessages converts durable session events into the same normalized
+// message shape used by the running agent's compaction pipeline. Provider usage
+// and checkpoint blobs are omitted. Message/tool fields rely on the session
+// writer's invariant that tool output is scrubbed before persistence;
+// ask_user answers and generic event previews are redacted here.
+func CompactionMessages(events []Event) []zeroruntime.Message {
+	messages := make([]zeroruntime.Message, 0, len(events))
+	for _, event := range events {
+		var payload map[string]any
+		_ = json.Unmarshal(event.Payload, &payload)
+		stringField := func(key string) string {
+			value, _ := payload[key].(string)
+			return strings.TrimSpace(value)
+		}
+		switch event.Type {
+		case EventMessage:
+			role := strings.ToLower(stringField("role"))
+			content := stringField("content")
+			switch role {
+			case "user":
+				messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: content})
+			case "assistant":
+				messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, Content: content})
+			case "ask_user_answers":
+				if answers, ok := payload["answers"]; ok {
+					encoded, _ := json.Marshal(answers)
+					messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "User answers: " + redaction.RedactString(string(encoded), redaction.Options{})})
+				}
+			default:
+				if content != "" {
+					messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: content})
+				}
+			}
+		case EventToolCall:
+			messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleAssistant, ToolCalls: []zeroruntime.ToolCall{{
+				ID: firstSessionString(stringField("toolCallId"), stringField("id")), Name: firstSessionString(stringField("name"), stringField("toolName")), Arguments: stringField("arguments"),
+			}}})
+		case EventToolResult:
+			status := strings.ToLower(stringField("status"))
+			messages = append(messages, zeroruntime.Message{
+				Role: zeroruntime.MessageRoleTool, ToolCallID: firstSessionString(stringField("toolCallId"), stringField("id")),
+				Content: stringField("output"), IsError: status != "" && status != "ok", ChangedFiles: sessionStringSlice(payload["changedFiles"]),
+			})
+		case EventCompaction:
+			if summary := stringField("summary"); summary != "" {
+				messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: "[Summary of earlier conversation]\n" + summary})
+			}
+		case EventProviderUsage, EventSessionCheckpoint:
+			continue
+		default:
+			preview := shapedPayloadPreview(event)
+			if strings.TrimSpace(preview) != "" && preview != "{}" {
+				messages = append(messages, zeroruntime.Message{Role: zeroruntime.MessageRoleUser, Content: fmt.Sprintf("[%s] %s", event.Type, preview)})
+			}
+		}
+	}
+	return messages
+}
+
+func firstSessionString(values ...string) string {
+	for _, value := range values {
+		if strings.TrimSpace(value) != "" {
+			return strings.TrimSpace(value)
+		}
+	}
+	return ""
+}
+
+func sessionStringSlice(value any) []string {
+	raw, ok := value.([]any)
+	if !ok {
+		return nil
+	}
+	values := make([]string, 0, len(raw))
+	for _, item := range raw {
+		if text, ok := item.(string); ok && strings.TrimSpace(text) != "" {
+			values = append(values, strings.TrimSpace(text))
+		}
+	}
+	return values
+}
+
 func shapedPayloadPreview(event Event) string {
 	switch event.Type {
 	case EventPermission, EventPermissionRequest, EventPermissionDecision:

internal/sessions/replay_test.go

@@ -5,8 +5,27 @@ import (
 	"strings"
 	"testing"
 	"time"
+
+	"github.com/Gitlawb/zero/internal/zeroruntime"
 )
 
+func TestCompactionMessagesPreservesInteractiveAndMutationEvidence(t *testing.T) {
+	events := []Event{
+		{Type: EventToolCall, Payload: json.RawMessage(`{"id":"ask","name":"ask_user","arguments":"{\"questions\":[{\"question\":\"Which database?\"}]}"}`)},
+		{Type: EventToolResult, Payload: json.RawMessage(`{"toolCallId":"ask","name":"ask_user","status":"ok","output":"Postgres only"}`)},
+		{Type: EventToolCall, Payload: json.RawMessage(`{"id":"patch","name":"apply_patch","arguments":"{\"patch\":\"*** Update File: db.go\"}"}`)},
+		{Type: EventToolResult, Payload: json.RawMessage(`{"toolCallId":"patch","name":"apply_patch","status":"ok","output":"Done!","changedFiles":["db.go"]}`)},
+	}
+
+	messages := CompactionMessages(events)
+	if len(messages) != 4 || messages[0].Role != zeroruntime.MessageRoleAssistant || messages[1].Role != zeroruntime.MessageRoleTool {
+		t.Fatalf("unexpected normalized compaction messages: %#v", messages)
+	}
+	if messages[1].Content != "Postgres only" || len(messages[3].ChangedFiles) != 1 || messages[3].ChangedFiles[0] != "db.go" {
+		t.Fatalf("interactive or mutation evidence was lost: %#v", messages)
+	}
+}
+
 func TestStorePlansRewindBySequence(t *testing.T) {
 	store := NewStore(StoreOptions{RootDir: t.TempDir(), Now: sequenceClock([]time.Time{
 		time.Date(2026, 6, 6, 10, 0, 0, 0, time.UTC),
@@ -130,6 +149,26 @@ func TestStorePlansCompactionWindow(t *testing.T) {
 	}
 }
 
+func TestStoreCanPlanCompactionWithoutBuildingLegacyPrompt(t *testing.T) {
+	store := NewStore(StoreOptions{RootDir: t.TempDir()})
+	session, err := store.Create(CreateInput{SessionID: "compactnoprompt"})
+	if err != nil {
+		t.Fatal(err)
+	}
+	for _, content := range []string{"one", "two", "three"} {
+		if _, err := store.AppendEvent(session.SessionID, AppendEventInput{Type: EventMessage, Payload: map[string]string{"content": content}}); err != nil {
+			t.Fatal(err)
+		}
+	}
+	plan, err := store.PlanCompaction(session.SessionID, CompactionOptions{PreserveLast: 1, SkipPrompt: true})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if plan.CompactableCount != 2 || plan.SummaryPrompt != "" || plan.PromptChars != 0 || plan.Truncated {
+		t.Fatalf("unexpected prompt-free plan: %#v", plan)
+	}
+}
+
 func TestStoreCompactionShapesSensitivePermissionEvents(t *testing.T) {
 	secret := "sk-proj-abcdefghijklmnopqrstuvwxyz"
 	store := NewStore(StoreOptions{RootDir: t.TempDir()})

internal/trace/emit.go

@@ -86,16 +86,16 @@ func WriteNDJSON(w io.Writer, t *TurnTrace) error {
 		}
 	}
 
-	// Prefix fingerprints are emitted after counters in insertion (turn)
+	// Prefix fingerprints are emitted after counters in insertion (request)
 	// order. The order is the order EmitPrefixHash was called, which is the
-	// order the agent loop computed each turn's fingerprint, which is the
-	// order a downstream consumer needs to correlate a prefix_hash event
-	// with the cached_input_tokens counter for that turn. Sorting by
-	// complete_prefix hash would destroy that correlation, so we do not
+	// order the agent computed each request's fingerprint, which is the
+	// order a downstream consumer needs to reconstruct prefix changes across
+	// main, compaction, and retry requests. Sorting by complete_prefix hash would
+	// destroy that sequence, so we do not
 	// sort. The slice is already a deep copy from Finish (see
 	// Recorder.Finish) so it is safe to range over without copying.
 	for _, p := range t.PrefixHashes {
-		if err := enc.Encode(map[string]any{
+		obj := map[string]any{
 			"type":                "prefix_hash",
 			"system_prompt":       p.SystemPromptHash,
 			"base_instructions":   p.BaseInstructionsHash,
@@ -105,7 +105,11 @@ func WriteNDJSON(w io.Writer, t *TurnTrace) error {
 			"tools":               p.ToolsHash,
 			"schema":              p.SchemaHash,
 			"complete_prefix":     p.CompletePrefixHash,
-		}); err != nil {
+		}
+		if p.InvalidationReason != "" {
+			obj["invalidation_reason"] = p.InvalidationReason
+		}
+		if err := enc.Encode(obj); err != nil {
 			return err
 		}
 	}

internal/trace/parse.go

@@ -116,6 +116,7 @@ func ReadNDJSON(r io.Reader) (*TurnTrace, error) {
 				ToolsHash:              stringField(obj, "tools"),
 				SchemaHash:             stringField(obj, "schema"),
 				CompletePrefixHash:     stringField(obj, "complete_prefix"),
+				InvalidationReason:     stringField(obj, "invalidation_reason"),
 			})
 		case "output_budget":
 			if !sawTraceHeader {

internal/trace/recorder.go

@@ -177,9 +177,9 @@ func (r *Recorder) StampFirstUsefulAction() {
 }
 
 // EmitPrefixHash records one prompt-prefix fingerprint on the trace. Multiple
-// calls are allowed within a run (one per turn, typically) and accumulate in
-// order. The first call after Finish is a no-op; later calls are also no-ops
-// because the trace has been sealed.
+// calls are allowed within a run (one per planned provider request) and
+// accumulate in request order. The first call after Finish is a no-op; later
+// calls are also no-ops because the trace has been sealed.
 func (r *Recorder) EmitPrefixHash(p PrefixHash) {
 	if r == nil {
 		return

internal/trace/trace.go

@@ -159,6 +159,7 @@ type PrefixHash struct {
 	ToolsHash              string `json:"tools"`
 	SchemaHash             string `json:"schema"`
 	CompletePrefixHash     string `json:"complete_prefix"`
+	InvalidationReason     string `json:"invalidation_reason,omitempty"`
 }
 
 // WallDuration is the total traced wall time of the run.

internal/trace/trace_test.go

@@ -382,6 +382,7 @@ func TestReadNDJSONRoundTrip(t *testing.T) {
 		ToolsHash:              "t1",
 		SchemaHash:             "x1",
 		CompletePrefixHash:     "complete1",
+		InvalidationReason:     "initial",
 	})
 	r.EmitPrefixHash(PrefixHash{
 		SystemPromptHash:       "system2",
@@ -392,6 +393,7 @@ func TestReadNDJSONRoundTrip(t *testing.T) {
 		ToolsHash:              "t2",
 		SchemaHash:             "x2",
 		CompletePrefixHash:     "complete2",
+		InvalidationReason:     "tools",
 	})
 	original := r.Finish()
 
@@ -421,8 +423,8 @@ func TestReadNDJSONRoundTrip(t *testing.T) {
 	if parsed.FirstTokenAt.IsZero() {
 		t.Fatal("first_token_at lost in round-trip")
 	}
-	// prefix_hash round-trip: two events, in insertion order, with all
-	// seven sub-hash fields preserved exactly.
+	// prefix_hash round-trip: two events, in insertion order, with all hash
+	// fields and the invalidation reason preserved exactly.
 	if len(parsed.PrefixHashes) != 2 {
 		t.Fatalf("expected 2 prefix_hash events after round-trip, got %d", len(parsed.PrefixHashes))
 	}
@@ -435,6 +437,38 @@ func TestReadNDJSONRoundTrip(t *testing.T) {
 	if parsed.PrefixHashes[1].SystemPromptHash != "system2" || parsed.PrefixHashes[1].BaseInstructionsHash != "b2" || parsed.PrefixHashes[1].SchemaHash != "x2" {
 		t.Fatalf("prefix_hash sub-hashes lost on second event: got %+v", parsed.PrefixHashes[1])
 	}
+	if parsed.PrefixHashes[0].InvalidationReason != "initial" || parsed.PrefixHashes[1].InvalidationReason != "tools" {
+		t.Fatalf("prefix invalidation reasons lost: %+v", parsed.PrefixHashes)
+	}
+}
+
+func TestWriteNDJSONOmitsEmptyPrefixInvalidationReason(t *testing.T) {
+	recorder := NewRecorder("session", "run", "test")
+	recorder.Start()
+	recorder.EmitPrefixHash(PrefixHash{CompletePrefixHash: "stable"})
+	tr := recorder.Finish()
+
+	var output bytes.Buffer
+	if err := WriteNDJSON(&output, tr); err != nil {
+		t.Fatalf("WriteNDJSON: %v", err)
+	}
+	found := false
+	for _, line := range strings.Split(strings.TrimSpace(output.String()), "\n") {
+		var event map[string]any
+		if err := json.Unmarshal([]byte(line), &event); err != nil {
+			t.Fatalf("decode event: %v", err)
+		}
+		if event["type"] != "prefix_hash" {
+			continue
+		}
+		found = true
+		if _, exists := event["invalidation_reason"]; exists {
+			t.Fatalf("empty invalidation reason should be omitted: %s", line)
+		}
+	}
+	if !found {
+		t.Fatal("prefix_hash event not written")
+	}
 }
 
 func TestReadNDJSONRejectsNonTrace(t *testing.T) {

internal/tui/permission_prompt.go

@@ -43,9 +43,9 @@ func permissionOptions(request agent.PermissionRequest) []permissionOption {
 		case agent.PermissionDecisionAllowForSession:
 			options = append(options, permissionOption{label: "allow for session", hotkey: "s", choice: permissionDecisionAllowForSession})
 		case agent.PermissionDecisionAllowPrefix:
-			options = append(options, permissionOption{label: "allow command prefix for session", hotkey: "p", choice: permissionDecisionAllowPrefix})
+			options = append(options, permissionOption{label: prefixApprovalLabel("allow command prefix for session", request), hotkey: "p", choice: permissionDecisionAllowPrefix})
 		case agent.PermissionDecisionAlwaysAllowPrefix:
-			options = append(options, permissionOption{label: "always allow command prefix", hotkey: "y", choice: permissionDecisionAlwaysAllowPrefix})
+			options = append(options, permissionOption{label: prefixApprovalLabel("always allow command prefix", request), hotkey: "y", choice: permissionDecisionAlwaysAllowPrefix})
 		case agent.PermissionDecisionAlwaysAllow:
 			options = append(options, permissionOption{label: "always", hotkey: "y", choice: permissionDecisionAlwaysAllow})
 		case agent.PermissionDecisionDeny:
@@ -155,3 +155,21 @@ func (m model) cancelPermissionTyping() (tea.Model, tea.Cmd) {
 	m.pendingPermission.savedDraft = ""
 	return m, nil
 }
+
+// prefixApprovalLabel spells out that approving a prefix also takes the command
+// out of the sandbox.
+//
+// Approving a prefix rewrites the call to require_escalated, which resolves to
+// unsandboxed execution, and the engine's escalation prompt is then satisfied by
+// the approval just given for the sandboxed form. The operator was shown only
+// "allow command prefix for session" and got something wider, which is a consent
+// gap rather than a bug in the escalation itself.
+//
+// Only appended when it is true. The backend computes that from the same guards
+// the rewrite uses, so a prompt that says this always means it.
+func prefixApprovalLabel(base string, request agent.PermissionRequest) string {
+	if !request.PrefixApprovalEscalates {
+		return base
+	}
+	return base + " (runs outside the sandbox)"
+}

internal/tui/permission_prompt_escalation_test.go

@@ -0,0 +1,70 @@
+package tui
+
+import (
+	"strings"
+	"testing"
+
+	"github.com/Gitlawb/zero/internal/agent"
+)
+
+func prefixOptionLabels(request agent.PermissionRequest) []string {
+	labels := []string{}
+	for _, option := range permissionOptions(request) {
+		if option.choice == permissionDecisionAllowPrefix || option.choice == permissionDecisionAlwaysAllowPrefix {
+			labels = append(labels, option.label)
+		}
+	}
+	return labels
+}
+
+func prefixRequest(escalates bool) agent.PermissionRequest {
+	return agent.PermissionRequest{
+		ToolName: "bash",
+		AvailableDecisions: []agent.PermissionDecisionAction{
+			agent.PermissionDecisionAllow,
+			agent.PermissionDecisionAllowPrefix,
+			agent.PermissionDecisionAlwaysAllowPrefix,
+			agent.PermissionDecisionDeny,
+		},
+		PrefixApprovalEscalates: escalates,
+	}
+}
+
+// Approving a prefix also runs the command outside the sandbox, and the label
+// is the only place the person deciding could learn that. Both prefix options
+// escalate, so both must say so; covering only one would leave the other as a
+// silent path to the same outcome.
+func TestPrefixOptionsDiscloseLeavingTheSandbox(t *testing.T) {
+	labels := prefixOptionLabels(prefixRequest(true))
+	if len(labels) != 2 {
+		t.Fatalf("expected both prefix options, got %#v", labels)
+	}
+	for _, label := range labels {
+		if !strings.Contains(label, "outside the sandbox") {
+			t.Errorf("prefix option %q does not say the command leaves the sandbox, so approving it is uninformed consent", label)
+		}
+	}
+}
+
+// The disclosure has to be conditional. When escalation will not happen, saying
+// it will is a false warning, and a prompt that cries wolf on every prefix is
+// one the user learns to ignore, which costs the disclosure its whole value.
+func TestPrefixOptionsStaySilentWhenNoEscalationHappens(t *testing.T) {
+	for _, label := range prefixOptionLabels(prefixRequest(false)) {
+		if strings.Contains(label, "sandbox") {
+			t.Errorf("prefix option %q warns about the sandbox when approving would not leave it", label)
+		}
+	}
+}
+
+// The non-prefix options do not escalate, so the flag must not bleed into them.
+func TestNonPrefixOptionsNeverCarryTheDisclosure(t *testing.T) {
+	for _, option := range permissionOptions(prefixRequest(true)) {
+		if option.choice == permissionDecisionAllowPrefix || option.choice == permissionDecisionAlwaysAllowPrefix {
+			continue
+		}
+		if strings.Contains(option.label, "sandbox") {
+			t.Errorf("option %q carries the prefix escalation disclosure but does not escalate", option.label)
+		}
+	}
+}

internal/tui/session_controls.go

@@ -21,7 +21,6 @@ import (
 var responseStyles = []string{"balanced", "concise", "explanatory", "review"}
 
 const tuiCompactionPreserveLast = 8
-const tuiCompactionMaxPromptChars = 8000
 const compactStatusRowID = "compact/status"
 
 var compactFrames = []string{"⠂", "⠒", "⠲", "⠴"}
@@ -842,8 +841,8 @@ func (m model) compactActiveSession() (model, CompactResult, error) {
 	beforeEvents := append([]sessions.Event{}, m.sessionEvents...)
 	beforeTokens := estimateTranscriptTokens(m.transcript)
 	plan, err := m.sessionStore.PlanCompaction(m.activeSession.SessionID, sessions.CompactionOptions{
-		PreserveLast:   tuiCompactionPreserveLast,
-		MaxPromptChars: tuiCompactionMaxPromptChars,
+		PreserveLast: tuiCompactionPreserveLast,
+		SkipPrompt:   true,
 	})
 	if err != nil {
 		return m, CompactResult{}, err
@@ -857,13 +856,26 @@ func (m model) compactActiveSession() (model, CompactResult, error) {
 		}, nil
 	}
 
-	summary, err := m.summarizeCompactionPlan(plan)
+	rawEvents, err := m.sessionStore.ReadEvents(m.activeSession.SessionID)
+	if err != nil {
+		return m, CompactResult{}, fmt.Errorf("read session events for compaction: %w", err)
+	}
+	compactableEvents, err := sessionEventsForRefs(rawEvents, plan.CompactableEvents)
 	if err != nil {
 		return m, CompactResult{}, err
 	}
+	summaryResult, err := m.summarizeCompactionPlan(plan, sessions.CompactionMessages(compactableEvents))
+	if err != nil {
+		return m, CompactResult{}, err
+	}
+	// PromptChars counts the text content sent to the provider: the shared
+	// system instruction plus projected message/tool payloads. Provider protocol
+	// framing is intentionally excluded.
+	plan.PromptChars = len(agent.CompactionSummaryInstructions) + summaryResult.ProjectedChars
+	plan.Truncated = summaryResult.Truncated
 	if _, err := m.sessionStore.RecordCompaction(m.activeSession.SessionID, sessions.RecordCompactionInput{
 		Plan:    plan,
-		Summary: summary,
+		Summary: summaryResult.SummaryText,
 	}); err != nil {
 		return m, CompactResult{}, err
 	}
@@ -885,32 +897,47 @@ func (m model) compactActiveSession() (model, CompactResult, error) {
 		Compacted:    len(events) < len(beforeEvents)+1,
 		BeforeTokens: beforeTokens,
 		AfterTokens:  estimateTranscriptTokens(m.transcript),
-		Summary:      summary,
+		Summary:      summaryResult.SummaryText,
 	}, nil
 }
 
-func (m model) summarizeCompactionPlan(plan sessions.CompactionPlan) (string, error) {
-	if m.provider == nil {
-		return deterministicCompactionSummary(plan), nil
+func sessionEventsForRefs(events []sessions.Event, refs []sessions.EventRef) ([]sessions.Event, error) {
+	byID := make(map[string]sessions.Event, len(events))
+	for _, event := range events {
+		byID[event.ID] = event
 	}
-	stream, err := m.provider.StreamCompletion(m.ctx, zeroruntime.CompletionRequest{
-		Messages: []zeroruntime.Message{
-			{Role: zeroruntime.MessageRoleSystem, Content: "Summarize compacted Zero session events for future coding context. Preserve user goals, decisions, files, tool outcomes, blockers, and exact next steps. Omit secrets and do not invent details."},
-			{Role: zeroruntime.MessageRoleUser, Content: plan.SummaryPrompt},
-		},
+	selected := make([]sessions.Event, 0, len(refs))
+	for _, ref := range refs {
+		event, ok := byID[ref.ID]
+		if !ok || event.Sequence != ref.Sequence || event.Type != ref.Type {
+			return nil, fmt.Errorf("session changed while compaction was being planned; retry /compact")
+		}
+		selected = append(selected, event)
+	}
+	return selected, nil
+}
+
+func (m model) summarizeCompactionPlan(plan sessions.CompactionPlan, messages []zeroruntime.Message) (agent.CompactionSummaryResult, error) {
+	return agent.SummarizeCompactionMessages(messages, func(projected []zeroruntime.Message) (string, error) {
+		if m.provider == nil {
+			return deterministicCompactionSummary(plan), nil
+		}
+		stream, streamErr := m.provider.StreamCompletion(m.ctx, zeroruntime.CompletionRequest{
+			Messages: append([]zeroruntime.Message{{Role: zeroruntime.MessageRoleSystem, Content: agent.CompactionSummaryInstructions}}, projected...),
+		})
+		if streamErr != nil {
+			return "", fmt.Errorf("summarize compacted session: %w", streamErr)
+		}
+		collected := zeroruntime.CollectStream(m.ctx, stream)
+		if collected.Error != "" {
+			return "", fmt.Errorf("summarize compacted session: %s", collected.Error)
+		}
+		result := strings.TrimSpace(collected.Text)
+		if result == "" {
+			return "", fmt.Errorf("summarize compacted session: empty summary")
+		}
+		return result, nil
 	})
-	if err != nil {
-		return "", fmt.Errorf("summarize compacted session: %w", err)
-	}
-	collected := zeroruntime.CollectStream(m.ctx, stream)
-	if collected.Error != "" {
-		return "", fmt.Errorf("summarize compacted session: %s", collected.Error)
-	}
-	summary := strings.TrimSpace(collected.Text)
-	if summary == "" {
-		return "", fmt.Errorf("summarize compacted session: empty summary")
-	}
-	return summary, nil
 }
 
 func deterministicCompactionSummary(plan sessions.CompactionPlan) string {

internal/tui/session_controls_test.go

@@ -481,6 +481,15 @@ func TestCompactCommandUsesProviderSummaryWhenAvailable(t *testing.T) {
 	if err != nil {
 		t.Fatal(err)
 	}
+	for _, input := range []sessions.AppendEventInput{
+		{Type: sessions.EventToolCall, Payload: map[string]any{"id": "ask", "name": "ask_user", "arguments": `{"questions":[{"question":"Which database should remain?"}]}`}},
+		{Type: sessions.EventToolResult, Payload: map[string]any{"toolCallId": "ask", "name": "ask_user", "status": "ok", "output": "Postgres only"}},
+	} {
+		m, err = m.appendSessionEvent(input.Type, input.Payload)
+		if err != nil {
+			t.Fatal(err)
+		}
+	}
 	for _, content := range []string{
 		"old decision A",
 		"old decision B",
@@ -521,6 +530,15 @@ func TestCompactCommandUsesProviderSummaryWhenAvailable(t *testing.T) {
 	if len(provider.requests) != 1 {
 		t.Fatalf("expected one provider summarization request, got %d", len(provider.requests))
 	}
+	request := provider.requests[0]
+	if len(request.Messages) != 2 || request.Messages[0].Content != agent.CompactionSummaryInstructions {
+		t.Fatalf("manual compaction did not use the shared agent compaction prompt: %#v", request.Messages)
+	}
+	for _, want := range []string{"Which database should remain?", "Postgres only"} {
+		if !strings.Contains(request.Messages[1].Content, want) {
+			t.Fatalf("manual compaction projection lost %q: %q", want, request.Messages[1].Content)
+		}
+	}
 	if next.lastCompactResult == nil || next.lastCompactResult.Summary != "Provider summary keeps the actual old decisions." {
 		t.Fatalf("expected provider summary result, got %#v", next.lastCompactResult)
 	}
@@ -533,6 +551,56 @@ func TestCompactCommandUsesProviderSummaryWhenAvailable(t *testing.T) {
 	}
 }
 
+func TestManualCompactionPersistsStructuralTruncationMetadata(t *testing.T) {
+	store := sessions.NewStore(sessions.StoreOptions{RootDir: t.TempDir()})
+	provider := &fakeProvider{events: []zeroruntime.StreamEvent{
+		{Type: zeroruntime.StreamEventText, Content: "Bounded summary."},
+		{Type: zeroruntime.StreamEventDone},
+	}}
+	m := newModel(context.Background(), Options{ModelName: "gpt-4.1", Provider: provider, SessionStore: store})
+	var err error
+	m, err = m.ensureActiveSession("compact a large session")
+	if err != nil {
+		t.Fatal(err)
+	}
+	for index := range 20 {
+		content := strings.Repeat("contextword ", 256) + string(rune('a'+index))
+		m, err = m.appendSessionEvent(sessions.EventMessage, map[string]any{"role": "user", "content": content})
+		if err != nil {
+			t.Fatal(err)
+		}
+		m.transcript = appendTranscriptRow(m.transcript, transcriptRow{kind: rowUser, text: content})
+	}
+
+	next, result, err := m.compactActiveSession()
+	if err != nil || !result.Compacted {
+		t.Fatalf("compactActiveSession() = (%#v, %v)", result, err)
+	}
+	raw, err := store.ReadEvents(next.activeSession.SessionID)
+	if err != nil {
+		t.Fatal(err)
+	}
+	latest := raw[len(raw)-1]
+	if latest.Type != sessions.EventCompaction {
+		t.Fatalf("latest event = %s, want compaction", latest.Type)
+	}
+	payload := sessionPayload(latest)
+	if !payloadBool(payload, "truncated") {
+		t.Fatalf("compaction did not persist structural truncation: %#v", payload)
+	}
+	request := provider.requests[0]
+	wantPromptChars := len(agent.CompactionSummaryInstructions)
+	for _, message := range request.Messages[1:] {
+		wantPromptChars += len(message.Content)
+		for _, call := range message.ToolCalls {
+			wantPromptChars += len(call.Name) + len(call.Arguments)
+		}
+	}
+	if promptChars, ok := payload["promptChars"].(float64); !ok || int(promptChars) != wantPromptChars {
+		t.Fatalf("promptChars = %#v, want %d", payload["promptChars"], wantPromptChars)
+	}
+}
+
 func TestCompactCommandRecordsRequestWhenNoCompactorIsAvailable(t *testing.T) {
 	m := newModel(context.Background(), Options{})
 	m.input.SetValue("/compact")

internal/zeroruntime/types.go

@@ -93,12 +93,14 @@ type ReasoningBlock struct {
 
 // Message is a normalized conversation turn passed to providers.
 type Message struct {
-	Role       MessageRole
-	Content    string
-	ToolCalls  []ToolCall
-	ToolCallID string
-	Images     []ImageBlock     // optional; nil for text-only messages
-	Reasoning  []ReasoningBlock // optional; preserved thinking blocks to replay
+	Role         MessageRole
+	Content      string
+	ToolCalls    []ToolCall
+	ToolCallID   string
+	IsError      bool             // tool-result status; ignored for non-tool messages
+	ChangedFiles []string         // durable tool-result mutation targets; ignored by providers
+	Images       []ImageBlock     // optional; nil for text-only messages
+	Reasoning    []ReasoningBlock // optional; preserved thinking blocks to replay
 }
 
 // ToolDefinition describes a model-visible tool and its JSON-schema parameters.