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For some reason all my PM's are in outbox but not sent messages which I assume means they didn't send.

Any idea what could be going on?

They will sit in outbox until they are read.

Exactly. Also try clicking on the name of the person you sent the mail to and view their profile to see when they even last logged in. They may have not been online for quite a while or maybe just don't notice the mail notice, especially if they didn't set the option to have the popup (or did and a pop up blocker is blocking it).