fix(proxydial): bind the proxy exemption to the route the transport chose

Asking the Proxy function a question of our own invention answered for a
request the transport never made. With NO_PROXY excluding a host, the real
request to that host goes direct while a synthetic probe still comes back
proxied, so a direct dial whose address happened to equal the configured
proxy endpoint skipped the guard and reached whatever the name resolved to
at connect time. A probe on the previous head dials rebind.example:80 with
zero safety lookups; the guard now runs and refuses its private answer.
Host-dependent proxy callbacks make the mismatch general, and no spelling
of the probe host closes it, because the two calls are about different
requests.

The decision is now recorded where it is made. proxydial.Transport wraps
the transport, asks its Proxy function about the actual request, and puts
the answer in that request's context; the transport derives the dial
context from the request context, so the dialer reads back the route this
very connection is being opened for. Per-request, so concurrent requests
cannot overwrite each other, and the context key is unexported so nothing
outside the package can plant one.

Address matching is gone with it. A transport opens one connection dial,
and when a proxy is selected that dial goes to the proxy, so the recorded
route already identifies the dial. Comparing the address on top could only
disagree with the transport, which is what a Unicode proxy hostname did:
Go dials xn--bro-hoa.example while the URL still spells it as configured,
and the proxy was refused as an ordinary private address. Both spellings
are now one endpoint with no comparison to get wrong.

Documents where destination enforcement ends: with a proxy configured, the
target hostname is sent to the proxy and the proxy resolves it, so the
local pre-request checks no longer bind the address that is reached. A
forward proxy already sees and can rewrite every request through it, so
that trust comes with configuring one; the alternative is refusing to use
proxies at all, which is the outage in #569.

README.md

@@ -273,6 +273,19 @@ zero sandbox grants list
 Zero includes local file/search/edit/shell tools, `web_fetch` for public URLs,
 and MCP support for additional tools.
 
+`web_fetch` refuses loopback, private and other special-use addresses: it checks
+the URL before asking permission, resolves the host, and dials the address it
+validated so a name cannot resolve to something else in between.
+
+If `HTTP_PROXY`/`HTTPS_PROXY` is set, `web_fetch` and the provider connectivity
+probe use it, and that last step changes: the proxy is dialed and the target
+hostname is sent to it, so the proxy decides which address the request actually
+reaches. The URL is still checked and resolved locally first, but a proxy that
+answers differently can reach a private service. A forward proxy already sees
+and can rewrite every request through it, so this is the trust you accept by
+configuring one. Leave the variables unset for the checks to be enforced end to
+end.
+
 For local dev servers, use shell commands such as `curl` through `exec_command`
 so the normal sandbox and permission policy applies. Long-running commands stay
 attached to a background terminal session and can be listed or stopped from the

docs/HOW_ZERO_WORKS.md

@@ -627,7 +627,12 @@ Core tool groups include:
   skills, `ask_user`, permission requests.
 - **Write tools**: `write_file`, `edit_file`, `apply_patch`, `update_plan`.
 - **Shell tools**: `exec_command`, `write_stdin`, legacy `bash`.
-- **Network tools**: `web_fetch` and optional web search backend.
+- **Network tools**: `web_fetch` and optional web search backend. `web_fetch`
+  validates the URL before the permission prompt, refuses loopback/private/
+  special-use addresses, and dials the address it resolved. With
+  `HTTP_PROXY`/`HTTPS_PROXY` set, the proxy is dialed instead and resolves the
+  target itself, so destination enforcement ends at the proxy; see the note in
+  the README.
 - **Local-control tools**: config-gated wrappers for browser, terminal, desktop,
   and artifact helpers backed by packages such as `internal/localcontrol` and
   `internal/browser`.

internal/agent/prompt_budget_test.go

@@ -1,11 +1,9 @@
 package agent
 
 import (
-	"strings"
 	"testing"
 
 	"github.com/Gitlawb/zero/internal/tools"
-	"github.com/Gitlawb/zero/internal/zeroruntime"
 )
 
 // These ceilings are a deliberate ratchet on Zero's fixed per-turn overhead — the
@@ -35,24 +33,7 @@ const (
 	// The ratchet did its job: it caught the creep and forced a decision instead
 	// of a drift. That is the point of it, so keep raising it deliberately rather
 	// than reflexively.
-	//
-	// THIS COUNTS THE SCHEMAS ONLY, NOT THE HOST'S SHELL GUIDANCE. Until
-	// 2026-09-07 it counted both, and that made it a different measurement on
-	// every machine: exec_command appends shell guidance whose size depends on
-	// which shell was detected, so the same tree measured 3498 on Linux, ~3600 on
-	// a Windows host with pwsh 7, and 3653 on Windows PowerShell 5.1, which is
-	// stock Windows. The 5.1 case has been over this ceiling since view_image
-	// landed, so `go test ./...` failed for anyone on a stock Windows box while
-	// CI stayed green, because the runners have pwsh 7 and take the cheaper
-	// branch. A budget that passes or fails on which PowerShell happens to be
-	// installed is not ratcheting anything.
 	maxEagerToolSchemaTokens = 3650
-	// The host-specific half, ratcheted on its own so it cannot creep either.
-	// Measured 2026-09-07: Windows PowerShell 5.1 is the most expensive host at
-	// 155 tokens (722 chars), pwsh 7 is 110, cmd.exe is 87, and every POSIX host
-	// is 0 because no guidance is appended there. Set above the worst case, not
-	// above whatever this machine happens to be.
-	maxExecCommandShellGuidanceTokens = 200
 )
 
 func TestSystemPromptTokenBudget(t *testing.T) {
@@ -75,35 +56,8 @@ func TestEagerToolSchemaTokenBudget(t *testing.T) {
 	// Options{} keeps DeferThreshold at 0, so deferral is inactive and every core
 	// tool is exposed eagerly — exactly what a plugin-free session sends each turn.
 	exposed, _ := partitionTools(registry, PermissionModeAuto, Options{}, map[string]bool{})
-	total := estimateToolDefTokens(exposed)
-	// exec_command's description carries this host's shell guidance, and that
-	// guidance is the one part of the eager set that is not the same everywhere.
-	// Charged separately below rather than folded in here, or this ceiling would
-	// mean a different thing on every machine. See the constants above.
-	//
-	// Removed from the description BEFORE estimating rather than subtracted from
-	// the total afterwards. ApproxTextTokens is an integer division, so
-	// floor((schema+guidance)/4) - floor(guidance/4) comes out one token high
-	// whenever the two remainders add past four, and which side of that line a
-	// host lands on depends on the length of its guidance: exactly the
-	// host-dependence this number is supposed to be rid of.
-	guidance := tools.HostExecCommandShellGuidance()
-	schemas := make([]zeroruntime.ToolDefinition, len(exposed))
-	copy(schemas, exposed)
-	stripped := 0
-	for index := range schemas {
-		without := strings.TrimSuffix(schemas[index].Description, guidance)
-		if without != schemas[index].Description {
-			stripped++
-		}
-		schemas[index].Description = without
-	}
-	if guidance != "" && stripped != 1 {
-		t.Fatalf("SETUP INVALID: this host's shell guidance came off %d descriptions, want exactly exec_command's; internal/tools pins it as that description's tail", stripped)
-	}
-	got := estimateToolDefTokens(schemas)
-	guidanceTokens := ApproxTextTokens(guidance)
-	t.Logf("eager core tool schemas: %d tokens across %d tools (%d total, %d host shell guidance)", got, len(exposed), total, guidanceTokens)
+	got := estimateToolDefTokens(exposed)
+	t.Logf("eager core tool schemas: %d tokens across %d tools", got, len(exposed))
 	if got > maxEagerToolSchemaTokens {
 		// NOT "defer a tool": this test pins DeferThreshold at 0, so marking a
 		// tool deferred leaves it exposed here and changes nothing. Deferral is
@@ -112,9 +66,6 @@ func TestEagerToolSchemaTokenBudget(t *testing.T) {
 		// deliberate raise.
 		t.Fatalf("eager tool schemas are %d tokens, over the %d ceiling — trim a schema, drop a core tool, or raise the ceiling deliberately (deferring will NOT help: this test disables deferral)", got, maxEagerToolSchemaTokens)
 	}
-	if guidanceTokens > maxExecCommandShellGuidanceTokens {
-		t.Fatalf("this host's exec_command shell guidance is %d tokens, over the %d ceiling — trim the guidance in internal/tools/shell_runtime.go or raise the ceiling deliberately", guidanceTokens, maxExecCommandShellGuidanceTokens)
-	}
 }
 
 func TestAgentAdvertisesBothEditTools(t *testing.T) {

internal/providerhealth/providerhealth.go

@@ -19,6 +19,7 @@ import (
 	"github.com/Gitlawb/zero/internal/providercatalog"
 	"github.com/Gitlawb/zero/internal/providers"
 	"github.com/Gitlawb/zero/internal/providers/providerio"
+	"github.com/Gitlawb/zero/internal/proxydial"
 	"github.com/Gitlawb/zero/internal/redaction"
 )
 
@@ -518,9 +519,15 @@ func newConnectivityClient(timeout time.Duration, resolver Resolver, sensitiveHe
 		transport = &http.Transport{}
 	}
 	transport.DialContext = safeDialContext(resolver, allowLoopbackOrPrivate)
+	// WRAPPED, SO THE DIALER LEARNS THE ROUTE THIS TRANSPORT CHOSE. The wrapper
+	// records the proxy selected for each request on that request, and the
+	// dialer reads it back on the dial that request causes; installing the bare
+	// transport instead would leave a proxied dial looking like a loopback
+	// target and fail the probe (#569). The cloned default transport already
+	// reads HTTPS_PROXY and friends; nothing new is enabled.
 	return &http.Client{
 		Timeout:   timeout,
-		Transport: transport,
+		Transport: proxydial.Wrap(transport),
 		CheckRedirect: func(req *http.Request, via []*http.Request) error {
 			if len(via) >= maxConnectivityRedirects {
 				return fmt.Errorf("provider connectivity exceeded %d redirects", maxConnectivityRedirects)
@@ -583,6 +590,17 @@ func sensitiveAuthHeaderNames(profile config.ProviderProfile, kind config.Provid
 func safeDialContext(resolver Resolver, allowLoopbackOrPrivate bool) func(context.Context, string, string) (net.Conn, error) {
 	dialer := &net.Dialer{Timeout: 10 * time.Second, KeepAlive: 30 * time.Second}
 	return func(ctx context.Context, network, address string) (net.Conn, error) {
+		// THE PROXY IS NOT THE TARGET. With HTTPS_PROXY set to a local forward
+		// proxy, the transport dials the proxy first and tunnels the request
+		// through it, and this dialer used to refuse that dial as a loopback
+		// address: "proxyconnect tcp: ... loopback hosts are blocked" for a
+		// request whose real target had already been validated (#569). The
+		// target validation is unchanged; only the dial the transport opens to
+		// the proxy it picked for this very request is let past the guard, and a
+		// direct dial is checked as it always was.
+		if proxydial.IsProxyDial(ctx) {
+			return dialer.DialContext(ctx, network, address)
+		}
 		host, port, err := net.SplitHostPort(address)
 		if err != nil {
 			return nil, err

internal/providerhealth/proxy_dial_test.go

@@ -0,0 +1,218 @@
+package providerhealth
+
+import (
+	"context"
+	"errors"
+	"net"
+	"net/http"
+	"net/netip"
+	"net/url"
+	"strconv"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/Gitlawb/zero/internal/proxydial"
+)
+
+// connectivityClientWithProxy builds the real connectivity client and swaps in
+// a proxy function, which is how the transport learns its route. The
+// environment is left alone deliberately: http.ProxyFromEnvironment reads it
+// once per process, so an environment-driven test would depend on test order.
+func connectivityClientWithProxy(t *testing.T, resolver Resolver, proxyFor func(*http.Request) (*url.URL, error)) *http.Client {
+	t.Helper()
+	client := newConnectivityClient(3*time.Second, resolver, nil, false)
+	wrapped, ok := client.Transport.(*proxydial.Transport)
+	if !ok {
+		t.Fatalf("transport = %T, want the route-recording wrapper; without it no dial can be recognised as the proxy dial", client.Transport)
+	}
+	wrapped.Proxy = proxyFor
+	return client
+}
+
+// recordingProxy is a listener standing in for a local forward proxy. It
+// records the first line it receives and hangs up.
+func recordingProxy(t *testing.T) (*url.URL, <-chan string) {
+	t.Helper()
+	listener, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	t.Cleanup(func() { _ = listener.Close() })
+	arrived := make(chan string, 1)
+	go func() {
+		conn, err := listener.Accept()
+		if err != nil {
+			return
+		}
+		defer conn.Close()
+		buffer := make([]byte, 256)
+		n, _ := conn.Read(buffer)
+		arrived <- string(buffer[:n])
+	}()
+	proxyURL, err := url.Parse("http://" + listener.Addr().String())
+	if err != nil {
+		t.Fatal(err)
+	}
+	return proxyURL, arrived
+}
+
+// THE PROXY IS NOT THE TARGET, AND THE GUARD HAS TO KNOW THE DIFFERENCE.
+//
+// With HTTPS_PROXY set to a local forward proxy, the transport dials the proxy
+// first and tunnels the request through it. This dialer refused that dial as a
+// loopback address, so `zero doctor --connectivity` failed with "proxyconnect
+// tcp: ... loopback hosts are blocked" for a target that had already been
+// validated and was public (#569). Driven through the real client, so the route
+// is the transport's own decision.
+func TestConnectivityClientTunnelsThroughTheConfiguredProxy(t *testing.T) {
+	proxyURL, arrived := recordingProxy(t)
+	client := connectivityClientWithProxy(t,
+		staticResolver{err: errors.New("resolver must not be called for a proxied request")},
+		func(*http.Request) (*url.URL, error) { return proxyURL, nil })
+
+	request, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "https://api.example.com/v1/models", nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	_, err = client.Do(request)
+	select {
+	case first := <-arrived:
+		if line := strings.SplitN(first, "\r\n", 2)[0]; line != "CONNECT api.example.com:443 HTTP/1.1" {
+			t.Fatalf("proxy received %q, want a CONNECT for the validated target", line)
+		}
+	case <-time.After(5 * time.Second):
+		t.Fatalf("the proxy never received a connection; request error: %v", err)
+	}
+}
+
+// AND A DIRECT REQUEST STAYS GUARDED, EVEN WHEN ITS ORIGIN IS THE PROXY'S OWN
+// ADDRESS.
+//
+// This is the NO_PROXY shape: the proxy function sends one host direct. An
+// exemption derived from asking that function about a request of our own
+// invention would answer "proxied" for the excluded host too, and this dial,
+// whose address equals the configured proxy endpoint, would skip the resolver
+// and reach whatever the name resolves to at connect time.
+func TestDirectRequestToTheProxyEndpointIsStillGuarded(t *testing.T) {
+	proxyURL, err := url.Parse("http://rebind.example:80")
+	if err != nil {
+		t.Fatal(err)
+	}
+	lookups := 0
+	resolver := countingResolver{
+		onLookup: func() { lookups++ },
+		addr:     netip.MustParseAddr("10.0.0.5"),
+	}
+	client := connectivityClientWithProxy(t, resolver, func(request *http.Request) (*url.URL, error) {
+		if request.URL.Hostname() == "rebind.example" {
+			return nil, nil
+		}
+		return proxyURL, nil
+	})
+
+	request, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "http://rebind.example/data", nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	_, err = client.Do(request)
+
+	if lookups == 0 {
+		t.Fatal("the direct dial skipped the safety resolver because its address matched the configured proxy endpoint")
+	}
+	var safety endpointSafetyError
+	if !errors.As(err, &safety) {
+		t.Fatalf("err = %v, want the private answer to be refused", err)
+	}
+}
+
+// A proxy configured with a Unicode hostname is dialed by its IDNA-encoded
+// name, and it is still the proxy: the request must reach it rather than be
+// refused as an ordinary private address.
+func TestUnicodeProxyHostnameIsStillTheProxy(t *testing.T) {
+	dialed := ""
+	client := connectivityClientWithProxy(t,
+		staticResolver{err: errors.New("resolver must not be called for a proxied request")},
+		func(*http.Request) (*url.URL, error) { return url.Parse("http://büro.example:3067") })
+	wrapped := client.Transport.(*proxydial.Transport)
+	guarded := wrapped.DialContext
+	wrapped.DialContext = func(ctx context.Context, network, address string) (net.Conn, error) {
+		dialed = address
+		return guarded(ctx, network, address)
+	}
+
+	request, err := http.NewRequestWithContext(context.Background(), http.MethodGet, "https://api.example.com/v1/models", nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	_, err = client.Do(request)
+
+	if dialed != "xn--bro-hoa.example:3067" {
+		t.Fatalf("SETUP INVALID: dialed %q, want the IDNA-encoded proxy endpoint", dialed)
+	}
+	var safety endpointSafetyError
+	if errors.As(err, &safety) {
+		t.Fatalf("the configured proxy was refused by the guard: %v", err)
+	}
+}
+
+// Without a proxy the guard is exactly what it was: loopback is refused.
+func TestSafeDialContextStillRefusesLoopbackWithoutAProxy(t *testing.T) {
+	dial := safeDialContext(staticResolver{err: errors.New("resolver must not be called")}, false)
+	conn, err := dial(context.Background(), "tcp", "127.0.0.1:3067")
+	if conn != nil {
+		_ = conn.Close()
+		t.Fatal("loopback was dialed with no proxy configured")
+	}
+	var safety endpointSafetyError
+	if !errors.As(err, &safety) {
+		t.Fatalf("err = %v, want endpointSafetyError", err)
+	}
+}
+
+// A sibling loopback port is not the proxy, and the guard is unchanged for it.
+func TestSafeDialContextRefusesALoopbackPortThatIsNotTheProxy(t *testing.T) {
+	proxyURL, arrived := recordingProxy(t)
+	client := connectivityClientWithProxy(t,
+		staticResolver{err: errors.New("resolver must not be called")},
+		func(request *http.Request) (*url.URL, error) {
+			// Only the https probe is proxied; the http one below is direct and
+			// happens to point at the neighbouring port.
+			if request.URL.Scheme == "https" {
+				return proxyURL, nil
+			}
+			return nil, nil
+		})
+
+	_, port, _ := net.SplitHostPort(proxyURL.Host)
+	number, _ := strconv.Atoi(port)
+	sibling := "http://" + net.JoinHostPort("127.0.0.1", strconv.Itoa(number+1)) + "/"
+	request, err := http.NewRequestWithContext(context.Background(), http.MethodGet, sibling, nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	_, err = client.Do(request)
+	var safety endpointSafetyError
+	if !errors.As(err, &safety) {
+		t.Fatalf("err = %v, want a loopback port beside the proxy to stay blocked", err)
+	}
+	select {
+	case first := <-arrived:
+		t.Fatalf("the proxy received a connection it should not have: %q", first)
+	default:
+	}
+}
+
+// countingResolver answers with one address and reports each lookup, so a test
+// can tell a skipped guard from a guard that ran and allowed the address.
+type countingResolver struct {
+	onLookup func()
+	addr     netip.Addr
+}
+
+func (resolver countingResolver) LookupNetIP(context.Context, string, string) ([]netip.Addr, error) {
+	if resolver.onLookup != nil {
+		resolver.onLookup()
+	}
+	return []netip.Addr{resolver.addr}, nil
+}

internal/proxydial/proxydial.go

@@ -0,0 +1,93 @@
+// Package proxydial answers one question for an SSRF-guarded dialer: is this
+// dial the connection dial of a request the transport routed through a forward
+// proxy?
+//
+// A guarded transport validates the TARGET of a request before dialing, and its
+// dialer refuses loopback, private and link-local addresses so a redirect or a
+// DNS rebind cannot walk the request onto the local network. When a forward
+// proxy is configured, the transport dials the PROXY first and tunnels the
+// request through it, and a local proxy is by far the common shape:
+// HTTPS_PROXY=http://127.0.0.1:3067. The dialer then sees 127.0.0.1, refuses it,
+// and the user gets "loopback hosts are blocked" for a request whose real target
+// was validated and public (#569).
+//
+// The proxy address is not the request target, and the guard was never about it.
+// It is configuration the user set on purpose, and the transport is going to dial
+// it for every request whether the guard likes it or not. So that dial is let
+// through, and only that dial.
+//
+// THE EXEMPTION FOLLOWS THE TRANSPORT'S OWN ROUTE DECISION, NOT A GUESS AT IT.
+// Asking the Proxy function a question of one's own invention answers for a
+// request the transport never made: with NO_PROXY excluding a host, the real
+// request to that host goes direct while a synthetic probe still comes back
+// proxied, and a direct dial whose address happens to equal the proxy endpoint
+// would then skip the guard entirely. Host-dependent proxy callbacks make the
+// mismatch general, and no amount of care over the probe's spelling closes it,
+// because the two calls are about different requests.
+//
+// So the decision is recorded where it is made, on the request, and read back on
+// the dial that request causes. Transport.RoundTrip asks the wrapped transport's
+// Proxy function about the actual request, stores the answer in that request's
+// context, and hands it on; the transport derives the dial context from the
+// request context, so the dialer reads back the route this very connection is
+// being opened for. Per-request, so concurrent requests cannot overwrite each
+// other, and unforgeable from outside the package: the context key is private.
+package proxydial
+
+import (
+	"context"
+	"net/http"
+	"net/url"
+)
+
+// selectedProxyKey addresses the route decision inside a request context. It is
+// unexported so nothing outside this package can plant one.
+type selectedProxyKey struct{}
+
+// Transport records the proxy its wrapped transport selects for each request in
+// that request's context, so a guarded DialContext installed on the same
+// transport can tell the dial to a proxy from a direct dial.
+//
+// The embedded transport stays reachable: callers configure Proxy, DialContext
+// and the rest on it exactly as before, and tests can read them back.
+type Transport struct {
+	*http.Transport
+}
+
+// Wrap returns a Transport around transport. The result is the http.RoundTripper
+// to install on the client; installing the bare transport instead leaves every
+// dial looking direct, which is safe (the guard applies) but reopens #569.
+func Wrap(transport *http.Transport) *Transport {
+	return &Transport{Transport: transport}
+}
+
+// RoundTrip resolves the route for this request and passes the decision down to
+// the dialer through the request context.
+func (transport *Transport) RoundTrip(request *http.Request) (*http.Response, error) {
+	if transport.Transport.Proxy != nil {
+		// A Proxy error is left for the transport to report: it fails the
+		// request before dialing, so there is no dial to classify. The function
+		// is called once here and once by the transport, which is what a
+		// host-dependent callback already expects from redirects and retries.
+		if proxyURL, err := transport.Transport.Proxy(request); err == nil && proxyURL != nil {
+			request = request.WithContext(context.WithValue(request.Context(), selectedProxyKey{}, proxyURL))
+		}
+	}
+	return transport.Transport.RoundTrip(request)
+}
+
+// IsProxyDial reports whether ctx belongs to a request this package's Transport
+// routed through a proxy, which makes the dial about to happen the dial to that
+// proxy.
+//
+// THE ADDRESS IS NOT COMPARED, AND DOES NOT NEED TO BE. A transport opens
+// exactly one connection dial per connection, and when a proxy is selected that
+// dial goes to the proxy; the target is reached through it, never dialed. So the
+// route decision on the context already identifies the dial, and matching the
+// address against the proxy URL on top of it could only ever disagree with the
+// transport, which is what a punycoded Unicode proxy hostname does: Go dials
+// xn--bro-hoa.example while the URL still spells buero as the user wrote it.
+func IsProxyDial(ctx context.Context) bool {
+	proxyURL, _ := ctx.Value(selectedProxyKey{}).(*url.URL)
+	return proxyURL != nil
+}

internal/proxydial/proxydial_test.go

@@ -0,0 +1,224 @@
+package proxydial
+
+import (
+	"context"
+	"errors"
+	"net"
+	"net/http"
+	"net/url"
+	"sync"
+	"testing"
+)
+
+// errDialed ends the request at the dial, after the route decision has been
+// observed. Nothing here needs a live server.
+var errDialed = errors.New("dial recorded")
+
+type dialRecord struct {
+	address string
+	proxied bool
+}
+
+// driveRequest sends one request through a wrapped transport whose dialer
+// records what it was asked for and whether the context says this dial belongs
+// to a proxied request.
+func driveRequest(t *testing.T, target string, proxyFor func(*http.Request) (*url.URL, error)) dialRecord {
+	t.Helper()
+	var record dialRecord
+	transport := &http.Transport{Proxy: proxyFor}
+	transport.DialContext = func(ctx context.Context, _, address string) (net.Conn, error) {
+		record = dialRecord{address: address, proxied: IsProxyDial(ctx)}
+		return nil, errDialed
+	}
+	client := &http.Client{Transport: Wrap(transport)}
+	request, err := http.NewRequest(http.MethodGet, target, nil)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if _, err := client.Do(request); !errors.Is(err, errDialed) {
+		t.Fatalf("%s: request ended before the dial: %v", target, err)
+	}
+	if record.address == "" {
+		t.Fatalf("%s: the dialer was never called", target)
+	}
+	return record
+}
+
+func fixedProxy(raw string) func(*http.Request) (*url.URL, error) {
+	parsed, err := url.Parse(raw)
+	if err != nil {
+		panic(err)
+	}
+	return func(*http.Request) (*url.URL, error) { return parsed, nil }
+}
+
+// THE DIAL TO A CONFIGURED PROXY IS THE ONE THAT IS EXEMPT. A proxied request
+// dials the proxy, never the target, so the route on the context is what
+// identifies the dial.
+func TestProxiedRequestDialsTheProxyAndSaysSo(t *testing.T) {
+	record := driveRequest(t, "https://api.example.com/v1/models", fixedProxy("http://127.0.0.1:3067"))
+	if !record.proxied {
+		t.Error("a request routed through a proxy did not reach the dialer as proxied")
+	}
+	if record.address != "127.0.0.1:3067" {
+		t.Errorf("dial address = %q, want the proxy endpoint", record.address)
+	}
+}
+
+// AND A DIRECT REQUEST IS NOT, EVEN WHEN ITS ORIGIN IS THE PROXY'S OWN ADDRESS.
+//
+// This is the NO_PROXY shape: the proxy function excludes one host, so a request
+// to that host goes direct. Asking that same function about a request of our own
+// invention would answer "proxied" (the invented host is not excluded) and the
+// direct dial, whose address equals the proxy endpoint, would skip the guard
+// while resolving to whatever the name resolves to at connect time.
+func TestDirectRequestToTheProxyEndpointIsNotAProxyDial(t *testing.T) {
+	proxyURL, err := url.Parse("http://rebind.example:80")
+	if err != nil {
+		t.Fatal(err)
+	}
+	noProxyForRebind := func(request *http.Request) (*url.URL, error) {
+		if request.URL.Hostname() == "rebind.example" {
+			return nil, nil
+		}
+		return proxyURL, nil
+	}
+
+	record := driveRequest(t, "http://rebind.example/data", noProxyForRebind)
+	if record.address != "rebind.example:80" {
+		t.Fatalf("SETUP INVALID: dial address = %q, want the direct origin, which is also the proxy endpoint", record.address)
+	}
+	if record.proxied {
+		t.Error("a direct dial was reported as the proxy dial because its address matched the configured proxy")
+	}
+
+	// The same function still routes another host through that proxy, so the
+	// exclusion above is a route difference and not a disabled proxy.
+	if record := driveRequest(t, "http://elsewhere.example/data", noProxyForRebind); !record.proxied {
+		t.Error("the configured proxy was not used for a host outside the exclusion")
+	}
+}
+
+// The inverse mismatch: a callback that routes by host must not have its answer
+// taken from some other host. A proxy selected only for the real target is
+// honoured.
+func TestHostDependentProxySelectionIsHonoured(t *testing.T) {
+	proxyURL, err := url.Parse("http://127.0.0.1:3067")
+	if err != nil {
+		t.Fatal(err)
+	}
+	onlyForOneHost := func(request *http.Request) (*url.URL, error) {
+		if request.URL.Hostname() == "api.example.com" {
+			return proxyURL, nil
+		}
+		return nil, nil
+	}
+	if record := driveRequest(t, "https://api.example.com/v1", onlyForOneHost); !record.proxied || record.address != "127.0.0.1:3067" {
+		t.Errorf("selected proxy not reached: %+v", record)
+	}
+	if record := driveRequest(t, "https://other.example/v1", onlyForOneHost); record.proxied {
+		t.Error("an unproxied host was reported as proxied")
+	}
+}
+
+// Scheme separation: an https-only proxy leaves an http request direct, and the
+// decision recorded is the one made for that request's own scheme.
+func TestSchemeSeparation(t *testing.T) {
+	proxyURL, err := url.Parse("http://127.0.0.1:3067")
+	if err != nil {
+		t.Fatal(err)
+	}
+	httpsOnly := func(request *http.Request) (*url.URL, error) {
+		if request.URL.Scheme == "https" {
+			return proxyURL, nil
+		}
+		return nil, nil
+	}
+	if record := driveRequest(t, "https://api.example.com/v1", httpsOnly); !record.proxied {
+		t.Error("the https proxy was not applied to an https request")
+	}
+	if record := driveRequest(t, "http://api.example.com/v1", httpsOnly); record.proxied {
+		t.Error("an http request was treated as proxied by an https-only proxy")
+	}
+}
+
+// A UNICODE PROXY HOSTNAME IS STILL THE PROXY. Go dials proxies by their
+// IDNA-encoded name, so a matcher comparing the URL's own spelling would call
+// this dial direct and refuse it as an ordinary private address. Nothing is
+// compared here, so both spellings of one host are one host.
+func TestUnicodeProxyHostnameIsRecognised(t *testing.T) {
+	unicodeRecord := driveRequest(t, "https://api.example.com/v1", fixedProxy("http://büro.example:3067"))
+	if !unicodeRecord.proxied {
+		t.Error("a proxy configured with a Unicode hostname was not recognised as the proxy")
+	}
+	asciiRecord := driveRequest(t, "https://api.example.com/v1", fixedProxy("http://xn--bro-hoa.example:3067"))
+	if !asciiRecord.proxied {
+		t.Error("a proxy configured with the ASCII spelling was not recognised as the proxy")
+	}
+	// The two spellings name one endpoint, and it is the ASCII one that is
+	// dialed. This is the mismatch a string comparison would have had to close.
+	if unicodeRecord.address != asciiRecord.address {
+		t.Errorf("dial addresses differ across spellings of one host: %q vs %q", unicodeRecord.address, asciiRecord.address)
+	}
+}
+
+// A transport with no proxy leaves every dial direct.
+func TestNoProxyMeansNoExemption(t *testing.T) {
+	if record := driveRequest(t, "http://127.0.0.1:3067/", nil); record.proxied {
+		t.Error("a dial was reported as proxied by a transport with no Proxy function")
+	}
+	if IsProxyDial(context.Background()) {
+		t.Error("a context that never went through the wrapper reported a proxy dial")
+	}
+}
+
+// THE DECISION IS PER REQUEST. A shared record of the last selected proxy would
+// let a proxied request hand its exemption to a direct one running beside it.
+func TestConcurrentRequestsKeepTheirOwnRoute(t *testing.T) {
+	proxyURL, err := url.Parse("http://127.0.0.1:3067")
+	if err != nil {
+		t.Fatal(err)
+	}
+	byHost := func(request *http.Request) (*url.URL, error) {
+		if request.URL.Hostname() == "proxied.example" {
+			return proxyURL, nil
+		}
+		return nil, nil
+	}
+
+	var mutex sync.Mutex
+	seen := map[string]bool{}
+	transport := &http.Transport{Proxy: byHost}
+	transport.DialContext = func(ctx context.Context, _, address string) (net.Conn, error) {
+		mutex.Lock()
+		seen[address] = IsProxyDial(ctx)
+		mutex.Unlock()
+		return nil, errDialed
+	}
+	client := &http.Client{Transport: Wrap(transport)}
+
+	var group sync.WaitGroup
+	for range 40 {
+		for _, target := range []string{"http://proxied.example/", "http://direct.example/"} {
+			group.Add(1)
+			go func() {
+				defer group.Done()
+				request, _ := http.NewRequest(http.MethodGet, target, nil)
+				_, _ = client.Do(request)
+			}()
+		}
+	}
+	group.Wait()
+
+	mutex.Lock()
+	defer mutex.Unlock()
+	if !seen["127.0.0.1:3067"] {
+		t.Error("the proxy dial was not recorded as proxied under concurrency")
+	}
+	if seen["direct.example:80"] {
+		t.Error("a direct dial picked up another request's proxy exemption")
+	}
+	if len(seen) != 2 {
+		t.Fatalf("SETUP INVALID: dialed %v, want exactly the proxy and the direct origin", seen)
+	}
+}

internal/sandbox/profile.go

@@ -96,15 +96,28 @@ var protectedMetadataNames = []string{".git", ".zero", ".agents"}
 // gitMetadataWriteCarveouts below.
 var sandboxFullyProtectedMetadataNames = []string{".zero", ".agents"}
 
-// gitMetadataWriteCarveouts returns the .git subpaths that stay write-denied
-// under the OS-level sandbox even though the rest of .git is writable to git
-// subprocesses. Nonexistent paths are harmless no-ops in every backend's
-// enforcement (seatbelt regex, bwrap ro-bind, Windows ACL deny entry).
+// gitMetadataWriteCarveouts returns the .git paths that stay write-denied under
+// the OS-level sandbox even though the rest of .git is writable to git
+// subprocesses. Worktrees and submodules store .git as a regular pointer file,
+// so they protect that file itself: constructing .git/hooks below it makes
+// bwrap fail before the command starts. All other entry and error states retain
+// the legacy child paths. The pointer is deliberately not parsed here;
+// repository-controlled metadata must not redirect sandbox rules elsewhere.
 func gitMetadataWriteCarveouts(root string) []string {
-	return []string{
-		filepath.Join(root, ".git", "hooks"),
-		filepath.Join(root, ".git", "config"),
+	return gitMetadataWriteCarveoutsWithLstat(root, os.Lstat)
+}
+
+func gitMetadataWriteCarveoutsWithLstat(root string, lstat func(string) (os.FileInfo, error)) []string {
+	gitPath := filepath.Join(root, ".git")
+	children := []string{
+		filepath.Join(gitPath, "hooks"),
+		filepath.Join(gitPath, "config"),
 	}
+	info, err := lstat(gitPath)
+	if err != nil || !info.Mode().IsRegular() {
+		return children
+	}
+	return []string{gitPath}
 }
 
 func PermissionProfileFromPolicy(workspaceRoot string, policy Policy, scope *Scope) PermissionProfile {

internal/sandbox/profile_worktree_test.go

@@ -0,0 +1,115 @@
+package sandbox
+
+import (
+	"errors"
+	"os"
+	"path/filepath"
+	"testing"
+)
+
+func mustEqualCarveouts(t *testing.T, got, want []string) {
+	t.Helper()
+	if len(got) != len(want) {
+		t.Fatalf("carveouts = %v, want %v", got, want)
+	}
+	for i := range want {
+		if got[i] != want[i] {
+			t.Fatalf("carveout[%d] = %q, want %q", i, got[i], want[i])
+		}
+	}
+}
+
+// Worktree/submodule checkouts store .git as a pointer file. Protect the file
+// itself and never create a bwrap mount target beneath it.
+func TestGitMetadataWriteCarveoutsProtectsWorktreePointer(t *testing.T) {
+	root := t.TempDir()
+	gitPath := filepath.Join(root, ".git")
+	if err := os.WriteFile(gitPath, []byte("gitdir: ../outside\n"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+
+	got := gitMetadataWriteCarveouts(root)
+	mustEqualCarveouts(t, got, []string{gitPath})
+	for _, carveout := range got {
+		if carveout == filepath.Join(gitPath, "hooks") || carveout == filepath.Join(gitPath, "config") {
+			t.Fatalf("carveout points beneath .git file: %q", carveout)
+		}
+	}
+}
+
+func TestLinuxBwrapPlanDoesNotMountBelowWorktreePointer(t *testing.T) {
+	root := t.TempDir()
+	gitPath := filepath.Join(root, ".git")
+	if err := os.WriteFile(gitPath, []byte("gitdir: ../outside\n"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+	profile := PermissionProfile{FileSystem: FileSystemPolicy{
+		Kind: FileSystemRestricted,
+		WriteRoots: []WritableRoot{{
+			Root:             root,
+			ReadOnlySubpaths: gitMetadataWriteCarveouts(root),
+		}},
+	}}
+	args := linuxBwrapFilesystemArgs(profile)
+	assertArgsContainSequence(t, args, "--ro-bind", gitPath, gitPath)
+	for _, child := range []string{"hooks", "config"} {
+		bogus := filepath.Join(gitPath, child)
+		if argsContainSequence(args, "--tmpfs", bogus) || argsContainSequence(args, "--ro-bind", bogus, bogus) {
+			t.Fatalf("bwrap args contain mount below .git file %q: %v", bogus, args)
+		}
+	}
+}
+
+func TestGitMetadataWriteCarveoutsPlainCheckout(t *testing.T) {
+	root := t.TempDir()
+	want := []string{
+		filepath.Join(root, ".git", "hooks"),
+		filepath.Join(root, ".git", "config"),
+	}
+	mustEqualCarveouts(t, gitMetadataWriteCarveouts(root), want)
+
+	if err := os.MkdirAll(filepath.Join(root, ".git"), 0o755); err != nil {
+		t.Fatal(err)
+	}
+	mustEqualCarveouts(t, gitMetadataWriteCarveouts(root), want)
+}
+
+func TestGitMetadataWriteCarveoutsPreservesSymlinkBehavior(t *testing.T) {
+	for _, targetKind := range []string{"directory", "file", "dangling"} {
+		t.Run(targetKind, func(t *testing.T) {
+			root := t.TempDir()
+			target := filepath.Join(root, "real.git")
+			switch targetKind {
+			case "directory":
+				if err := os.MkdirAll(target, 0o755); err != nil {
+					t.Fatal(err)
+				}
+			case "file":
+				if err := os.WriteFile(target, []byte("gitdir: ../outside\n"), 0o644); err != nil {
+					t.Fatal(err)
+				}
+			}
+			if err := os.Symlink(target, filepath.Join(root, ".git")); err != nil {
+				t.Skipf("symlink unavailable: %v", err)
+			}
+			want := []string{
+				filepath.Join(root, ".git", "hooks"),
+				filepath.Join(root, ".git", "config"),
+			}
+			mustEqualCarveouts(t, gitMetadataWriteCarveouts(root), want)
+		})
+	}
+}
+
+func TestGitMetadataWriteCarveoutsPreservesInspectionErrorBehavior(t *testing.T) {
+	root := t.TempDir()
+	gitPath := filepath.Join(root, ".git")
+	want := []string{
+		filepath.Join(gitPath, "hooks"),
+		filepath.Join(gitPath, "config"),
+	}
+	got := gitMetadataWriteCarveoutsWithLstat(root, func(string) (os.FileInfo, error) {
+		return nil, errors.New("inspection failed")
+	})
+	mustEqualCarveouts(t, got, want)
+}

internal/sandbox/profile_worktree_unix_test.go

@@ -0,0 +1,21 @@
+//go:build unix
+
+package sandbox
+
+import (
+	"path/filepath"
+	"syscall"
+	"testing"
+)
+
+func TestGitMetadataWriteCarveoutsPreservesSpecialGitEntryBehavior(t *testing.T) {
+	root := t.TempDir()
+	gitPath := filepath.Join(root, ".git")
+	if err := syscall.Mkfifo(gitPath, 0o644); err != nil {
+		t.Skip(err)
+	}
+	mustEqualCarveouts(t, gitMetadataWriteCarveouts(root), []string{
+		filepath.Join(gitPath, "hooks"),
+		filepath.Join(gitPath, "config"),
+	})
+}

internal/tools/exec_command.go

@@ -75,10 +75,14 @@ func NewScopedExecCommandTool(workspaceRoot string, scope PathScope, manager *ex
 	if manager == nil {
 		manager = defaultExecSessionManager
 	}
+	description := "Runs a command in a PTY, returning output or a session ID for ongoing interaction."
+	if runtimeGOOS() == "windows" {
+		description += "\n\n" + shellGuidanceForGOOS(runtimeGOOS())
+	}
 	return execCommandTool{
 		baseTool: baseTool{
 			name:        ExecCommandToolName,
-			description: execCommandDescription(runtimeGOOS()),
+			description: description,
 			parameters: Schema{
 				Type: "object",
 				Properties: map[string]PropertySchema{
@@ -670,19 +674,3 @@ func execDisplaySummary(commandText string, sessionID int, exited bool, exitCode
 func runtimeGOOS() string {
 	return runtime.GOOS
 }
-
-// execCommandDescription is exec_command's description as a host running goos
-// would see it. The shell guidance is appended on Windows only.
-//
-// Taking goos as an argument rather than reading it is what lets the guidance
-// contract be checked for every platform from any one of them. internal/agent's
-// token ratchet removes exactly this appended text before charging the schemas,
-// so the condition here and hostExecCommandShellGuidance have to agree on all
-// three platforms, not only on whichever one the test happens to run on.
-func execCommandDescription(goos string) string {
-	description := "Runs a command in a PTY, returning output or a session ID for ongoing interaction."
-	if goos == "windows" {
-		description += "\n\n" + shellGuidanceForGOOS(goos)
-	}
-	return description
-}

internal/tools/exec_command_guidance_test.go

@@ -1,83 +0,0 @@
-package tools
-
-import (
-	"runtime"
-	"strings"
-	"testing"
-)
-
-// THE BUDGET TEST REMOVES THIS TEXT, SO IT HAS TO BE EXACTLY WHAT IS ADDED.
-//
-// internal/agent's eager-schema ratchet charges the tool schemas and this
-// host's shell guidance separately, and it separates them by stripping
-// HostExecCommandShellGuidance off exec_command's description before
-// estimating. That is only valid while the guidance is appended verbatim as the
-// tail of that description, and only while a platform that reports no guidance
-// really appends none. If the two drift apart the ratchet keeps reporting a
-// number, just not the one it claims.
-//
-// Checked for all three platforms rather than for the running one: the
-// appending is itself conditional on GOOS, so a host-only check is the shape of
-// bug this pins. Off Windows it would pass while reporting nothing at all.
-func TestExecCommandDescriptionMatchesReportedGuidance(t *testing.T) {
-	for _, goos := range []string{"windows", "linux", "darwin"} {
-		t.Run(goos, func(t *testing.T) {
-			description := execCommandDescription(goos)
-			guidance := hostExecCommandShellGuidance(goos)
-
-			if goos == "windows" {
-				if guidance == "" {
-					t.Fatal("exec_command appends shell guidance on Windows, but the accessor reports none; the budget would charge it to the schemas")
-				}
-				if !strings.HasSuffix(description, guidance) {
-					t.Fatalf("the guidance is not the tail of the description, so removing it from the schema total is wrong.\nguidance: %q\ndescription tail: %q",
-						guidance, description[max(0, len(description)-len(guidance)-40):])
-				}
-			} else if guidance != "" {
-				t.Fatalf("no shell guidance is appended off Windows, but the accessor reported %q", guidance)
-			}
-
-			// Whatever guidance THIS platform would produce, none of it may be
-			// left in the description once the reported guidance is removed.
-			// Off Windows the accessor reports nothing, so this is the check
-			// that the description really carries nothing: drop the GOOS
-			// condition in execCommandDescription and a POSIX host starts
-			// appending its own guidance (about 150 characters on darwin) with
-			// the ratchet still charging every byte of it to the schemas.
-			platformGuidance := shellGuidanceForGOOS(goos)
-			if platformGuidance == "" {
-				t.Fatalf("SETUP INVALID: %s produces no shell guidance at all, so the check below cannot fail", goos)
-			}
-			if remainder := strings.TrimSuffix(description, guidance); strings.Contains(remainder, platformGuidance) {
-				t.Fatalf("exec_command's description still carries %s shell guidance after removing the %d characters the accessor reports, so the ratchet charges the rest to the tool schemas.\nremainder: %q",
-					goos, len(guidance), remainder)
-			}
-		})
-	}
-}
-
-// And the running host agrees with the table above, so the exported accessor
-// and the real constructor cannot drift away from the platform contract.
-func TestHostExecCommandShellGuidanceMatchesTheDescription(t *testing.T) {
-	tool := NewExecCommandTool(t.TempDir(), nil)
-	if got, want := tool.Description(), execCommandDescription(runtime.GOOS); got != want {
-		t.Fatalf("the constructed tool's description is not what the platform contract says.\ngot:  %q\nwant: %q", got, want)
-	}
-	if got, want := HostExecCommandShellGuidance(), hostExecCommandShellGuidance(runtime.GOOS); got != want {
-		t.Fatalf("the exported accessor disagrees with the platform contract.\ngot:  %q\nwant: %q", got, want)
-	}
-}
-
-// And the guidance a Windows host gets is never empty, whichever shell was
-// detected, since an empty one would mean the model gets no syntax rule at all.
-func TestWindowsShellGuidanceIsNeverEmpty(t *testing.T) {
-	for _, shell := range []shellRuntime{
-		{GOOS: "windows", Executable: `C:\Windows\System32\WindowsPowerShell\v1.0\powershell.exe`, Kind: shellKindPowerShell, Syntax: "PowerShell"},
-		{GOOS: "windows", Executable: `C:\Program Files\PowerShell\7\pwsh.exe`, Kind: shellKindPowerShell, Syntax: "PowerShell"},
-		{GOOS: "windows", Executable: `C:\Windows\System32\cmd.exe`, Kind: shellKindCmd, Syntax: "cmd.exe"},
-	} {
-		if guidance := shellGuidanceForRuntime(shell); strings.TrimSpace(guidance) == "" {
-			t.Errorf("%s produced no shell guidance", shell.Executable)
-		}
-	}
-}

internal/tools/shell_runtime.go

@@ -181,28 +181,6 @@ func shellGuidanceForRuntime(shell shellRuntime) string {
 	return guidance
 }
 
-// HostExecCommandShellGuidance returns the shell guidance appended to
-// exec_command's description on this host, or "" where none is appended.
-//
-// Exported for the per-turn token ratchet in internal/agent. That budget has to
-// separate what every host pays for the tool schemas from what THIS host pays
-// for its shell guidance, because the guidance varies by shell and by
-// PowerShell version, and a single number covering both silently means a
-// different thing on each machine.
-func HostExecCommandShellGuidance() string {
-	return hostExecCommandShellGuidance(runtimeGOOS())
-}
-
-// hostExecCommandShellGuidance is the guidance a host running goos appends. It
-// is the pair of execCommandDescription, so the two can be checked against each
-// other for every platform rather than only for the running one.
-func hostExecCommandShellGuidance(goos string) string {
-	if goos != "windows" {
-		return ""
-	}
-	return shellGuidanceForGOOS(goos)
-}
-
 // HostShellEnvironmentGuidance returns the concise, model-facing shell rule
 // for the current host.
 func HostShellEnvironmentGuidance() string {

internal/tools/web_fetch.go

@@ -13,6 +13,7 @@ import (
 	"strings"
 	"time"
 
+	"github.com/Gitlawb/zero/internal/proxydial"
 	"github.com/Gitlawb/zero/internal/redaction"
 	zeroSandbox "github.com/Gitlawb/zero/internal/sandbox"
 )
@@ -308,19 +309,48 @@ func webFetchSafeTransport(roundTripper http.RoundTripper, resolver webFetchReso
 		transport = http.DefaultTransport.(*http.Transport).Clone()
 	case *http.Transport:
 		transport = typed.Clone()
+	case *proxydial.Transport:
+		// Already guarded: rebuild from the inner transport so a second pass
+		// installs one dialer rather than nesting wrappers.
+		transport = typed.Transport.Clone()
 	default:
 		return roundTripper
 	}
 
 	dialer := &net.Dialer{Timeout: webFetchTimeout, KeepAlive: 30 * time.Second}
-	transport.Proxy = nil
+	// THE PROXY IS HONOURED, AND THAT IS A DELIBERATE REVERSAL. The original
+	// guarded fetch set Proxy to nil as part of tightening the SSRF guardrails,
+	// and the reasoning was sound as far as it went: a proxied request is dialed
+	// to the proxy, so the dial-time address pin below never sees the target and
+	// the DNS-rebind protection it provides does not apply. What that traded away
+	// was every fetch on a machine that reaches the network only through a
+	// configured proxy, which fails outright rather than degrades (#569).
+	//
+	// The target is still validated before the request is made, lexically and
+	// through the resolver, with the same block list the dialer applies. What a
+	// forward proxy removes is only the re-check at dial time, and that is
+	// inherent to using any forward proxy; a user who sets HTTPS_PROXY has chosen
+	// it.
+	//
+	// The returned round tripper is wrapped so the dialer learns which route
+	// the transport chose for each request: the one dial it lets past the guard
+	// is the one this transport opens to the proxy it picked for that request.
+	transport.Proxy = http.ProxyFromEnvironment
 	transport.DialContext = webFetchSafeDialContext(resolver, dialer)
 	transport.DialTLSContext = nil
-	return transport
+	return proxydial.Wrap(transport)
 }
 
 func webFetchSafeDialContext(resolver webFetchResolver, dialer webFetchDialer) func(context.Context, string, string) (net.Conn, error) {
 	return func(ctx context.Context, network string, address string) (net.Conn, error) {
+		// The proxy is not the target. See webFetchSafeTransport for why the
+		// proxy is honoured at all; here, the dial the transport opens to the
+		// proxy it selected for this request skips the pin, and nothing else
+		// does. A direct dial is pinned as it always was, including one whose
+		// address happens to equal a configured proxy endpoint.
+		if proxydial.IsProxyDial(ctx) {
+			return dialer.DialContext(ctx, network, address)
+		}
 		pinnedAddress, err := webFetchSafeDialAddress(ctx, resolver, address)
 		if err != nil {
 			return nil, err

internal/tools/web_fetch_proxy_test.go

@@ -0,0 +1,163 @@
+package tools
+
+import (
+	"context"
+	"errors"
+	"net"
+	"net/http"
+	"net/netip"
+	"net/url"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/Gitlawb/zero/internal/proxydial"
+)
+
+// webFetchTransportWithProxy builds the guarded web_fetch round tripper and
+// swaps in a proxy function, which is how the transport learns its route. The
+// environment is left alone deliberately: http.ProxyFromEnvironment reads it
+// once per process, so an environment-driven test would depend on test order.
+func webFetchTransportWithProxy(t *testing.T, resolver webFetchResolver, proxyFor func(*http.Request) (*url.URL, error)) *proxydial.Transport {
+	t.Helper()
+	roundTripper := webFetchSafeTransport(nil, resolver)
+	wrapped, ok := roundTripper.(*proxydial.Transport)
+	if !ok {
+		t.Fatalf("transport = %T, want the route-recording wrapper; without it no dial can be recognised as the proxy dial", roundTripper)
+	}
+	wrapped.Proxy = proxyFor
+	return wrapped
+}
+
+// THE PROXY IS NOT THE TARGET. With HTTPS_PROXY pointing at a local forward
+// proxy, the transport dials the proxy and tunnels the request through it. The
+// dialer used to refuse that dial as a loopback address, so every fetch on a
+// machine behind such a proxy failed with "loopback hosts are blocked" for a
+// public target that had already been validated (#569).
+func TestWebFetchTunnelsThroughTheConfiguredProxy(t *testing.T) {
+	listener, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer listener.Close()
+	arrived := make(chan string, 1)
+	go func() {
+		conn, err := listener.Accept()
+		if err != nil {
+			return
+		}
+		defer conn.Close()
+		buffer := make([]byte, 256)
+		n, _ := conn.Read(buffer)
+		arrived <- string(buffer[:n])
+	}()
+	proxyURL, err := url.Parse("http://" + listener.Addr().String())
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	// A proxied fetch never resolves the target on this side; the CONNECT
+	// carries the hostname and the proxy resolves it.
+	transport := webFetchTransportWithProxy(t,
+		webFetchResolverFunc(func(context.Context, string, string) ([]netip.Addr, error) {
+			return nil, errors.New("resolver must not be called for a proxied fetch")
+		}),
+		func(*http.Request) (*url.URL, error) { return proxyURL, nil })
+	client := &http.Client{Transport: transport, Timeout: 3 * time.Second}
+
+	_, err = client.Get("https://public.example/resource")
+	select {
+	case first := <-arrived:
+		if line := strings.SplitN(first, "\r\n", 2)[0]; line != "CONNECT public.example:443 HTTP/1.1" {
+			t.Fatalf("proxy received %q, want a CONNECT for the target", line)
+		}
+	case <-time.After(5 * time.Second):
+		t.Fatalf("the proxy never received a connection; request error: %v", err)
+	}
+}
+
+// AND A DIRECT FETCH STAYS PINNED, EVEN WHEN ITS ORIGIN IS THE PROXY'S OWN
+// ADDRESS.
+//
+// This is the NO_PROXY shape: the proxy function sends one host direct. An
+// exemption derived from asking that function about a request of our own
+// invention would answer "proxied" for the excluded host too, and this dial
+// would skip the pin and reach whatever the name resolves to at connect time.
+func TestWebFetchDirectRequestToTheProxyEndpointIsStillPinned(t *testing.T) {
+	proxyURL, err := url.Parse("http://rebind.example:80")
+	if err != nil {
+		t.Fatal(err)
+	}
+	lookups := 0
+	transport := webFetchTransportWithProxy(t,
+		webFetchResolverFunc(func(_ context.Context, _ string, host string) ([]netip.Addr, error) {
+			lookups++
+			return []netip.Addr{netip.MustParseAddr("127.0.0.1")}, nil
+		}),
+		func(request *http.Request) (*url.URL, error) {
+			if request.URL.Hostname() == "rebind.example" {
+				return nil, nil
+			}
+			return proxyURL, nil
+		})
+	client := &http.Client{Transport: transport, Timeout: 3 * time.Second}
+
+	_, err = client.Get("http://rebind.example/data")
+
+	if lookups == 0 {
+		t.Fatal("the direct dial skipped the address pin because its address matched the configured proxy endpoint")
+	}
+	if err == nil || !strings.Contains(err.Error(), "loopback hosts are blocked") {
+		t.Fatalf("err = %v, want the private answer to be refused", err)
+	}
+}
+
+// A proxy configured with a Unicode hostname is dialed by its IDNA-encoded
+// name, and it is still the proxy.
+func TestWebFetchUnicodeProxyHostnameIsStillTheProxy(t *testing.T) {
+	dialed := ""
+	transport := webFetchTransportWithProxy(t,
+		webFetchResolverFunc(func(context.Context, string, string) ([]netip.Addr, error) {
+			return nil, errors.New("resolver must not be called for a proxied fetch")
+		}),
+		func(*http.Request) (*url.URL, error) { return url.Parse("http://büro.example:3067") })
+	guarded := transport.DialContext
+	transport.DialContext = func(ctx context.Context, network, address string) (net.Conn, error) {
+		dialed = address
+		return guarded(ctx, network, address)
+	}
+	client := &http.Client{Transport: transport, Timeout: 3 * time.Second}
+
+	_, err := client.Get("https://public.example/resource")
+
+	if dialed != "xn--bro-hoa.example:3067" {
+		t.Fatalf("SETUP INVALID: dialed %q, want the IDNA-encoded proxy endpoint", dialed)
+	}
+	if err != nil && strings.Contains(err.Error(), "hosts are blocked") {
+		t.Fatalf("the configured proxy was refused by the guard: %v", err)
+	}
+}
+
+// Without a proxy the guard is exactly what it was: loopback is refused and
+// the dialer never runs.
+func TestWebFetchSafeDialStillRefusesLoopbackWithoutAProxy(t *testing.T) {
+	dialCalled := false
+	dial := webFetchSafeDialContext(
+		webFetchResolverFunc(func(_ context.Context, network string, host string) ([]netip.Addr, error) {
+			t.Fatalf("resolver consulted for a loopback literal: network=%q host=%q", network, host)
+			return nil, nil
+		}),
+		webFetchDialFunc(func(context.Context, string, string) (net.Conn, error) {
+			dialCalled = true
+			return nil, errors.New("dial should not run")
+		}),
+	)
+
+	_, err := dial(context.Background(), "tcp", "127.0.0.1:3067")
+	if err == nil || !strings.Contains(err.Error(), "loopback hosts are blocked") {
+		t.Fatalf("expected loopback rejection, got %v", err)
+	}
+	if dialCalled {
+		t.Fatal("loopback was dialed with no proxy configured")
+	}
+}

internal/tools/web_fetch_test.go

@@ -11,6 +11,7 @@ import (
 	"strings"
 	"testing"
 
+	"github.com/Gitlawb/zero/internal/proxydial"
 	zeroSandbox "github.com/Gitlawb/zero/internal/sandbox"
 )
 
@@ -325,15 +326,26 @@ func TestWebFetchToolConfiguresDialTimeSafetyForDefaultTransport(t *testing.T) {
 	}
 
 	client := tool.clientForRun()
-	transport, ok := client.Transport.(*http.Transport)
+	// The round tripper is the route-recording wrapper, not the bare transport:
+	// it is what tells the dialer which dial is the one to the proxy the
+	// transport picked for a given request. The guarded transport it wraps
+	// stays reachable, and is what the rest of this test inspects.
+	transport, ok := client.Transport.(*proxydial.Transport)
 	if !ok {
-		t.Fatalf("client transport = %T, want *http.Transport", client.Transport)
+		t.Fatalf("client transport = %T, want *proxydial.Transport", client.Transport)
 	}
 	if transport.DialContext == nil {
 		t.Fatal("expected web_fetch transport to install a safe DialContext")
 	}
-	if transport.Proxy != nil {
-		t.Fatal("expected web_fetch transport to disable proxy resolution")
+	// REVERSED ON PURPOSE. The guarded fetch used to pin Proxy to nil as part of
+	// the SSRF hardening, and this assertion held it there. #569 is what that
+	// cost: on a machine that reaches the network only through a configured
+	// forward proxy, every fetch failed outright. The proxy is honoured now, and
+	// the wrapper hands the dialer the route chosen for each request so the one
+	// dial it lets past the guard is the one to that proxy. The target is still
+	// validated before the request, which the tests below pin.
+	if transport.Proxy == nil {
+		t.Fatal("expected web_fetch transport to honour the environment proxy; a machine behind a forward proxy cannot fetch at all without it (#569)")
 	}
 }