diff --git a/pkg/agent/agent_media.go b/pkg/agent/agent_media.go
index 84f386f2d..1791a8510 100644
--- a/pkg/agent/agent_media.go
+++ b/pkg/agent/agent_media.go
@@ -21,25 +21,29 @@ import (
 )
 
 // resolveMediaRefs resolves media:// refs in messages.
-// Images are base64-encoded into the Media array for multimodal LLMs.
-// Non-image files (documents, audio, video) have their local path injected
-// into Content so the agent can access them via file tools like read_file.
+// 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).
+// 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 {
 	if store == nil {
 		return messages
 	}
 
-	result := make([]providers.Message, len(messages))
-	copy(result, messages)
+	result := make([]providers.Message, 0, len(messages))
 
-	for i, m := range result {
+	for _, m := range messages {
 		if len(m.Media) == 0 {
+			result = append(result, m)
 			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://") {
@@ -68,24 +72,78 @@ func resolveMediaRefs(messages []providers.Message, store media.MediaStore, maxS
 			mime := detectMIME(localPath, meta)
 			pathTags = append(pathTags, buildPathTag(mime, localPath))
 
-			if strings.HasPrefix(mime, "image/") {
+			// 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 != "" {
-					resolved = append(resolved, dataURL)
+					toolImageDataURLs = append(toolImageDataURLs, dataURL)
 				}
-				continue
 			}
 		}
 
-		result[i].Media = resolved
+		msg.Media = resolved
 		if len(pathTags) > 0 {
-			result[i].Content = injectPathTags(result[i].Content, pathTags)
+			msg.Content = injectPathTags(msg.Content, pathTags)
+		}
+		result = append(result, msg)
+
+		// Append a synthetic user message carrying the image data so the LLM
+		// can see it (tool messages don't support image_url in most APIs).
+		if len(toolImageDataURLs) > 0 {
+			result = append(result, providers.Message{
+				Role:  "user",
+				Content: "[Loaded image from tool result above]",
+				Media: toolImageDataURLs,
+			})
 		}
 	}
 
 	return result
 }
 
+// encodeImageToDataURL base64-encodes an image file into a data URL.
+// Returns empty string if the file exceeds maxSize or encoding fails.
+func encodeImageToDataURL(localPath, mime string, info os.FileInfo, maxSize int) string {
+	if info.Size() > int64(maxSize) {
+		logger.WarnCF("agent", "Media file too large, skipping", map[string]any{
+			"path":     localPath,
+			"size":     info.Size(),
+			"max_size": maxSize,
+		})
+		return ""
+	}
+
+	f, err := os.Open(localPath)
+	if err != nil {
+		logger.WarnCF("agent", "Failed to open media file", map[string]any{
+			"path":  localPath,
+			"error": err.Error(),
+		})
+		return ""
+	}
+	defer f.Close()
+
+	prefix := "data:" + mime + ";base64,"
+	encodedLen := base64.StdEncoding.EncodedLen(int(info.Size()))
+	var buf bytes.Buffer
+	buf.Grow(len(prefix) + encodedLen)
+	buf.WriteString(prefix)
+
+	encoder := base64.NewEncoder(base64.StdEncoding, &buf)
+	if _, err := io.Copy(encoder, f); err != nil {
+		logger.WarnCF("agent", "Failed to encode media file", map[string]any{
+			"path":  localPath,
+			"error": err.Error(),
+		})
+		return ""
+	}
+	encoder.Close()
+
+	return buf.String()
+}
+
 func buildArtifactTags(store media.MediaStore, refs []string) []string {
 	if store == nil || len(refs) == 0 {
 		return nil
@@ -136,49 +194,8 @@ func detectMIME(localPath string, meta media.MediaMeta) string {
 	return kind.MIME.Value
 }
 
-// encodeImageToDataURL base64-encodes an image file into a data URL.
-// Returns empty string if the file exceeds maxSize or encoding fails.
-func encodeImageToDataURL(localPath, mime string, info os.FileInfo, maxSize int) string {
-	if info.Size() > int64(maxSize) {
-		logger.WarnCF("agent", "Media file too large, skipping", map[string]any{
-			"path":     localPath,
-			"size":     info.Size(),
-			"max_size": maxSize,
-		})
-		return ""
-	}
-
-	f, err := os.Open(localPath)
-	if err != nil {
-		logger.WarnCF("agent", "Failed to open media file", map[string]any{
-			"path":  localPath,
-			"error": err.Error(),
-		})
-		return ""
-	}
-	defer f.Close()
-
-	prefix := "data:" + mime + ";base64,"
-	encodedLen := base64.StdEncoding.EncodedLen(int(info.Size()))
-	var buf bytes.Buffer
-	buf.Grow(len(prefix) + encodedLen)
-	buf.WriteString(prefix)
-
-	encoder := base64.NewEncoder(base64.StdEncoding, &buf)
-	if _, err := io.Copy(encoder, f); err != nil {
-		logger.WarnCF("agent", "Failed to encode media file", map[string]any{
-			"path":  localPath,
-			"error": err.Error(),
-		})
-		return ""
-	}
-	encoder.Close()
-
-	return buf.String()
-}
-
 // buildPathTag creates a structured tag exposing the local file path.
-// Tag type is derived from MIME: [audio:/path], [video:/path], or [file:/path].
+// Tag type is derived from MIME: [image:/path], [audio:/path], [video:/path], or [file:/path].
 func buildPathTag(mime, localPath string) string {
 	switch {
 	case strings.HasPrefix(mime, "image/"):
diff --git a/pkg/agent/agent_test.go b/pkg/agent/agent_test.go
index 14136aa38..e77eb0fac 100644
--- a/pkg/agent/agent_test.go
+++ b/pkg/agent/agent_test.go
@@ -4661,7 +4661,7 @@ func TestRun_PicoToolFeedbackSuppressesDuplicateInterimAssistantContent(t *testi
 	}
 }
 
-func TestResolveMediaRefs_ImageBase64AndPathTag(t *testing.T) {
+func TestResolveMediaRefs_ImageInjectsPathTag(t *testing.T) {
 	store := media.NewFileMediaStore()
 	dir := t.TempDir()
 
@@ -4689,11 +4689,8 @@ func TestResolveMediaRefs_ImageBase64AndPathTag(t *testing.T) {
 	}
 	result := resolveMediaRefs(messages, store, config.DefaultMaxMediaSize)
 
-	if len(result[0].Media) != 1 {
-		t.Fatalf("expected 1 resolved media, got %d", len(result[0].Media))
-	}
-	if !strings.HasPrefix(result[0].Media[0], "data:image/png;base64,") {
-		t.Fatalf("expected data:image/png;base64, prefix, got %q", result[0].Media[0][:40])
+	if len(result[0].Media) != 0 {
+		t.Fatalf("expected 0 media (images use path tags), got %d", len(result[0].Media))
 	}
 	localPath, _, _ := store.ResolveWithMeta(ref)
 	expectedContent := "describe this [image:" + localPath + "]"
@@ -4702,6 +4699,53 @@ func TestResolveMediaRefs_ImageBase64AndPathTag(t *testing.T) {
 	}
 }
 
+func TestResolveMediaRefs_ToolRoleImageAppendedAsUserMessage(t *testing.T) {
+	store := media.NewFileMediaStore()
+	dir := t.TempDir()
+
+	pngPath := filepath.Join(dir, "tool-result.png")
+	pngHeader := []byte{
+		0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A, // PNG signature
+		0x00, 0x00, 0x00, 0x0D, // IHDR length
+		0x49, 0x48, 0x44, 0x52, // "IHDR"
+		0x00, 0x00, 0x00, 0x01, 0x00, 0x00, 0x00, 0x01, 0x08, 0x02, // 1x1 RGB
+		0x00, 0x00, 0x00, // no interlace
+		0x90, 0x77, 0x53, 0xDE, // CRC
+	}
+	if err := os.WriteFile(pngPath, pngHeader, 0o644); err != nil {
+		t.Fatal(err)
+	}
+	ref, _ := store.Store(pngPath, media.MediaMeta{}, "test")
+
+	messages := []providers.Message{
+		{Role: "tool", Content: "Image loaded", Media: []string{ref}},
+	}
+	result := resolveMediaRefs(messages, store, config.DefaultMaxMediaSize)
+
+	// Tool message should have path tag but no base64
+	if len(result[0].Media) != 0 {
+		t.Fatalf("expected 0 media in tool message, got %d", len(result[0].Media))
+	}
+	localPath, _, _ := store.ResolveWithMeta(ref)
+	if !strings.Contains(result[0].Content, "[image:"+localPath+"]") {
+		t.Fatalf("expected image path tag in tool content, got %q", result[0].Content)
+	}
+
+	// A synthetic user message with base64 should follow
+	if len(result) != 2 {
+		t.Fatalf("expected 2 messages (tool + synthetic user), got %d", len(result))
+	}
+	if result[1].Role != "user" {
+		t.Fatalf("expected synthetic message role=user, got %q", result[1].Role)
+	}
+	if len(result[1].Media) != 1 {
+		t.Fatalf("expected 1 base64 media in synthetic user message, got %d", len(result[1].Media))
+	}
+	if !strings.HasPrefix(result[1].Media[0], "data:image/png;base64,") {
+		t.Fatalf("expected data:image/png;base64, prefix, got %q", result[1].Media[0][:40])
+	}
+}
+
 func TestResolveMediaRefs_OversizedImageSkipsBase64KeepsPathTag(t *testing.T) {
 	store := media.NewFileMediaStore()
 	dir := t.TempDir()
@@ -4806,11 +4850,8 @@ func TestResolveMediaRefs_UsesMetaContentType(t *testing.T) {
 	}
 	result := resolveMediaRefs(messages, store, config.DefaultMaxMediaSize)
 
-	if len(result[0].Media) != 1 {
-		t.Fatalf("expected 1 media, got %d", len(result[0].Media))
-	}
-	if !strings.HasPrefix(result[0].Media[0], "data:image/jpeg;base64,") {
-		t.Fatalf("expected jpeg prefix, got %q", result[0].Media[0][:30])
+	if len(result[0].Media) != 0 {
+		t.Fatalf("expected 0 media (images use path tags), got %d", len(result[0].Media))
 	}
 	localPath, _, _ := store.ResolveWithMeta(ref)
 	expectedContent := "hi [image:" + localPath + "]"
@@ -4948,11 +4989,8 @@ func TestResolveMediaRefs_MixedImageAndFile(t *testing.T) {
 	}
 	result := resolveMediaRefs(messages, store, config.DefaultMaxMediaSize)
 
-	if len(result[0].Media) != 1 {
-		t.Fatalf("expected 1 media (image base64 only), got %d", len(result[0].Media))
-	}
-	if !strings.HasPrefix(result[0].Media[0], "data:image/png;base64,") {
-		t.Fatal("expected image to be base64 encoded")
+	if len(result[0].Media) != 0 {
+		t.Fatalf("expected 0 media (all types use path tags), got %d", len(result[0].Media))
 	}
 	imgLocalPath, _, _ := store.ResolveWithMeta(imgRef)
 	pdfLocalPath, _, _ := store.ResolveWithMeta(fileRef)
diff --git a/pkg/agent/steering_test.go b/pkg/agent/steering_test.go
index 9330ec238..1ff699976 100644
--- a/pkg/agent/steering_test.go
+++ b/pkg/agent/steering_test.go
@@ -1051,18 +1051,16 @@ func TestAgentLoop_Continue_PreservesSteeringMedia(t *testing.T) {
 
 	foundResolvedMedia := false
 	for _, msg := range msgs {
-		if msg.Role != "user" {
+		if msg.Role != "user" || !strings.Contains(msg.Content, "describe this image") {
 			continue
 		}
-		hasBase64 := len(msg.Media) > 0 && strings.HasPrefix(msg.Media[0], "data:image/png;base64,")
-		hasPathTag := strings.Contains(msg.Content, "[image:")
-		if hasBase64 && hasPathTag {
+		if strings.Contains(msg.Content, "[image:") {
 			foundResolvedMedia = true
 			break
 		}
 	}
 	if !foundResolvedMedia {
-		t.Fatal("expected continue path to inject both base64 media and image path tag")
+		t.Fatal("expected continue path to inject image path tag into the provider request")
 	}
 
 	defaultAgent := al.registry.GetDefaultAgent()
diff --git a/pkg/tools/fs/load_image.go b/pkg/tools/fs/load_image.go
index 6f612faea..47022ed13 100644
--- a/pkg/tools/fs/load_image.go
+++ b/pkg/tools/fs/load_image.go
@@ -147,9 +147,9 @@ func (t *LoadImageTool) Execute(ctx context.Context, args map[string]any) *ToolR
 		return ErrorResult(fmt.Sprintf("failed to register image in media store: %v", err))
 	}
 
-	// Build the tool result text. The media:// ref will be picked up by
-	// resolveMediaRefs in loop_media.go and converted to a base64 data URL
-	// before the next LLM call, exactly like channel-received images.
+	// 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)
 
 	return &ToolResult{