Do not retry an HTTP 408; lock retry cap and timeout values

The OpenAI and Anthropic adapters now report an HTTP 408 as
llm.TimeoutStatusError, which still matches llm.ErrTimeout but carries
its status. Retrying no longer retries any error carrying a 4xx status,
so a vendor's 408 is returned at once while a transport timeout, which
has no status, is still retried.

Tests: 408 (bare and wrapped) is not retried and a transport timeout is;
FromSettings integration cases for an OpenAI and Anthropic 408 and an
OpenAI transport timeout; the cap and default-timeout tests assert the
literal 20 s and 60 s instead of the constants they lock.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

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)
 	}

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 }

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)
+	}
+}

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)
 	}

internal/ai/llm/presets/presets.go

@@ -178,13 +178,14 @@ var all = map[string]Preset{
 //
 // The Provider sends s.Temperature with every request whose Temperature is
 // nil; a request that sets one keeps it. Neither is sent to a model the
-// preset's OmitTemperature matches.
+// preset's OmitTemperature matches. It is wrapped in llm.NewRetrying, so
+// Generate retries transient vendor failures and has the default timeout.
 func FromSettings(s llm.Settings, key string) (llm.Provider, error) {
 	cp, err := fromSettings(s, key)
 	if err != nil {
 		return nil, redact(err, key)
 	}
-	return cp, nil
+	return llm.NewRetrying(cp), nil
 }
 
 func fromSettings(s llm.Settings, key string) (*configured, error) {

internal/ai/llm/presets/presets_test.go

@@ -22,10 +22,8 @@ type captured struct {
 	body   map[string]json.RawMessage
 }
 
-var errStop = errors.New("recorded")
-
-// recordingTransport records each request and fails it, so no request
-// leaves the process.
+// recordingTransport records each request and answers it 400, so no
+// request leaves the process and the Provider never retries it.
 type recordingTransport struct{ reqs []captured }
 
 func (rt *recordingTransport) RoundTrip(r *http.Request) (*http.Response, error) {
@@ -40,7 +38,12 @@ func (rt *recordingTransport) RoundTrip(r *http.Request) (*http.Response, error)
 		}
 	}
 	rt.reqs = append(rt.reqs, c)
-	return nil, errStop
+	return &http.Response{
+		StatusCode: http.StatusBadRequest,
+		Header:     http.Header{"Content-Type": {"application/json"}},
+		Body:       io.NopCloser(strings.NewReader(`{}`)),
+		Request:    r,
+	}, nil
 }
 
 // generate builds the provider s describes and returns the request its
@@ -327,7 +330,7 @@ func TestNegativeTemperatureRejectedForRejectingModels(t *testing.T) {
 		}
 		req := plainRequest()
 		req.Temperature = ptr(-0.5)
-		if _, err := p.Generate(context.Background(), req); err == nil || errors.Is(err, errStop) || !strings.Contains(err.Error(), "temperature") {
+		if _, err := p.Generate(context.Background(), req); err == nil || errors.Is(err, llm.ErrProvider) || !strings.Contains(err.Error(), "temperature") {
 			t.Errorf("%s: Generate = %v, want a temperature validation error", s.Model, err)
 		}
 	}
@@ -465,7 +468,7 @@ func TestGenerateValidationErrorsNeverLeakKey(t *testing.T) {
 		req := plainRequest()
 		req.Temperature = ptr(-0.5)
 		_, err = p.Generate(context.Background(), req)
-		if err == nil || errors.Is(err, errStop) {
+		if err == nil || errors.Is(err, llm.ErrProvider) {
 			t.Fatalf("%s: Generate = %v, want a validation error", key, err)
 		}
 		for e := error(err); e != nil; e = errors.Unwrap(e) {
@@ -518,3 +521,142 @@ 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. A
+// scripted status of 0 is a transport timeout instead of a response.
+type scriptedTransport struct {
+	statuses []int
+	key      string
+	sent     int
+}
+
+func (st *scriptedTransport) RoundTrip(r *http.Request) (*http.Response, error) {
+	if st.sent == len(st.statuses) {
+		return nil, fmt.Errorf("unscripted request %d", st.sent+1)
+	}
+	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 {
+	case http.StatusOK:
+		body = `{"model":"m","choices":[{"message":{"content":"tacos"},"finish_reason":"stop"}]}`
+	case http.StatusTooManyRequests:
+		header.Set("Retry-After", "1")
+	}
+	return &http.Response{
+		StatusCode: status,
+		Header:     header,
+		Body:       io.NopCloser(strings.NewReader(body)),
+		Request:    r,
+	}, 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()
+	orig := http.DefaultTransport
+	http.DefaultTransport = rt
+	t.Cleanup(func() { http.DefaultTransport = orig })
+}
+
+// The Provider FromSettings returns retries a rate-limited Generate.
+func TestFromSettingsRetriesRateLimited(t *testing.T) {
+	st := &scriptedTransport{statuses: []int{http.StatusTooManyRequests, 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)
+	}
+}
+
+// When every retry fails, the error FromSettings's Provider returns keeps
+// its sentinel and never holds the key the vendor echoed.
+func TestFromSettingsRetryErrorNeverLeaksKey(t *testing.T) {
+	st := &scriptedTransport{statuses: []int{http.StatusTooManyRequests, http.StatusTooManyRequests, http.StatusServiceUnavailable}, key: testKey}
+	useTransport(t, st)
+
+	p, err := FromSettings(llm.Settings{Provider: "openai", Model: "m"}, testKey)
+	if err != nil {
+		t.Fatalf("FromSettings: %v", err)
+	}
+	_, err = p.Generate(context.Background(), plainRequest())
+	if !errors.Is(err, llm.ErrProvider) {
+		t.Fatalf("Generate = %v, want %v", err, llm.ErrProvider)
+	}
+	if st.sent != llm.MaxRetries+1 {
+		t.Errorf("sent %d requests, want %d", st.sent, llm.MaxRetries+1)
+	}
+	for e := error(err); e != nil; e = errors.Unwrap(e) {
+		if s := e.Error() + fmt.Sprintf("%#v", e); strings.Contains(s, testKey) {
+			t.Fatalf("error leaks the key: %s", s)
+		}
+	}
+}
+
+// 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)
+	}
+}

internal/ai/llm/retry.go

@@ -0,0 +1,124 @@
+package llm
+
+import (
+	"context"
+	"errors"
+	"math/rand/v2"
+	"time"
+)
+
+const (
+	// DefaultTimeout bounds a whole Generate call, retries and waits
+	// included, whose Request sets no Timeout.
+	DefaultTimeout = 60 * time.Second
+	// MaxRetries is how many times a failed Generate is retried, so a call
+	// makes at most MaxRetries+1 attempts.
+	MaxRetries = 2
+	// MaxRetryAfter caps the wait a rate-limited vendor may ask for.
+	MaxRetryAfter = 20 * time.Second
+	// backoffBase is the first retry's backoff before jitter; each later
+	// retry doubles it.
+	backoffBase = time.Second
+)
+
+// Retrying is a Provider that retries transient Generate failures of the
+// 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.
+// ListModels and Verify pass straight through.
+type Retrying struct {
+	Provider
+	// now is the clock; tests replace it.
+	now func() time.Time
+	// sleep waits d or until ctx is done; tests replace it.
+	sleep func(ctx context.Context, d time.Duration) error
+	// jitter returns a random duration in [0, n) for n > 0; tests replace
+	// it.
+	jitter func(n time.Duration) time.Duration
+}
+
+// NewRetrying returns inner wrapped with retries and the default Generate
+// timeout.
+func NewRetrying(inner Provider) *Retrying {
+	return &Retrying{
+		Provider: inner,
+		now:      time.Now,
+		sleep:    sleep,
+		jitter:   rand.N[time.Duration],
+	}
+}
+
+// Generate sends req to the wrapped Provider, retrying transient failures.
+// req.Timeout, or DefaultTimeout when it is 0, sets one deadline for the
+// whole call, carried by the context each attempt receives; attempts get
+// req with Timeout 0 so none restarts the clock.
+func (r *Retrying) Generate(ctx context.Context, req Request) (Response, error) {
+	timeout := req.Timeout
+	if timeout == 0 {
+		timeout = DefaultTimeout
+	}
+	if timeout > 0 {
+		// A negative Timeout stays on req for the wrapped Provider's
+		// Validate to reject, with its key redaction.
+		req.Timeout = 0
+	}
+	ctx, cancel := context.WithDeadline(ctx, r.now().Add(timeout))
+	defer cancel()
+	deadline, _ := ctx.Deadline()
+	for retry := 0; ; retry++ {
+		resp, err := r.Provider.Generate(ctx, req)
+		if err == nil || retry == MaxRetries || ctx.Err() != nil {
+			return resp, err
+		}
+		wait, ok := r.wait(err, retry)
+		if !ok {
+			return resp, err
+		}
+		if !r.now().Add(wait).Before(deadline) {
+			return resp, err
+		}
+		if serr := r.sleep(ctx, wait); serr != nil {
+			return resp, err
+		}
+	}
+}
+
+// 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
+	}
+	var pe *ProviderError
+	switch {
+	case errors.Is(err, ErrRateLimited), errors.Is(err, ErrTimeout):
+	case errors.As(err, &pe) && pe.Status() >= 500 && pe.Status() <= 599:
+	default:
+		return 0, false
+	}
+	half := (backoffBase << retry) / 2
+	return half + r.jitter(half), true
+}
+
+// sleep waits d or until ctx is done, returning ctx's error in that case.
+func sleep(ctx context.Context, d time.Duration) error {
+	t := time.NewTimer(d)
+	defer t.Stop()
+	select {
+	case <-t.C:
+		return nil
+	case <-ctx.Done():
+		return ctx.Err()
+	}
+}

internal/ai/llm/retry_test.go

@@ -0,0 +1,359 @@
+package llm
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"slices"
+	"testing"
+	"time"
+)
+
+// fakeClock is a clock whose sleeps return at once, advance it and are
+// recorded.
+type fakeClock struct {
+	t      time.Time
+	sleeps []time.Duration
+}
+
+func (c *fakeClock) now() time.Time { return c.t }
+
+func (c *fakeClock) sleep(ctx context.Context, d time.Duration) error {
+	if err := ctx.Err(); err != nil {
+		return err
+	}
+	c.sleeps = append(c.sleeps, d)
+	c.t = c.t.Add(d)
+	return nil
+}
+
+// newTestRetrying returns a Retrying over a fresh Fake with a fake clock
+// at the real current time, so real context deadlines compare sensibly,
+// and jitter that always returns its maximum.
+func newTestRetrying() (*Retrying, *Fake, *fakeClock) {
+	f := &Fake{}
+	c := &fakeClock{t: time.Now()}
+	r := NewRetrying(f)
+	r.now = c.now
+	r.sleep = c.sleep
+	r.jitter = func(n time.Duration) time.Duration { return n - 1 }
+	return r, f, c
+}
+
+var retryReq = Request{Messages: []Message{{Role: RoleUser, Content: "plan dinners"}}}
+
+func ok(text string) GenerateResult { return GenerateResult{Response: Response{Text: text}} }
+
+func fail(err error) GenerateResult { return GenerateResult{Err: err} }
+
+func assertConsumed(t *testing.T, f *Fake, attempts int) {
+	t.Helper()
+	if g, _, _ := f.Remaining(); g != 0 {
+		t.Errorf("%d scripted Generate results unused", g)
+	}
+	if n := len(f.Requests()); n != attempts {
+		t.Errorf("made %d attempts, want %d", n, attempts)
+	}
+}
+
+func TestRetryingRateLimitedThenSuccess(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(fail(NewRateLimitedError(3*time.Second, "")), ok("dinner"))
+
+	resp, err := r.Generate(context.Background(), retryReq)
+	if err != nil || resp.Text != "dinner" {
+		t.Fatalf("Generate = %+v, %v", resp, err)
+	}
+	if want := []time.Duration{3 * time.Second}; !slices.Equal(c.sleeps, want) {
+		t.Errorf("sleeps = %v, want %v", c.sleeps, want)
+	}
+	assertConsumed(t, f, 2)
+}
+
+func TestRetryingRateLimitedWaitIsCapped(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(fail(NewRateLimitedError(time.Hour, "")), ok("dinner"))
+
+	if _, err := r.Generate(context.Background(), retryReq); err != nil {
+		t.Fatal(err)
+	}
+	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)
+}
+
+func TestRetryingRateLimitedWithoutRetryAfterBacksOff(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(fail(NewRateLimitedError(0, "")), ok("dinner"))
+
+	if _, err := r.Generate(context.Background(), retryReq); err != nil {
+		t.Fatal(err)
+	}
+	if want := []time.Duration{time.Second - 1}; !slices.Equal(c.sleeps, want) {
+		t.Errorf("sleeps = %v, want %v", c.sleeps, want)
+	}
+}
+
+func TestRetrying5xxTwiceThenSuccess(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(
+		fail(NewProviderError(503, []byte("busy"), "")),
+		// Adapters wrap the error they return.
+		fail(fmt.Errorf("openai: generate: %w", NewProviderError(503, []byte("busy"), ""))),
+		ok("dinner"),
+	)
+
+	resp, err := r.Generate(context.Background(), retryReq)
+	if err != nil || resp.Text != "dinner" {
+		t.Fatalf("Generate = %+v, %v", resp, err)
+	}
+	// Max jitter: [0.5 s, 1 s) then [1 s, 2 s).
+	if want := []time.Duration{time.Second - 1, 2*time.Second - 1}; !slices.Equal(c.sleeps, want) {
+		t.Errorf("sleeps = %v, want %v", c.sleeps, want)
+	}
+	assertConsumed(t, f, 3)
+}
+
+func TestRetryingBackoffJitterLowerBound(t *testing.T) {
+	r, f, c := newTestRetrying()
+	r.jitter = func(time.Duration) time.Duration { return 0 }
+	f.QueueGenerate(fail(ErrTimeout), fail(ErrTimeout), ok("dinner"))
+
+	if _, err := r.Generate(context.Background(), retryReq); err != nil {
+		t.Fatal(err)
+	}
+	if want := []time.Duration{500 * time.Millisecond, time.Second}; !slices.Equal(c.sleeps, want) {
+		t.Errorf("sleeps = %v, want %v", c.sleeps, want)
+	}
+}
+
+func TestRetrying5xxThreeTimesFails(t *testing.T) {
+	r, f, c := newTestRetrying()
+	last := NewProviderError(503, []byte("third"), "")
+	f.QueueGenerate(
+		fail(NewProviderError(503, []byte("first"), "")),
+		fail(NewProviderError(503, []byte("second"), "")),
+		fail(last),
+	)
+
+	_, err := r.Generate(context.Background(), retryReq)
+	if err != last {
+		t.Fatalf("err = %v, want the last attempt's error", err)
+	}
+	if len(c.sleeps) != MaxRetries {
+		t.Errorf("slept %d times, want %d", len(c.sleeps), MaxRetries)
+	}
+	assertConsumed(t, f, 3)
+}
+
+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"), ""),
+		"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()
+			f.QueueGenerate(fail(err))
+
+			if _, got := r.Generate(context.Background(), retryReq); got != err {
+				t.Fatalf("err = %v, want %v", got, err)
+			}
+			if len(c.sleeps) != 0 {
+				t.Errorf("slept %v", c.sleeps)
+			}
+			assertConsumed(t, f, 1)
+		})
+	}
+}
+
+// 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, "")
+	f.QueueGenerate(fail(rl))
+	ctx, cancel := context.WithDeadline(context.Background(), c.t.Add(5*time.Second))
+	defer cancel()
+
+	if _, err := r.Generate(ctx, retryReq); err != rl {
+		t.Fatalf("err = %v, want the rate-limited error", err)
+	}
+	if len(c.sleeps) != 0 {
+		t.Errorf("slept %v", c.sleeps)
+	}
+	assertConsumed(t, f, 1)
+}
+
+func TestRetryingDeadlineShorterThanBackoff(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(fail(ErrTimeout))
+	// The first backoff with maximum jitter is just under 1 s.
+	ctx, cancel := context.WithDeadline(context.Background(), c.t.Add(time.Second-1))
+	defer cancel()
+
+	if _, err := r.Generate(ctx, retryReq); !errors.Is(err, ErrTimeout) {
+		t.Fatalf("err = %v, want ErrTimeout", err)
+	}
+	if len(c.sleeps) != 0 {
+		t.Errorf("slept %v", c.sleeps)
+	}
+	assertConsumed(t, f, 1)
+}
+
+func TestRetryingRetriesWithinDeadline(t *testing.T) {
+	r, f, c := newTestRetrying()
+	f.QueueGenerate(fail(NewRateLimitedError(3*time.Second, "")), ok("dinner"))
+	ctx, cancel := context.WithDeadline(context.Background(), c.t.Add(time.Minute))
+	defer cancel()
+
+	if _, err := r.Generate(ctx, retryReq); err != nil {
+		t.Fatal(err)
+	}
+	assertConsumed(t, f, 2)
+}
+
+func TestRetryingStopsWhenContextDone(t *testing.T) {
+	r, f, _ := newTestRetrying()
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel()
+	f.QueueGenerate(fail(ErrTimeout))
+
+	if _, err := r.Generate(ctx, retryReq); !errors.Is(err, ErrTimeout) {
+		t.Fatalf("err = %v, want ErrTimeout", err)
+	}
+	assertConsumed(t, f, 1)
+}
+
+// slowProvider is a Provider whose every attempt takes d on clock c,
+// records the deadline of the context it received, and times out.
+type slowProvider struct {
+	Provider
+	c         *fakeClock
+	d         time.Duration
+	reqs      []Request
+	deadlines []time.Time
+}
+
+func (p *slowProvider) Generate(ctx context.Context, req Request) (Response, error) {
+	p.reqs = append(p.reqs, req)
+	deadline, _ := ctx.Deadline()
+	p.deadlines = append(p.deadlines, deadline)
+	p.c.t = p.c.t.Add(p.d)
+	return Response{}, ErrTimeout
+}
+
+func TestRetryingTimeoutBoundsWholeCall(t *testing.T) {
+	for _, tc := range []struct {
+		name    string
+		timeout time.Duration
+		want    time.Duration
+	}{
+		{"default", 0, 60 * time.Second},
+		{"custom", 10 * time.Second, 10 * time.Second},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			r, _, c := newTestRetrying()
+			// Each attempt uses most of the one deadline, so a fresh full
+			// timeout per attempt would allow every retry; one deadline
+			// leaves room for exactly one.
+			p := &slowProvider{c: c, d: tc.want * 5 / 6}
+			r.Provider = p
+			start := c.t
+			req := retryReq
+			req.Timeout = tc.timeout
+
+			if _, err := r.Generate(context.Background(), req); !errors.Is(err, ErrTimeout) {
+				t.Fatalf("err = %v, want ErrTimeout", err)
+			}
+			if len(p.deadlines) != 2 {
+				t.Fatalf("made %d attempts, want 2", len(p.deadlines))
+			}
+			for i, d := range p.deadlines {
+				if !d.Equal(start.Add(tc.want)) {
+					t.Errorf("attempt %d deadline = start+%v, want start+%v", i, d.Sub(start), tc.want)
+				}
+				if p.reqs[i].Timeout != 0 {
+					t.Errorf("attempt %d Timeout = %v, want 0", i, p.reqs[i].Timeout)
+				}
+			}
+			if want := []time.Duration{time.Second - 1}; !slices.Equal(c.sleeps, want) {
+				t.Errorf("sleeps = %v, want %v", c.sleeps, want)
+			}
+		})
+	}
+}
+
+func TestRetryingCallerDeadlineShorterThanTimeout(t *testing.T) {
+	r, _, c := newTestRetrying()
+	p := &slowProvider{c: c, d: time.Second}
+	r.Provider = p
+	ctx, cancel := context.WithDeadline(context.Background(), c.t.Add(5*time.Second))
+	defer cancel()
+
+	if _, err := r.Generate(ctx, retryReq); !errors.Is(err, ErrTimeout) {
+		t.Fatalf("err = %v, want ErrTimeout", err)
+	}
+	for i, d := range p.deadlines {
+		if want, _ := ctx.Deadline(); !d.Equal(want) {
+			t.Errorf("attempt %d deadline = %v, want caller's %v", i, d, want)
+		}
+	}
+}
+
+func TestRetryingRejectsNegativeTimeout(t *testing.T) {
+	r, f, _ := newTestRetrying()
+	f.QueueGenerate(fail(errors.New("llm: timeout is negative")))
+	req := retryReq
+	req.Timeout = -time.Second
+
+	if _, err := r.Generate(context.Background(), req); err == nil {
+		t.Fatal("Generate accepted a negative timeout")
+	}
+	assertConsumed(t, f, 1)
+	if got := f.Requests()[0].Timeout; got != -time.Second {
+		t.Errorf("wrapped Provider got Timeout %v, want -1s to reject", got)
+	}
+}
+
+func TestRetryingPassesThroughListModelsAndVerify(t *testing.T) {
+	r, f, _ := newTestRetrying()
+	f.QueueListModels(ListModelsResult{Err: ErrTimeout})
+	f.QueueVerify(ErrTimeout)
+
+	if _, err := r.ListModels(context.Background()); !errors.Is(err, ErrTimeout) {
+		t.Fatalf("ListModels err = %v", err)
+	}
+	if err := r.Verify(context.Background()); !errors.Is(err, ErrTimeout) {
+		t.Fatalf("Verify err = %v", err)
+	}
+	if _, l, v := f.Remaining(); l != 0 || v != 0 {
+		t.Fatalf("Remaining = %d, %d", l, v)
+	}
+}
+
+func TestSleepStopsWhenContextDone(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	cancel()
+	if err := sleep(ctx, time.Hour); !errors.Is(err, context.Canceled) {
+		t.Fatalf("sleep err = %v", err)
+	}
+	if err := sleep(context.Background(), time.Millisecond); err != nil {
+		t.Fatalf("sleep err = %v", err)
+	}
+}