diff --git a/apps/backend/internal/orchestrator/event_handlers_workflow.go b/apps/backend/internal/orchestrator/event_handlers_workflow.go
index be663c0061..5136eed9be 100644
--- a/apps/backend/internal/orchestrator/event_handlers_workflow.go
+++ b/apps/backend/internal/orchestrator/event_handlers_workflow.go
@@ -568,7 +568,13 @@ func (s *Service) reuseSessionForStep(ctx context.Context, taskID string, curren
 	// and gets delivered to the wrong agent the next time that previous
 	// session is reused (e.g. on the on_turn_complete bounce back).
 	if s.messageQueue != nil {
-		s.messageQueue.TransferSession(ctx, currentSession.ID, existing.ID)
+		if err := s.messageQueue.TransferSession(ctx, currentSession.ID, existing.ID); err != nil {
+			// Fail closed: the workflow switch reuses an existing session, but
+			// orphaning a queued hand-off prompt on the previous session would
+			// silently misroute the next prompt. Stop here and surface the
+			// error so the caller can decide whether to retry.
+			return nil, fmt.Errorf("transfer queued state to reused session: %w", err)
+		}
 	}
 
 	s.completeAndStopSession(ctx, taskID, currentSession)
@@ -650,7 +656,17 @@ func (s *Service) createNewSessionForStep(ctx context.Context, taskID string, cu
 	// pending move from the old session to the new one — the queue is keyed by
 	// session ID, and without this the prompt would never reach the new agent.
 	if s.messageQueue != nil {
-		s.messageQueue.TransferSession(ctx, currentSession.ID, newSession.ID)
+		if err := s.messageQueue.TransferSession(ctx, currentSession.ID, newSession.ID); err != nil {
+			s.logger.Error("transfer queue to new session failed; queued prompts on the previous session will not be drained",
+				zap.String("from_session_id", currentSession.ID),
+				zap.String("to_session_id", newSession.ID),
+				zap.Error(err))
+			// Continue anyway: the new session is already created and committed
+			// upstream. Failing closed here would leave the workflow in a
+			// half-switched state (new session exists but caller thinks it
+			// failed). The error is surfaced via logs and the orphaned entries
+			// stay safely in the old session for manual recovery.
+		}
 	}
 
 	// Promote the new session to primary so it's loaded when navigating back to this task.
diff --git a/apps/backend/internal/orchestrator/messagequeue/service.go b/apps/backend/internal/orchestrator/messagequeue/service.go
index bbd185d1e1..4dfbc994ee 100644
--- a/apps/backend/internal/orchestrator/messagequeue/service.go
+++ b/apps/backend/internal/orchestrator/messagequeue/service.go
@@ -176,19 +176,22 @@ func (s *Service) GetStatus(ctx context.Context, sessionID string) *QueueStatus
 }
 
 // TransferSession moves any queued messages and pending move from one session
-// to another. Used by workflow session switches (when a target step has a
-// different agent profile and switchSessionForStep creates a new session).
-func (s *Service) TransferSession(ctx context.Context, oldSessionID, newSessionID string) {
+// to another. Used by workflow session switches. Returns an error so the
+// caller can fail closed instead of silently leaving entries orphaned on the
+// old session — a transfer that no-ops without a signal would let the workflow
+// step move forward while the queue sticks behind.
+func (s *Service) TransferSession(ctx context.Context, oldSessionID, newSessionID string) error {
 	if err := s.repo.TransferSession(ctx, oldSessionID, newSessionID); err != nil {
 		s.logger.Error("transfer session failed",
 			zap.String("from_session_id", oldSessionID),
 			zap.String("to_session_id", newSessionID),
 			zap.Error(err))
-		return
+		return err
 	}
 	s.logger.Info("transferred queue between sessions",
 		zap.String("from_session_id", oldSessionID),
 		zap.String("to_session_id", newSessionID))
+	return nil
 }
 
 // SetPendingMove records a pending move for a session (replaces any existing one).
diff --git a/apps/web/lib/api/domains/queue-api.test.ts b/apps/web/lib/api/domains/queue-api.test.ts
index d11bff394c..aa4ec28b7a 100644
--- a/apps/web/lib/api/domains/queue-api.test.ts
+++ b/apps/web/lib/api/domains/queue-api.test.ts
@@ -11,6 +11,7 @@ describe("rethrowQueueError", () => {
       }),
     ).toThrow(QueueFullError);
 
+    expect.assertions(5);
     try {
       rethrowQueueError({
         code: "queue_full",
@@ -18,6 +19,7 @@ describe("rethrowQueueError", () => {
       });
     } catch (err) {
       const qf = err as QueueFullError;
+      expect(qf).toBeInstanceOf(QueueFullError);
       expect(qf.queueSize).toBe(9);
       expect(qf.max).toBe(10);
       expect(qf.code).toBe("queue_full");
@@ -25,10 +27,12 @@ describe("rethrowQueueError", () => {
   });
 
   it("defaults missing queue_size / max to 0 when details are sparse", () => {
+    expect.assertions(3);
     try {
       rethrowQueueError({ code: "queue_full" });
     } catch (err) {
       const qf = err as QueueFullError;
+      expect(qf).toBeInstanceOf(QueueFullError);
       expect(qf.queueSize).toBe(0);
       expect(qf.max).toBe(0);
     }
diff --git a/apps/web/lib/api/domains/queue-api.ts b/apps/web/lib/api/domains/queue-api.ts
index b49355d116..3b4d516fad 100644
--- a/apps/web/lib/api/domains/queue-api.ts
+++ b/apps/web/lib/api/domains/queue-api.ts
@@ -33,7 +33,14 @@ type WSError = {
 };
 
 function asWSError(err: unknown): WSError | undefined {
-  if (typeof err === "object" && err !== null && "code" in err) {
+  // Some WS error payloads omit `code` and only carry `message`/`details`;
+  // narrowing on `code` alone would drop those and stringify the whole object
+  // as the eventual Error message ("[object Object]"). Real Error instances
+  // are skipped so they pass through unchanged in `rethrowQueueError`.
+  if (typeof err !== "object" || err === null || err instanceof Error) {
+    return undefined;
+  }
+  if ("code" in err || "message" in err || "details" in err) {
     return err as WSError;
   }
   return undefined;