Problem: Configured an Outbound SmartHost on our Zimbra Server and my larger emails (4 MB or Higher) are getting stuck in the Outgoing Folder and sending duplicates every 10 to 15 minutes. I have to manually clear out the Outgoing Folder. This issue occurs when using Outlook 2003 & 2007 with the Connector and the Zimbra WebClient. Sending directly out of a Zimbra Server (without SmartHost) has no delays or duplicate outgoing emails.

Any suggestions???