diff --git a/src/agents/queue/queue.c b/src/agents/queue/queue.c
index c3f51b6..be725c9 100644
--- a/src/agents/queue/queue.c
+++ b/src/agents/queue/queue.c
@@ -609,11 +609,13 @@ AddPushAgent(QueueClient *client,
     XplMutexUnlock(Queue.PushClients.lock);
 
     /* Queue entries can reach the outgoing queue while the agents are still
-     * registering during startup.  Wake the monitor as soon as the SMTP
-     * delivery agent is available instead of leaving those entries behind
-     * until the normal remote-delivery retry interval expires. */
+     * registering during startup.  A normal monitor restart deliberately
+     * skips young outgoing entries to avoid a tight delivery retry loop, so
+     * merely waking it is not sufficient here.  Treat a newly available SMTP
+     * agent like an explicit flush: retry persisted entries immediately once,
+     * after which failed deliveries return to the normal retry interval. */
     if (queue == Q_OUTGOING) {
-        Queue.restartNeeded = TRUE;
+        Queue.flushNeeded = TRUE;
     }
     return 0;
 }