Currently Being ModeratedJul 2, 2013 11:44 AM (in response to thegame658)
I have seen this issue when the local *.ost file becomes corrupt. I would delete it and let it be rebuilt, maybe leave desktop Outlook in Online rather than cache mode after the *.ost is rebuilt.
Currently Being ModeratedDec 27, 2013 8:15 PM (in response to thegame658)
I started to see this problem a couple of weeks ago. Until then for a few months I had not have any issue.
I found a solution here. The problem in your case is likely the sync between Outlook and Exchange Server.
> In order to have the 'deleted item' actually deleted at the server, you have to got to the 'deleted item' folder and *sync* it.
> Usually once opening the folder it will just initiate a sync, if not, click on the sync button.
When I tried to sync Deleted Items folder, I found it was not synching, and found large deleted email (20MB) probably stuck. I manually deleted it, then started synchronizing.
Now, deleted mail on Outlook is automatically deleted on my iPhone!! :-)
Hope this will solve your problem as well.