diff --git a/internal/ai/llm/retry.go b/internal/ai/llm/retry.go
new file mode 100644
index 0000000..72eb534
--- /dev/null
+++ b/internal/ai/llm/retry.go
@@ -0,0 +1,107 @@
+package llm
+
+import (
+	"context"
+	"errors"
+	"math/rand/v2"
+	"time"
+)
+
+const (
+	// DefaultTimeout bounds each Generate attempt 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, 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. A retry whose wait would not end before the
+// caller's context 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.
+// A req.Timeout of 0 becomes DefaultTimeout; either bounds each attempt,
+// not the whole call, which ctx bounds.
+func (r *Retrying) Generate(ctx context.Context, req Request) (Response, error) {
+	if req.Timeout == 0 {
+		req.Timeout = DefaultTimeout
+	}
+	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 deadline, has := ctx.Deadline(); has && !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 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()
+	}
+}
diff --git a/internal/ai/llm/retry_test.go b/internal/ai/llm/retry_test.go
new file mode 100644
index 0000000..6000f9a
--- /dev/null
+++ b/internal/ai/llm/retry_test.go
@@ -0,0 +1,271 @@
+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{MaxRetryAfter}; !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"), ""),
+		"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)
+		})
+	}
+}
+
+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)
+}
+
+func TestRetryingDefaultTimeout(t *testing.T) {
+	r, f, _ := newTestRetrying()
+	f.QueueGenerate(ok("a"), ok("b"))
+	custom := retryReq
+	custom.Timeout = 5 * time.Second
+
+	for _, req := range []Request{retryReq, custom} {
+		if _, err := r.Generate(context.Background(), req); err != nil {
+			t.Fatal(err)
+		}
+	}
+	got := f.Requests()
+	if got[0].Timeout != DefaultTimeout || got[1].Timeout != 5*time.Second {
+		t.Fatalf("timeouts = %v, %v; want %v, 5s", got[0].Timeout, got[1].Timeout, DefaultTimeout)
+	}
+}
+
+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)
+	}
+}