I have Outlook 2010 and the Zimbra Connector version 6.0.5981.7 have also tried version 6.0.6089.9.

When I send from Outlook, the email goes out, but it does not show up in the Sent folder. If I send the same email from the web client, and then start up Outlook, that message will be in the Sent folder. Also odd about this is that the email I sent from Outlook that did get sent, does not show up in the web clients sent folder either!
Any ideas?