Sometimes when I send a message, it ends up in the Outbox and won't get sent. When I open the message and look under the delay delivery options, the message has gotten checked for delayed delivery. Even if I uncheck that box and resend right away, it goes back in the Outbox and has been rechecked for delayed delivery again!

I have the same problem. Any help? but in my case, it only happens when I am not at home. so when am connected to any place but home this issues appears. emails stay in outbox and not sent.