diff --git a/api.go b/api.go
index 6c9fc05..4058f4a 100644
--- a/api.go
+++ b/api.go
@@ -120,8 +120,12 @@ func (e *Engine) Serve(ctx context.Context) error {
 		close(errCh)
 	}()
 
-	// Block until context is cancelled.
-	<-ctx.Done()
+	// Return immediately if the listener fails before shutdown is requested.
+	select {
+	case err := <-errCh:
+		return err
+	case <-ctx.Done():
+	}
 
 	// Signal SSE clients first so their handlers can exit cleanly before the
 	// HTTP server begins its own shutdown sequence.
diff --git a/api_test.go b/api_test.go
index f4bd8b5..3198c8c 100644
--- a/api_test.go
+++ b/api_test.go
@@ -202,3 +202,32 @@ func TestServe_Good_GracefulShutdown(t *testing.T) {
 		t.Fatal("Serve did not return within 5 seconds after context cancellation")
 	}
 }
+
+func TestServe_Bad_ReturnsListenErrorBeforeCancel(t *testing.T) {
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("failed to reserve port: %v", err)
+	}
+	addr := ln.Addr().String()
+	defer ln.Close()
+
+	e, _ := api.New(api.WithAddr(addr))
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	errCh := make(chan error, 1)
+	go func() {
+		errCh <- e.Serve(ctx)
+	}()
+
+	select {
+	case serveErr := <-errCh:
+		if serveErr == nil {
+			t.Fatal("expected Serve to return a listen error, got nil")
+		}
+	case <-time.After(2 * time.Second):
+		cancel()
+		t.Fatal("Serve did not return promptly after listener failure")
+	}
+}