Items deleted in Mac Mail do not Delete on outlook.com – HELP

If I delete a message on any of my IMAP connected devices (Mac Mail, iPhone) it will automatically delete on all of my other IMAP devices, but not on outlook.com It appears as though it does not sync deleted messages properly. 

For example, if I get a new email and I delete it on my macbook air, it will delete on my iPhone and iMac, but it will still be on outlook.com in the inbox. 

HOWEVER IT GETS EVEN MORE ODD: 

When I delete something from one of my IMAP connected devices, it will put a copy of the message in the trash, but it still keeps a copy in the inbox, and even deleting it from trash on my imap devices only deletes the copy in the deleted folder online.

This is driving me insane, I just switched from Gmail and this should not be happening. 

So to recap:

I receive a message, read and delete it on my iPhone. The message will automatically remove itself from my MacBook and iMac via IMAP syncing. On outlook.com, the message still shows up, one copy in my inbox, and one copy in the deleted folder.

Please help!!