Windows 7 - Messages Stuck In Outbox (Non-Cached Mode + Delegated Mailbox)

If a user has their Outlook profile set to NOT use Cached Exchange Mode, and attempts to send an email from a mailbox they've been delegated access to, the message ends up "stuck" (for a lack of a better term) in the user's own Outbox and never leaves the Outbox, or moves to the Sent folder.

We are running Exchange 2010 SP2 on site, and our clients are connecting to Exchange via Outlook 2010 SP1.

Hi,

Have you tried repairing the Outlook installation via the Control Panel?

If all else fails, creating a new profile should fix the problem.

So this all seems to be related to the "DelegateSentItemsStyle" registry key setting. A while back we made it mandatory that all items sent on behalf of a delegate must be saved in the mailbox owner's sent items (DelegateSentItemsStyle=1). As a test I set this key to "0" (disabled the key in other words), sent a message as the delegate, and the message left the Outbox immediately and saved to my own Sent Items.

While I'd prefer to not disable this registry key (because this feature was very useful when a mailbox was shared amongst 10 users), I guess if we want to run Outlook 2010 in online/non-cached mode this is the only way!

http://support.microsoft.com/kb/2181579