diff --git a/frontend/src/app/api/[...path]/route.ts b/frontend/src/app/api/[...path]/route.ts
index 97dae30..cb09b15 100644
--- a/frontend/src/app/api/[...path]/route.ts
+++ b/frontend/src/app/api/[...path]/route.ts
@@ -1,7 +1,7 @@
 import type { NextRequest } from "next/server";
 
 export const dynamic = "force-dynamic";
-export const maxDuration = 120;
+export const maxDuration = 1200;
 export const runtime = "nodejs";
 
 const apiBase = () => process.env.NEXT_PUBLIC_API_PROXY ?? "http://localhost:8888";
diff --git a/server/internal/config/config.go b/server/internal/config/config.go
index 3929889..f10edc3 100644
--- a/server/internal/config/config.go
+++ b/server/internal/config/config.go
@@ -123,11 +123,12 @@ type AgentConfig struct {
 }
 
 type ImageGenerationConfig struct {
-	BaseURL             string `json:",optional"`
-	APIKey              string `json:",optional"`
-	APIKeyEnv           string `json:",default=GPT_IMAGE_API_KEY"`
-	InputImageTransport string `json:",default=file"`
-	TimeoutSeconds      int    `json:",default=600"`
+	BaseURL                      string `json:",optional"`
+	APIKey                       string `json:",optional"`
+	APIKeyEnv                    string `json:",default=GPT_IMAGE_API_KEY"`
+	InputImageTransport          string `json:",default=file"`
+	TimeoutSeconds               int    `json:",default=600"`
+	ResponseHeaderTimeoutSeconds int    `json:",default=240"`
 }
 
 type TextExtractionConfig struct {
diff --git a/server/internal/infrastructure/piagent/image_generation.go b/server/internal/infrastructure/piagent/image_generation.go
index 1ee3171..c4e6373 100644
--- a/server/internal/infrastructure/piagent/image_generation.go
+++ b/server/internal/infrastructure/piagent/image_generation.go
@@ -25,8 +25,9 @@ import (
 )
 
 const (
-	defaultImageGenerationTimeout = 10 * time.Minute
-	maxImageGenerationTimeout     = 10 * time.Minute
+	defaultImageGenerationTimeout               = 10 * time.Minute
+	defaultImageGenerationResponseHeaderTimeout = 4 * time.Minute
+	maxImageGenerationTimeout                   = 10 * time.Minute
 )
 
 type ImageGenerator interface {
@@ -47,10 +48,11 @@ type ImageRequestOptions struct {
 }
 
 type ImageClientOptions struct {
-	BaseURL             string
-	APIKey              string
-	InputImageTransport string
-	TimeoutSeconds      int
+	BaseURL                      string
+	APIKey                       string
+	InputImageTransport          string
+	TimeoutSeconds               int
+	ResponseHeaderTimeoutSeconds int
 }
 
 type ImageClient struct {
@@ -71,6 +73,13 @@ func NewImageClient(opts ImageClientOptions) *ImageClient {
 	if timeout > maxImageGenerationTimeout {
 		timeout = maxImageGenerationTimeout
 	}
+	responseHeaderTimeout := time.Duration(opts.ResponseHeaderTimeoutSeconds) * time.Second
+	if responseHeaderTimeout <= 0 {
+		responseHeaderTimeout = defaultImageGenerationResponseHeaderTimeout
+	}
+	if responseHeaderTimeout > timeout {
+		responseHeaderTimeout = timeout
+	}
 
 	return &ImageClient{
 		baseURL:             strings.TrimRight(opts.BaseURL, "/"),
@@ -83,6 +92,7 @@ func NewImageClient(opts ImageClientOptions) *ImageClient {
 				DialContext:           (&net.Dialer{Timeout: 30 * time.Second, KeepAlive: 30 * time.Second}).DialContext,
 				DisableKeepAlives:     true,
 				ForceAttemptHTTP2:     false,
+				ResponseHeaderTimeout: responseHeaderTimeout,
 				TLSHandshakeTimeout:   10 * time.Second,
 				ExpectContinueTimeout: time.Second,
 			},
@@ -147,9 +157,13 @@ func (c *ImageClient) Generate(ctx context.Context, prompt string, opts ImageReq
 			)
 			return image, nil
 		}
+		if ctx.Err() != nil {
+			return GeneratedImage{}, ctx.Err()
+		}
 		lastErr = err
-		retryable := isRetryableImageGenerationError(err)
-		terminal := isImageGenerationTerminalError(err)
+		timeoutRetryable := idempotencyKey != "" && isImageGenerationTimeoutError(err)
+		retryable := isRetryableImageGenerationError(err) || timeoutRetryable
+		terminal := isImageGenerationTerminalError(err) && !timeoutRetryable
 		logx.Errorf(
 			"gpt image generation failed model=%s size=%s count=%d prompt_runes=%d attempt=%d elapsed=%s timeout=%s retryable=%t terminal=%t idempotency_key=%s err=%v",
 			model,
@@ -537,6 +551,13 @@ func isImageGenerationTerminalError(err error) bool {
 	if errors.Is(err, context.Canceled) || errors.Is(err, context.DeadlineExceeded) {
 		return true
 	}
+	return isImageGenerationTimeoutError(err)
+}
+
+func isImageGenerationTimeoutError(err error) bool {
+	if err == nil {
+		return false
+	}
 	var netErr net.Error
 	if errors.As(err, &netErr) && netErr.Timeout() {
 		return true
diff --git a/server/internal/infrastructure/piagent/image_generation_test.go b/server/internal/infrastructure/piagent/image_generation_test.go
index 17c5cb3..bd40e5f 100644
--- a/server/internal/infrastructure/piagent/image_generation_test.go
+++ b/server/internal/infrastructure/piagent/image_generation_test.go
@@ -347,3 +347,41 @@ func TestImageClientDoesNotRetryRequestTimeout(t *testing.T) {
 		t.Fatalf("expected timeout to fail fast without retry, got %d calls", calls)
 	}
 }
+
+func TestImageClientRetriesIdempotentResponseHeaderTimeout(t *testing.T) {
+	calls := 0
+	var keys []string
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		calls++
+		keys = append(keys, r.Header.Get("Idempotency-Key"))
+		if calls == 1 {
+			time.Sleep(80 * time.Millisecond)
+			return
+		}
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"data":[{"url":"https://example.com/recovered.png"}]}`))
+	}))
+	defer server.Close()
+
+	client := NewImageClient(ImageClientOptions{BaseURL: server.URL, APIKey: "test-key"})
+	transport, ok := client.client.Transport.(*http.Transport)
+	if !ok {
+		t.Fatalf("expected http transport, got %T", client.client.Transport)
+	}
+	transport.ResponseHeaderTimeout = 20 * time.Millisecond
+	client.client.Timeout = time.Second
+
+	image, err := client.Generate(context.Background(), "create an image", ImageRequestOptions{Model: "gpt-image-2", IdempotencyKey: "same-generation"})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if image.URL != "https://example.com/recovered.png" {
+		t.Fatalf("expected recovered image, got %#v", image)
+	}
+	if calls != 2 {
+		t.Fatalf("expected one retry after timeout, got %d calls", calls)
+	}
+	if len(keys) != 2 || keys[0] != "same-generation" || keys[1] != "same-generation" {
+		t.Fatalf("expected retry to keep idempotency key, got %#v", keys)
+	}
+}
diff --git a/server/internal/svc/service_context.go b/server/internal/svc/service_context.go
index abeb74e..ae53b5b 100644
--- a/server/internal/svc/service_context.go
+++ b/server/internal/svc/service_context.go
@@ -305,10 +305,11 @@ func newImageGenerator(c config.Config) piagent.ImageGenerator {
 	opts := c.Agent.Image
 	apiKey := resolveImageAPIKey(opts)
 	client := piagent.NewImageClient(piagent.ImageClientOptions{
-		BaseURL:             opts.BaseURL,
-		APIKey:              apiKey,
-		InputImageTransport: opts.InputImageTransport,
-		TimeoutSeconds:      opts.TimeoutSeconds,
+		BaseURL:                      opts.BaseURL,
+		APIKey:                       apiKey,
+		InputImageTransport:          opts.InputImageTransport,
+		TimeoutSeconds:               opts.TimeoutSeconds,
+		ResponseHeaderTimeoutSeconds: opts.ResponseHeaderTimeoutSeconds,
 	})
 	if client == nil {
 		return nil