diff --git a/apps/backend/internal/orchestrator/event_handlers_agent.go b/apps/backend/internal/orchestrator/event_handlers_agent.go
index 8c614665d0..76b980790e 100644
--- a/apps/backend/internal/orchestrator/event_handlers_agent.go
+++ b/apps/backend/internal/orchestrator/event_handlers_agent.go
@@ -220,6 +220,15 @@ func (s *Service) executeQueuedMessage(callerSessionID string, queuedMsg *messag
 		return
 	}
 
+	attachments := make([]v1.MessageAttachment, len(queuedMsg.Attachments))
+	for i, att := range queuedMsg.Attachments {
+		attachments[i] = v1.MessageAttachment{
+			Type:     att.Type,
+			Data:     att.Data,
+			MimeType: att.MimeType,
+		}
+	}
+
 	// Create user message for the queued message (so it appears in chat history)
 	if s.messageCreator != nil {
 		turnID := s.getActiveTurnID(queuedMsg.SessionID)
@@ -229,9 +238,9 @@ func (s *Service) executeQueuedMessage(callerSessionID string, queuedMsg *messag
 			turnID = s.getActiveTurnID(queuedMsg.SessionID)
 		}
 
-		// Note: Attachments will be sent to the agent via PromptTask but not stored in the message
-		// This matches the behavior of direct prompts
-		meta := NewUserMessageMeta().WithPlanMode(queuedMsg.PlanMode)
+		meta := NewUserMessageMeta().
+			WithPlanMode(queuedMsg.PlanMode).
+			WithAttachments(attachments)
 		err := s.messageCreator.CreateUserMessage(promptCtx, queuedMsg.TaskID, queuedMsg.Content, queuedMsg.SessionID, turnID, meta.ToMap())
 		if err != nil {
 			s.logger.Error("failed to create user message for queued message",
@@ -248,16 +257,6 @@ func (s *Service) executeQueuedMessage(callerSessionID string, queuedMsg *messag
 		s.processOnTurnStartViaEngine(promptCtx, queuedMsg.TaskID, session)
 	}
 
-	// Convert queue attachments to v1 attachments
-	attachments := make([]v1.MessageAttachment, len(queuedMsg.Attachments))
-	for i, att := range queuedMsg.Attachments {
-		attachments[i] = v1.MessageAttachment{
-			Type:     att.Type,
-			Data:     att.Data,
-			MimeType: att.MimeType,
-		}
-	}
-
 	_, err := s.PromptTask(promptCtx, queuedMsg.TaskID, queuedMsg.SessionID,
 		queuedMsg.Content, queuedMsg.Model, queuedMsg.PlanMode, attachments)
 	if err != nil {
diff --git a/apps/backend/internal/orchestrator/event_handlers_queue_test.go b/apps/backend/internal/orchestrator/event_handlers_queue_test.go
index a176bc97a3..3318a0d61b 100644
--- a/apps/backend/internal/orchestrator/event_handlers_queue_test.go
+++ b/apps/backend/internal/orchestrator/event_handlers_queue_test.go
@@ -2,11 +2,13 @@ package orchestrator
 
 import (
 	"context"
+	"reflect"
 	"testing"
 
 	"github.com/kandev/kandev/internal/orchestrator/executor"
 	"github.com/kandev/kandev/internal/orchestrator/messagequeue"
 	"github.com/kandev/kandev/internal/task/models"
+	v1 "github.com/kandev/kandev/pkg/api/v1"
 )
 
 func TestExecuteQueuedMessage_RequeuesWhenResetInProgress(t *testing.T) {
@@ -47,3 +49,63 @@ func TestExecuteQueuedMessage_RequeuesWhenResetInProgress(t *testing.T) {
 		t.Fatalf("expected queued content to be preserved, got %q", status.Message.Content)
 	}
 }
+
+func TestExecuteQueuedMessage_StoresAttachmentsInUserMessageMetadata(t *testing.T) {
+	ctx := context.Background()
+	repo := setupTestRepo(t)
+	seedSession(t, repo, "t1", "s1", "step1")
+
+	session, err := repo.GetTaskSession(ctx, "s1")
+	if err != nil {
+		t.Fatalf("failed to get session: %v", err)
+	}
+	session.State = models.TaskSessionStateWaitingForInput
+	session.AgentExecutionID = "exec-1"
+	if err := repo.UpdateTaskSession(ctx, session); err != nil {
+		t.Fatalf("failed to update session: %v", err)
+	}
+
+	taskRepo := newMockTaskRepo()
+	agentMgr := &mockAgentManager{isAgentRunning: true}
+	svc := createTestServiceWithAgent(repo, newMockStepGetter(), taskRepo, agentMgr)
+	svc.executor = executor.NewExecutor(agentMgr, repo, testLogger(), executor.ExecutorConfig{})
+
+	mc := &mockMessageCreator{}
+	svc.messageCreator = mc
+
+	queuedAtts := []messagequeue.MessageAttachment{
+		{Type: "image", Data: "base64payload", MimeType: "image/png"},
+	}
+	queuedMsg := &messagequeue.QueuedMessage{
+		ID:          "q1",
+		SessionID:   "s1",
+		TaskID:      "t1",
+		Content:     "look at this screenshot",
+		Attachments: queuedAtts,
+		QueuedBy:    "test",
+	}
+
+	svc.executeQueuedMessage("s1", queuedMsg)
+
+	if len(mc.userMessages) != 1 {
+		t.Fatalf("expected 1 user message recorded, got %d", len(mc.userMessages))
+	}
+	meta := mc.userMessages[0].metadata
+	if meta == nil {
+		t.Fatalf("expected metadata on user message, got nil")
+	}
+	raw, ok := meta["attachments"]
+	if !ok {
+		t.Fatalf("expected metadata to contain 'attachments' key, got %v", meta)
+	}
+	got, ok := raw.([]v1.MessageAttachment)
+	if !ok {
+		t.Fatalf("expected attachments to be []v1.MessageAttachment, got %T", raw)
+	}
+	want := []v1.MessageAttachment{
+		{Type: "image", Data: "base64payload", MimeType: "image/png"},
+	}
+	if !reflect.DeepEqual(got, want) {
+		t.Fatalf("attachments mismatch\n got: %+v\nwant: %+v", got, want)
+	}
+}