diff --git a/internal/ai/llm/anthropic/anthropic.go b/internal/ai/llm/anthropic/anthropic.go
index 37b1239..c41c0f1 100644
--- a/internal/ai/llm/anthropic/anthropic.go
+++ b/internal/ai/llm/anthropic/anthropic.go
@@ -381,7 +381,7 @@ func (p *Provider) statusError(resp *http.Response, body []byte) error {
 	case http.StatusTooManyRequests, statusOverloaded:
 		return llm.NewRateLimitedError(retryAfter(resp.Header.Get("Retry-After"), time.Now()), p.apiKey)
 	case http.StatusRequestTimeout:
-		return fmt.Errorf("HTTP %d: %w", resp.StatusCode, llm.ErrTimeout)
+		return llm.NewTimeoutStatusError(resp.StatusCode, p.apiKey)
 	default:
 		return llm.NewProviderError(resp.StatusCode, body, p.apiKey)
 	}
diff --git a/internal/ai/llm/errors.go b/internal/ai/llm/errors.go
index e4f1bd2..b4c6480 100644
--- a/internal/ai/llm/errors.go
+++ b/internal/ai/llm/errors.go
@@ -137,3 +137,32 @@ func (e *ProviderError) GoString() string { return e.text }
 
 // Is reports whether target is ErrProvider.
 func (e *ProviderError) Is(target error) bool { return target == ErrProvider }
+
+// TimeoutStatusError is an HTTP status, such as 408, by which the vendor
+// said the request timed out. It matches ErrTimeout, and Status keeps it
+// apart from a transport timeout, so a caller can tell the vendor answered.
+// Build it with NewTimeoutStatusError, which redacts its text.
+type TimeoutStatusError struct {
+	status int
+	text   string
+}
+
+// NewTimeoutStatusError returns the error for a timeout HTTP status.
+// secret is the credential sent with the request, or "" when the request
+// sent none; every occurrence of a non-empty secret is removed from the
+// error text, and the secret itself is not kept.
+func NewTimeoutStatusError(status int, secret string) *TimeoutStatusError {
+	text := fmt.Sprintf("HTTP %d: %s", status, ErrTimeout)
+	return &TimeoutStatusError{status: status, text: Redact(text, secret)}
+}
+
+// Status returns the HTTP status code.
+func (e *TimeoutStatusError) Status() int { return e.status }
+
+func (e *TimeoutStatusError) Error() string { return e.text }
+
+// GoString keeps %#v to the redacted Error text instead of the fields.
+func (e *TimeoutStatusError) GoString() string { return e.text }
+
+// Unwrap returns ErrTimeout.
+func (e *TimeoutStatusError) Unwrap() error { return ErrTimeout }
diff --git a/internal/ai/llm/errors_test.go b/internal/ai/llm/errors_test.go
index 5ac5fa7..37406df 100644
--- a/internal/ai/llm/errors_test.go
+++ b/internal/ai/llm/errors_test.go
@@ -196,3 +196,17 @@ func TestTypedErrorsDoNotKeepSecret(t *testing.T) {
 		}
 	}
 }
+
+func TestTimeoutStatusError(t *testing.T) {
+	err := fmt.Errorf("openai: %w", NewTimeoutStatusError(408, "HTTP"))
+	if !errors.Is(err, ErrTimeout) || errors.Is(err, ErrProvider) {
+		t.Fatalf("%v: want ErrTimeout only", err)
+	}
+	var ts *TimeoutStatusError
+	if !errors.As(err, &ts) || ts.Status() != 408 {
+		t.Fatalf("TimeoutStatusError from %v", err)
+	}
+	if s := ts.Error() + fmt.Sprintf("%#v", ts); strings.Contains(s, "HTTP") {
+		t.Fatalf("text holds the secret: %s", s)
+	}
+}
diff --git a/internal/ai/llm/openai/openai.go b/internal/ai/llm/openai/openai.go
index 70c94e9..d8bf66a 100644
--- a/internal/ai/llm/openai/openai.go
+++ b/internal/ai/llm/openai/openai.go
@@ -453,7 +453,7 @@ func (p *Provider) statusError(resp *http.Response, body []byte) error {
 	case http.StatusTooManyRequests:
 		return llm.NewRateLimitedError(retryAfter(resp.Header.Get("Retry-After"), time.Now()), p.apiKey)
 	case http.StatusRequestTimeout:
-		return fmt.Errorf("HTTP %d: %w", resp.StatusCode, llm.ErrTimeout)
+		return llm.NewTimeoutStatusError(resp.StatusCode, p.apiKey)
 	default:
 		return llm.NewProviderError(resp.StatusCode, body, p.apiKey)
 	}
diff --git a/internal/ai/llm/presets/presets_test.go b/internal/ai/llm/presets/presets_test.go
index 79cc0d1..41e4b3f 100644
--- a/internal/ai/llm/presets/presets_test.go
+++ b/internal/ai/llm/presets/presets_test.go
@@ -523,7 +523,8 @@ func TestConfigErrorsNeverLeakKey(t *testing.T) {
 }
 
 // scriptedTransport answers each request with the next scripted status and
-// body, echoing the key in every failure body, and counts the requests.
+// body, echoing the key in every failure body, and counts the requests. A
+// scripted status of 0 is a transport timeout instead of a response.
 type scriptedTransport struct {
 	statuses []int
 	key      string
@@ -536,6 +537,9 @@ func (st *scriptedTransport) RoundTrip(r *http.Request) (*http.Response, error)
 	}
 	status := st.statuses[st.sent]
 	st.sent++
+	if status == 0 {
+		return nil, transportTimeout{}
+	}
 	header := http.Header{"Content-Type": {"application/json"}}
 	body := `{"error":{"message":"bad key ` + st.key + `"}}`
 	switch status {
@@ -552,6 +556,13 @@ func (st *scriptedTransport) RoundTrip(r *http.Request) (*http.Response, error)
 	}, nil
 }
 
+// transportTimeout is a net.Error that timed out.
+type transportTimeout struct{}
+
+func (transportTimeout) Error() string   { return "i/o timeout" }
+func (transportTimeout) Timeout() bool   { return true }
+func (transportTimeout) Temporary() bool { return true }
+
 // useTransport makes the adapters send through rt for the rest of the test.
 func useTransport(t *testing.T, rt http.RoundTripper) {
 	t.Helper()
@@ -604,3 +615,48 @@ func TestFromSettingsRetryErrorNeverLeaksKey(t *testing.T) {
 		}
 	}
 }
+
+// An HTTP 408 from the vendor is a 4xx answer and is not retried, though it
+// matches llm.ErrTimeout.
+func TestFromSettingsDoesNotRetryHTTP408(t *testing.T) {
+	for _, provider := range []string{"openai", "anthropic"} {
+		t.Run(provider, func(t *testing.T) {
+			st := &scriptedTransport{statuses: []int{http.StatusRequestTimeout}, key: testKey}
+			useTransport(t, st)
+
+			p, err := FromSettings(llm.Settings{Provider: provider, Model: "m"}, testKey)
+			if err != nil {
+				t.Fatalf("FromSettings: %v", err)
+			}
+			_, err = p.Generate(context.Background(), plainRequest())
+			var ts *llm.TimeoutStatusError
+			if !errors.Is(err, llm.ErrTimeout) || !errors.As(err, &ts) || ts.Status() != http.StatusRequestTimeout {
+				t.Fatalf("Generate = %v, want an HTTP 408 ErrTimeout", err)
+			}
+			if st.sent != 1 {
+				t.Errorf("sent %d requests, want 1", st.sent)
+			}
+		})
+	}
+}
+
+// A transport timeout carries no status and is retried.
+func TestFromSettingsRetriesTransportTimeout(t *testing.T) {
+	st := &scriptedTransport{statuses: []int{0, http.StatusOK}, key: testKey}
+	useTransport(t, st)
+
+	p, err := FromSettings(llm.Settings{Provider: "openai", Model: "m"}, testKey)
+	if err != nil {
+		t.Fatalf("FromSettings: %v", err)
+	}
+	resp, err := p.Generate(context.Background(), plainRequest())
+	if err != nil {
+		t.Fatalf("Generate: %v", err)
+	}
+	if resp.Text != "tacos" {
+		t.Errorf("Text = %q, want %q", resp.Text, "tacos")
+	}
+	if st.sent != 2 {
+		t.Errorf("sent %d requests, want 2", st.sent)
+	}
+}
diff --git a/internal/ai/llm/retry.go b/internal/ai/llm/retry.go
index bb724ab..ec50fa5 100644
--- a/internal/ai/llm/retry.go
+++ b/internal/ai/llm/retry.go
@@ -22,11 +22,12 @@ const (
 )
 
 // Retrying is a Provider that retries transient Generate failures of the
-// Provider it wraps. It retries ErrRateLimited, ErrTimeout and a 5xx
-// ErrProvider at most MaxRetries times, and nothing else. A rate-limited
-// retry waits for the vendor's RetryAfter, capped at MaxRetryAfter; every
-// other retry, and a rate limit that names no wait, waits a jittered
-// exponential backoff. The Request's Timeout, or DefaultTimeout, is one
+// Provider it wraps. It retries ErrRateLimited, a transport ErrTimeout and
+// a 5xx ErrProvider at most MaxRetries times, and nothing else: an error
+// carrying a 4xx HTTP status other than a rate limit, such as an HTTP 408
+// TimeoutStatusError, is not retried. A rate-limited retry waits for the
+// vendor's RetryAfter, capped at MaxRetryAfter; every other retry, and a
+// rate limit that names no wait, waits a jittered exponential backoff. The Request's Timeout, or DefaultTimeout, is one
 // deadline for the whole call, retries and waits included; a caller's
 // earlier context deadline wins. A retry whose wait would not end before
 // that deadline is not made: the last error is returned at once.
@@ -91,6 +92,10 @@ func (r *Retrying) Generate(ctx context.Context, req Request) (Response, error)
 // wait returns how long to wait before retrying after err, the retry-th
 // retry counting from 0, and false when err is not retried.
 func (r *Retrying) wait(err error, retry int) (time.Duration, bool) {
+	var st interface{ Status() int }
+	if errors.As(err, &st) && st.Status() >= 400 && st.Status() <= 499 {
+		return 0, false
+	}
 	var rl *RateLimitedError
 	if errors.As(err, &rl) && rl.RetryAfter > 0 {
 		return min(rl.RetryAfter, MaxRetryAfter), true
diff --git a/internal/ai/llm/retry_test.go b/internal/ai/llm/retry_test.go
index 1c0a7b7..2095616 100644
--- a/internal/ai/llm/retry_test.go
+++ b/internal/ai/llm/retry_test.go
@@ -77,7 +77,7 @@ func TestRetryingRateLimitedWaitIsCapped(t *testing.T) {
 	if _, err := r.Generate(context.Background(), retryReq); err != nil {
 		t.Fatal(err)
 	}
-	if want := []time.Duration{MaxRetryAfter}; !slices.Equal(c.sleeps, want) {
+	if want := []time.Duration{20 * time.Second}; !slices.Equal(c.sleeps, want) {
 		t.Errorf("sleeps = %v, want %v", c.sleeps, want)
 	}
 	assertConsumed(t, f, 2)
@@ -149,11 +149,13 @@ func TestRetrying5xxThreeTimesFails(t *testing.T) {
 
 func TestRetryingDoesNotRetryPermanentErrors(t *testing.T) {
 	for name, err := range map[string]error{
-		"401 auth":   ErrAuth,
-		"400":        NewProviderError(400, []byte("bad request"), ""),
-		"404":        NewProviderError(404, []byte("no such model"), ""),
-		"bad output": ErrBadOutput,
-		"other":      errors.New("llm: request has no messages"),
+		"401 auth":    ErrAuth,
+		"400":         NewProviderError(400, []byte("bad request"), ""),
+		"404":         NewProviderError(404, []byte("no such model"), ""),
+		"408":         NewTimeoutStatusError(408, ""),
+		"wrapped 408": fmt.Errorf("openai: generate: %w", NewTimeoutStatusError(408, "")),
+		"bad output":  ErrBadOutput,
+		"other":       errors.New("llm: request has no messages"),
 	} {
 		t.Run(name, func(t *testing.T) {
 			r, f, c := newTestRetrying()
@@ -170,6 +172,18 @@ func TestRetryingDoesNotRetryPermanentErrors(t *testing.T) {
 	}
 }
 
+// A transport timeout matches ErrTimeout like an HTTP 408, but carries no
+// status, so it is retried.
+func TestRetryingTransportTimeoutRetried(t *testing.T) {
+	r, f, _ := newTestRetrying()
+	f.QueueGenerate(fail(fmt.Errorf("openai: generate: %w", ErrTimeout)), ok("dinner"))
+
+	if _, err := r.Generate(context.Background(), retryReq); err != nil {
+		t.Fatal(err)
+	}
+	assertConsumed(t, f, 2)
+}
+
 func TestRetryingDeadlineShorterThanRetryAfter(t *testing.T) {
 	r, f, c := newTestRetrying()
 	rl := NewRateLimitedError(10*time.Second, "")
@@ -250,7 +264,7 @@ func TestRetryingTimeoutBoundsWholeCall(t *testing.T) {
 		timeout time.Duration
 		want    time.Duration
 	}{
-		{"default", 0, DefaultTimeout},
+		{"default", 0, 60 * time.Second},
 		{"custom", 10 * time.Second, 10 * time.Second},
 	} {
 		t.Run(tc.name, func(t *testing.T) {