diff --git a/src/Wolverine/Envelope.Internals.cs b/src/Wolverine/Envelope.Internals.cs
index 74b4bf6d3..585d916cb 100644
--- a/src/Wolverine/Envelope.Internals.cs
+++ b/src/Wolverine/Envelope.Internals.cs
@@ -240,7 +240,24 @@ internal async ValueTask QuickSendAsync()
 
         _enqueued = true;
 
-        if (Sender.Latched) return;
+        if (Sender.Latched)
+        {
+            // If the sender is latched, it indicates that the endpoint is currently unavailable 
+            // (e.g., due to a network disconnection or a failure in the transport).
+            // In such cases, we should *not* attempt to send the message immediately.
+            //
+            // Instead, if the sender is a SendingAgent, we explicitly mark the envelope as failed 
+            // so that it will be retried later when the connection is re-established. 
+            //
+            // This conditional block ensures that latched agents skip enqueuing the message, 
+            // but still track the failure to maintain durability and retry logic.
+            if (Sender is SendingAgent sendingAgent)
+            {
+                await sendingAgent.MarkProcessingFailureAsync(this, null);
+            }
+
+            return;
+        }
 
         if (Sender.Endpoint?.TelemetryEnabled ?? false)
         {