After we upgraded our 2003 Outlook/Exchange versions to Outlook 2007 and Exchange 2007, the Delay Delivery option will not function for any of our users. The delayed message does go to the user's Outbox as it should, but the message remains there after the scheduled delivery time and never gets sent even if you open the message and try to manually send it. We have confirmed that the messages are not being sent (i.e. it really is stuck in the Outbox). We have also tested this on Terminal Services with the same results. We normally run Outlook in cached mode, but out of curiosity we tested non-cached mode as well with no luck. Any ideas?