Messages are getting stuck in the Outbox
Make sure Outlook is not set to work Offline
- Click on File
- Click on Work Offline (should uncheck the item)
- Click Send/Receive
If Outbox doesn't begin to clear move the messages to the Drafts folder and send yourself a message. If the message leaves the Outbox one of the messages that was moved to the Drafts folder is most likely causing the problem.
- Click on the Drafts folder
- Open a message and click Send
- Repeat until a message stays in the Outbox, the message that stays is the one causing the problem.