fix(agent): deduplicate automatic media delivery

internal/agent/loop_context.go

@@ -403,8 +403,8 @@ func (l *Loop) injectContext(ctx context.Context, req *RunRequest) (contextSetup
 	// Inject agent key into context for tool-level resolution (multiple agents share tool registry)
 	ctx = tools.WithToolAgentKey(ctx, l.id)
 
-	// Inject delivered media tracker so write_file and message tool can coordinate:
-	// write_file(deliver=true) marks paths, message self-send guard checks before allowing.
+	// Inject delivered media tracker so automatic output collection and direct
+	// media sends can coordinate within this run.
 	ctx = tools.WithDeliveredMedia(ctx, tools.NewDeliveredMedia())
 
 	// Security: truncate oversized user messages gracefully (feed truncation notice into LLM)

internal/agent/loop_media_delivery_dedup_test.go

@@ -0,0 +1,122 @@
+package agent
+
+import (
+	"context"
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/nextlevelbuilder/goclaw/internal/bus"
+	"github.com/nextlevelbuilder/goclaw/internal/providers"
+	"github.com/nextlevelbuilder/goclaw/internal/tools"
+)
+
+func TestProcessToolResultBlocksMessageSelfSendForQueuedMedia(t *testing.T) {
+	workspace := t.TempDir()
+	workspace, err := filepath.EvalSymlinks(workspace)
+	if err != nil {
+		t.Fatal(err)
+	}
+	mediaPath := filepath.Join(workspace, "generated-image.png")
+	if err := os.WriteFile(mediaPath, []byte("image"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+
+	delivered := tools.NewDeliveredMedia()
+	ctx := context.Background()
+	ctx = tools.WithToolWorkspace(ctx, workspace)
+	ctx = tools.WithToolChannel(ctx, "lark-test")
+	ctx = tools.WithToolChatID(ctx, "chat-1")
+	ctx = tools.WithDeliveredMedia(ctx, delivered)
+
+	loop := &Loop{id: "test-agent"}
+	state := &runState{}
+	loop.processToolResult(
+		ctx,
+		state,
+		&RunRequest{RunID: "run-1"},
+		func(AgentEvent) {},
+		providers.ToolCall{ID: "create-1", Name: "create_image"},
+		"create_image",
+		&tools.Result{
+			ForLLM: "MEDIA:" + mediaPath,
+			Media: []bus.MediaFile{{
+				Path:     mediaPath,
+				MimeType: "image/png",
+			}},
+		},
+		false,
+	)
+
+	if len(state.mediaResults) != 1 {
+		t.Fatalf("queued media = %d, want 1", len(state.mediaResults))
+	}
+
+	messageTool := tools.NewMessageTool(workspace, true)
+	messageTool.SetMessageBus(bus.New())
+	result := messageTool.Execute(ctx, map[string]any{
+		"action":  "send",
+		"channel": "lark-test",
+		"target":  "chat-1",
+		"message": "MEDIA:" + mediaPath,
+	})
+	if !result.IsError {
+		t.Fatal("message self-send succeeded for media already queued by the agent loop")
+	}
+	if !strings.Contains(result.ForLLM, "already queued for automatic delivery") {
+		t.Fatalf("message self-send blocked for the wrong reason: %q", result.ForLLM)
+	}
+
+	otherPath := filepath.Join(workspace, "manual-attachment.txt")
+	if err := os.WriteFile(otherPath, []byte("attachment"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+	result = messageTool.Execute(ctx, map[string]any{
+		"action":  "send",
+		"channel": "lark-test",
+		"target":  "chat-1",
+		"message": "Attachments:\nMEDIA:" + mediaPath + "\nMEDIA:" + otherPath,
+	})
+	if !result.IsError {
+		t.Fatal("mixed message self-send included media already queued by the agent loop")
+	}
+	if !strings.Contains(result.ForLLM, "already queued for automatic delivery") {
+		t.Fatalf("mixed message self-send blocked for the wrong reason: %q", result.ForLLM)
+	}
+}
+
+func TestProcessToolResultMarksLegacyMediaAsQueued(t *testing.T) {
+	workspace := t.TempDir()
+	workspace, err := filepath.EvalSymlinks(workspace)
+	if err != nil {
+		t.Fatal(err)
+	}
+	mediaPath := filepath.Join(workspace, "legacy-output.pdf")
+	if err := os.WriteFile(mediaPath, []byte("pdf"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+
+	delivered := tools.NewDeliveredMedia()
+	ctx := tools.WithToolWorkspace(context.Background(), workspace)
+	ctx = tools.WithDeliveredMedia(ctx, delivered)
+
+	state := &runState{}
+	(&Loop{id: "test-agent"}).processToolResult(
+		ctx,
+		state,
+		&RunRequest{RunID: "run-legacy"},
+		func(AgentEvent) {},
+		providers.ToolCall{ID: "exec-1", Name: "exec"},
+		"exec",
+		&tools.Result{ForLLM: "MEDIA:" + mediaPath},
+		false,
+	)
+
+	if len(state.mediaResults) != 1 {
+		t.Fatalf("queued legacy media = %d, want 1", len(state.mediaResults))
+	}
+	if !delivered.IsDelivered(mediaPath) {
+		t.Fatalf("legacy media %q was not marked for automatic delivery", mediaPath)
+	}
+}

internal/agent/loop_tools.go

@@ -118,6 +118,12 @@ func (l *Loop) processToolResult(
 				mr.Prompt = result.MediaPrompts[i]
 			}
 			rs.mediaResults = append(rs.mediaResults, mr)
+			// The file is now queued for the run's automatic outbound delivery.
+			// Mark it so a later message(MEDIA:same_path) self-send cannot publish
+			// the same attachment before the final response is dispatched.
+			if dm := tools.DeliveredMediaFromCtx(ctx); dm != nil {
+				dm.Mark(cleaned)
+			}
 		}
 	} else if mr := parseMediaResult(result.ForLLM); mr != nil {
 		// Security (egress boundary): a tool's MEDIA:<path> output is taken
@@ -129,6 +135,9 @@ func (l *Loop) processToolResult(
 		if cleaned, ok := confineToAnyRoot(mr.Path, mediaRoots); ok {
 			mr.Path = cleaned
 			rs.mediaResults = append(rs.mediaResults, *mr)
+			if dm := tools.DeliveredMediaFromCtx(ctx); dm != nil {
+				dm.Mark(cleaned)
+			}
 		} else {
 			slog.Warn("security.media_path_rejected",
 				"agent", l.id, "tool", tc.Name, "path", mr.Path,

internal/tools/context_keys.go

@@ -774,12 +774,12 @@ func WorkstationIDFromCtx(ctx context.Context) string {
 	return v
 }
 
-// --- Delivered media tracker (write_file → message self-send dedup) ---
+// --- Delivered media tracker (automatic delivery → direct-send dedup) ---
 
 const ctxDeliveredMedia toolContextKey = "tool_delivered_media"
 
-// DeliveredMedia tracks file paths already queued for auto-delivery by write_file.
-// Injected once per run via WithDeliveredMedia; write_file marks paths, message reads them.
+// DeliveredMedia tracks file paths already queued or sent during an agent run.
+// Automatic media producers mark paths, and direct-send tools consult the tracker.
 // Thread-safe: tools may execute in parallel goroutines.
 type DeliveredMedia struct {
 	mu    sync.Mutex

internal/tools/message.go

@@ -141,9 +141,8 @@ func (t *MessageTool) Execute(ctx context.Context, args map[string]any) *Result
 	// Self-send guard: prevent agent from sending to its own chat via message tool.
 	// Text self-sends are always blocked (response goes through normal outbound).
 	// MEDIA self-sends are allowed ONLY when the file was NOT already queued for
-	// delivery (i.e. write_file was called with deliver=false). This prevents both
-	// duplicate delivery (deliver=true then message MEDIA:) and runaway retry loops
-	// (deliver=false then message MEDIA: blocked unconditionally).
+	// automatic delivery. This prevents both duplicate delivery and runaway retry
+	// loops while preserving explicit delivery of files that are not auto-queued.
 	ctxChannel := ToolChannelFromCtx(ctx)
 	ctxChatID := ToolChatIDFromCtx(ctx)
 	isSelfSend := ctxChannel != "" && ctxChatID != "" && channel == ctxChannel && target == ctxChatID
@@ -152,21 +151,22 @@ func (t *MessageTool) Execute(ctx context.Context, args map[string]any) *Result
 		if !isMediaSend {
 			return ErrorResult("You are already responding to this chat. Your response text will be delivered automatically. Do not use the message tool to send text to your own chat — just include the content in your response text. To deliver files, use write_file with deliver=true instead.")
 		}
-		// MEDIA self-send: block if ALL referenced files are already queued for delivery.
-		// Extracts paths from both standalone "MEDIA:path" and embedded multi-line messages.
+		// MEDIA self-send: block if any referenced file is already queued for
+		// delivery. Sending a mixed set would still duplicate the queued files;
+		// the model can retry with only the undelivered references.
 		if dm := DeliveredMediaFromCtx(ctx); dm != nil {
 			mediaRefs := embeddedMediaPattern.FindAllString(message, -1)
-			allDelivered := len(mediaRefs) > 0
+			hasDelivered := false
 			for _, raw := range mediaRefs {
 				if filePath, ok := t.resolveMediaPath(ctx, raw); ok {
-					if !dm.IsDelivered(filePath) {
-						allDelivered = false
+					if dm.IsDelivered(filePath) {
+						hasDelivered = true
 						break
 					}
 				}
 			}
-			if allDelivered {
-				return ErrorResult("This file is already queued for automatic delivery via write_file(deliver=true). Do not send it again. To deliver files that were written with deliver=false, use write_file again with deliver=true, or use message(MEDIA:path) which is allowed for undelivered files.")
+			if hasDelivered {
+				return ErrorResult("One or more files are already queued for automatic delivery. Do not send them again with message(MEDIA:path). Retry with only files that are not queued for automatic delivery.")
 			}
 		}
 	}