test(cli): fail when the prewarm hold gives up

The bounded wait let the turn proceed after its guard expired, so a probe that
arrived late still left the count at 1 and the test passed. That proves the
probe was eventually received, not that it preceded the turn, which is the only
thing this test claims. Raised by CodeRabbit.

The expiry is now recorded and checked before the count, since the count cannot
tell the two apart.

Verified by suppressing the probe, which makes the guard expire: the assertion
fires with its own message rather than the count assertion, and the run takes
the full guard duration.

internal/cli/exec_turn_session_test.go

@@ -5,6 +5,7 @@ import (
 	"net/http"
 	"net/http/httptest"
 	"strings"
+	"sync"
 	"sync/atomic"
 	"testing"
 	"time"
@@ -24,12 +25,47 @@ func TestRunExecOptimizedSessionUnderGate(t *testing.T) {
 	cwd := t.TempDir()
 
 	var heads, posts atomic.Int64
+	// Closed when the prewarm probe lands, so the turn can be held open until it
+	// does. See the POST handler for why that ordering has to be forced.
+	headSeen := make(chan struct{})
+	var headOnce sync.Once
+	var prewarmWaitTimedOut atomic.Bool
 	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		switch {
 		case r.Method == http.MethodHead:
 			heads.Add(1)
+			headOnce.Do(func() { close(headSeen) })
 			w.WriteHeader(http.StatusMethodNotAllowed)
 		case r.Method == http.MethodPost && strings.HasSuffix(r.URL.Path, "/chat/completions"):
+			// Hold the turn open until the prewarm probe arrives. The probe is
+			// issued on the run's context, and runExec cancels that context the
+			// moment it returns, because the stop function signalContext hands
+			// back is a CancelFunc. A probe that has not reached the wire by the
+			// end of the run therefore never reaches it at all. That is why the
+			// poll this replaced could not work at any deadline: once the run is
+			// over the probe is cancelled, not merely slow.
+			//
+			// This widens the window, it does not close it. Once the goroutine is
+			// scheduled it still has only prewarmTimeout to dial loopback and
+			// write the request, and that timeout is armed inside the goroutine
+			// itself, so holding the turn here cannot extend it. If this test
+			// ever fails again, prewarmTimeout is where to look, not this hold.
+			//
+			// No self-deadlock: the pinned transport leaves MaxConnsPerHost at 0,
+			// so the HEAD dials its own connection instead of queueing behind
+			// this held POST. Do not set a per-host connection limit there.
+			//
+			// Bounded, so a probe that genuinely never fires fails the assertion
+			// below with a useful message instead of hanging the test.
+			select {
+			case <-headSeen:
+			case <-time.After(10 * time.Second):
+				// Record it. A probe that shows up after this gave up would still
+				// leave heads at 1, so the count alone proves the probe was
+				// eventually received, not that it was ordered before the turn,
+				// which is the whole claim of this test.
+				prewarmWaitTimedOut.Store(true)
+			}
 			posts.Add(1)
 			w.Header().Set("Content-Type", "text/event-stream")
 			_, _ = w.Write([]byte("data: {\"choices\":[{\"delta\":{\"content\":\"done\"}}]}\n\n"))
@@ -75,14 +111,13 @@ func TestRunExecOptimizedSessionUnderGate(t *testing.T) {
 	if got := posts.Load(); got < 1 {
 		t.Fatalf("server saw %d chat-completions POSTs, want >= 1", got)
 	}
-	// The prewarm probe is asynchronous; it fires well before the model turn
-	// finishes, but poll rather than assuming scheduling order. The deadline
-	// exceeds the production prewarmTimeout (3s) so a slow probe cannot flake
-	// this assertion.
-	deadline := time.Now().Add(5 * time.Second)
-	for heads.Load() == 0 && time.Now().Before(deadline) {
-		time.Sleep(10 * time.Millisecond)
+	// Checked before the count, because the count cannot tell the two apart: a
+	// probe that arrived only after the guard expired still leaves heads at 1.
+	if prewarmWaitTimedOut.Load() {
+		t.Fatal("the turn was not held until the prewarm probe arrived; the probe did not precede it")
 	}
+	// No polling: the turn above could not complete until the probe landed, so
+	// the count is settled by this point.
 	if got := heads.Load(); got != 1 {
 		t.Fatalf("server saw %d prewarm HEAD probes, want exactly 1", got)
 	}