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.