diff --git a/try.go b/try.go
index 8f6c91a..a2c0ba1 100644
--- a/try.go
+++ b/try.go
@@ -356,7 +356,8 @@ func shouldRetry(ctx context.Context, cfg *Config, err error) bool {
 
 func calculateNextDelay(cfg *Config, attempt int, err error) time.Duration {
 	// 1. Check for Retry-After override — takes precedence over everything.
-	if ra, ok := err.(RetryAfterer); ok {
+	var ra RetryAfterer
+	if errors.As(err, &ra) {
 		d := ra.RetryAfter()
 		if d > cfg.MaxDelay {
 			return cfg.MaxDelay
diff --git a/try_test.go b/try_test.go
index bbd0517..66a5fc5 100644
--- a/try_test.go
+++ b/try_test.go
@@ -101,6 +101,13 @@ type retryAfterError struct{ d time.Duration }
 func (e retryAfterError) Error() string             { return "retry after" }
 func (e retryAfterError) RetryAfter() time.Duration { return e.d }
 
+type wrappedRetryAfterError struct {
+	retryAfterError
+	err error
+}
+
+func (e wrappedRetryAfterError) Unwrap() error { return e.err }
+
 func TestDo_RetryAfter(t *testing.T) {
 	ctx := context.Background()
 	clk := &testClock{afterChan: make(chan time.Time)}
@@ -126,6 +133,65 @@ func TestDo_RetryAfter(t *testing.T) {
 	}
 }
 
+func TestDo_RetryAfterWrapped(t *testing.T) {
+	const requestedDelay = 20 * time.Millisecond
+	const maxDelay = 50 * time.Millisecond
+	const fallbackDelay = time.Millisecond
+	raErr := retryAfterError{d: requestedDelay}
+	cappedErr := retryAfterError{d: time.Hour}
+	unrelatedErr := errors.New("unrelated failure")
+
+	tests := []struct {
+		name string
+		err  error
+		want time.Duration
+	}{
+		{"direct", raErr, requestedDelay},
+		{"outer retry after", wrappedRetryAfterError{retryAfterError{d: maxDelay}, raErr}, maxDelay},
+		{"wrapped", fmt.Errorf("request failed: %w", raErr), requestedDelay},
+		{"nested", fmt.Errorf("operation failed: %w", fmt.Errorf("request failed: %w", raErr)), requestedDelay},
+		{"joined", errors.Join(unrelatedErr, raErr), requestedDelay},
+		{"wrapped capped", fmt.Errorf("request failed: %w", cappedErr), maxDelay},
+		{"joined capped", errors.Join(unrelatedErr, cappedErr), maxDelay},
+		{"no retry after", fmt.Errorf("request failed: %w", unrelatedErr), fallbackDelay},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			clk := &testClock{afterChan: make(chan time.Time, 1)}
+			clk.afterChan <- time.Now()
+			var observedDelay time.Duration
+			calls := 0
+			fallbackCalls := 0
+			val, err := Do(context.Background(), func(context.Context) (string, error) {
+				calls++
+				if calls == 1 {
+					return "", tt.err
+				}
+				return "ok", nil
+			}, WithAttempts(2), WithClock(clk), WithMaxDelay(maxDelay),
+				WithDelayFunc(func(int, error) time.Duration {
+					fallbackCalls++
+					return fallbackDelay
+				}),
+				WithOnRetry(func(info RetryInfo) { observedDelay = info.Delay }),
+			)
+			if err != nil || val != "ok" || calls != 2 {
+				t.Fatalf("Do returned (%q, %v) after %d calls", val, err, calls)
+			}
+			if observedDelay != tt.want {
+				t.Errorf("retry delay = %v, want %v", observedDelay, tt.want)
+			}
+			wantFallbackCalls := 0
+			if tt.want == fallbackDelay {
+				wantFallbackCalls = 1
+			}
+			if fallbackCalls != wantFallbackCalls {
+				t.Errorf("delay function called %d times, want %d", fallbackCalls, wantFallbackCalls)
+			}
+		})
+	}
+}
+
 func TestDo_Generics(t *testing.T) {
 	ctx := context.Background()