fix(media): preserve tool-message ordering for multi-tool-call scenarios

Move synthetic user message (carrying base64 tool images) to after the
entire contiguous tool-message block instead of immediately after each
tool message. This preserves the assistant→tool→tool ordering required
by OpenAI-compatible APIs.

Also fix load_image to use generic [image: photo] placeholder so
injectPathTags can properly replace it with the actual path.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>

pkg/agent/agent_media.go

@@ -24,7 +24,8 @@ import (
 // For user messages: images get path tags only ([image:/path]) so the LLM
 // can decide whether to view them via load_image or operate on the file.
 // For tool messages: images are base64-encoded and appended as a synthetic
-// user message (many APIs don't support image_url in tool messages).
+// user message after the contiguous tool-message block ends, preserving
+// the required assistant→tool ordering for LLM APIs.
 // Non-image files always get path tags regardless of role.
 // Returns a new slice; original messages are not mutated.
 func resolveMediaRefs(messages []providers.Message, store media.MediaStore, maxSize int) []providers.Message {
@@ -33,17 +34,36 @@ func resolveMediaRefs(messages []providers.Message, store media.MediaStore, maxS
 	}
 
 	result := make([]providers.Message, 0, len(messages))
+	var pendingToolImages []string
+
+	for idx, m := range messages {
+		// When leaving a tool-message block, flush any accumulated images
+		// as a synthetic user message.
+		if m.Role != "tool" && len(pendingToolImages) > 0 {
+			result = append(result, providers.Message{
+				Role:    "user",
+				Content: "[Loaded image from tool result above]",
+				Media:   pendingToolImages,
+			})
+			pendingToolImages = nil
+		}
 
-	for _, m := range messages {
 		if len(m.Media) == 0 {
 			result = append(result, m)
+			if idx == len(messages)-1 && len(pendingToolImages) > 0 {
+				result = append(result, providers.Message{
+					Role:    "user",
+					Content: "[Loaded image from tool result above]",
+					Media:   pendingToolImages,
+				})
+				pendingToolImages = nil
+			}
 			continue
 		}
 
 		msg := m
 		resolved := make([]string, 0, len(m.Media))
 		var pathTags []string
-		var toolImageDataURLs []string
 
 		for _, ref := range m.Media {
 			if !strings.HasPrefix(ref, "media://") {
@@ -72,13 +92,10 @@ func resolveMediaRefs(messages []providers.Message, store media.MediaStore, maxS
 			mime := detectMIME(localPath, meta)
 			pathTags = append(pathTags, buildPathTag(mime, localPath))
 
-			// For tool results (e.g. load_image), base64-encode images into a
-			// separate user message — many LLM APIs don't support image_url in
-			// tool messages.
 			if m.Role == "tool" && strings.HasPrefix(mime, "image/") {
 				dataURL := encodeImageToDataURL(localPath, mime, info, maxSize)
 				if dataURL != "" {
-					toolImageDataURLs = append(toolImageDataURLs, dataURL)
+					pendingToolImages = append(pendingToolImages, dataURL)
 				}
 			}
 		}
@@ -89,14 +106,14 @@ func resolveMediaRefs(messages []providers.Message, store media.MediaStore, maxS
 		}
 		result = append(result, msg)
 
-		// Append a synthetic user message carrying the image data so the LLM
+		// If this is the last message and we have pending images, flush them.
-		// can see it (tool messages don't support image_url in most APIs).
+		if idx == len(messages)-1 && len(pendingToolImages) > 0 {
-		if len(toolImageDataURLs) > 0 {
 			result = append(result, providers.Message{
 				Role:    "user",
 				Content: "[Loaded image from tool result above]",
-				Media: toolImageDataURLs,
+				Media:   pendingToolImages,
 			})
+			pendingToolImages = nil
 		}
 	}
 

pkg/agent/agent_test.go

@@ -4746,6 +4746,52 @@ func TestResolveMediaRefs_ToolRoleImageAppendedAsUserMessage(t *testing.T) {
 	}
 }
 
+func TestResolveMediaRefs_MultiToolCallPreservesOrdering(t *testing.T) {
+	store := media.NewFileMediaStore()
+	dir := t.TempDir()
+
+	// Create image for tool #1
+	pngPath := filepath.Join(dir, "loaded.png")
+	pngHeader := []byte{
+		0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A, // PNG signature
+		0x00, 0x00, 0x00, 0x0D, 0x49, 0x48, 0x44, 0x52, // IHDR
+		0x00, 0x00, 0x00, 0x01, 0x00, 0x00, 0x00, 0x01, 0x08, 0x02,
+		0x00, 0x00, 0x00, 0x90, 0x77, 0x53, 0xDE,
+	}
+	os.WriteFile(pngPath, pngHeader, 0o644)
+	imgRef, _ := store.Store(pngPath, media.MediaMeta{}, "test")
+
+	// Simulate: assistant called load_image + read_file, two tool results follow
+	messages := []providers.Message{
+		{Role: "assistant", Content: "Let me load the image and read the file."},
+		{Role: "tool", Content: "Image loaded [image: photo]", Media: []string{imgRef}},
+		{Role: "tool", Content: "file contents here"},
+	}
+	result := resolveMediaRefs(messages, store, config.DefaultMaxMediaSize)
+
+	// assistant, tool#1, tool#2 must remain contiguous — no user in between
+	if result[0].Role != "assistant" {
+		t.Fatalf("result[0] expected assistant, got %q", result[0].Role)
+	}
+	if result[1].Role != "tool" {
+		t.Fatalf("result[1] expected tool, got %q", result[1].Role)
+	}
+	if result[2].Role != "tool" {
+		t.Fatalf("result[2] expected tool, got %q", result[2].Role)
+	}
+
+	// Synthetic user message should come AFTER the tool block
+	if len(result) != 4 {
+		t.Fatalf("expected 4 messages (assistant + 2 tool + synthetic user), got %d", len(result))
+	}
+	if result[3].Role != "user" {
+		t.Fatalf("result[3] expected user, got %q", result[3].Role)
+	}
+	if len(result[3].Media) != 1 || !strings.HasPrefix(result[3].Media[0], "data:image/png;base64,") {
+		t.Fatal("expected synthetic user message to contain base64 image")
+	}
+}
+
 func TestResolveMediaRefs_OversizedImageSkipsBase64KeepsPathTag(t *testing.T) {
 	store := media.NewFileMediaStore()
 	dir := t.TempDir()

pkg/tools/fs/load_image.go

@@ -150,7 +150,7 @@ func (t *LoadImageTool) Execute(ctx context.Context, args map[string]any) *ToolR
 	// Build the tool result text. The media:// ref in Media will be picked
 	// up by resolveMediaRefs in agent_media.go and base64-encoded for tool
 	// result messages (role="tool"), so the LLM can see the image content.
-	msg := fmt.Sprintf("Image loaded: %s\n[image: %s]", filename, ref)
+	msg := fmt.Sprintf("Image loaded: %s\n[image: photo]", filename)
 
 	return &ToolResult{
 		ForLLM:  msg,