troubleshooting Question

Outlook 2016 (Office 365) - Emails Going Straight To Trash

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snake454Flag for United States of America asked on
OutlookExchangeMicrosoft 365
8 Comments2 Solutions22076 ViewsLast Modified:
Hello Experts!

I have a client who I switched to Office 365 12/18/15.  Everything was cool at first, but as of this past Tuesday I have the following issue that I cannot resolve.

Client\Owner has Exchange email accounts for all users.  He wants another 5 Exchange accounts, (Exchange only license on these), setup as pop accounts for various users.  I know...WHY???  Because he wants each user to have their own folder structure and not delete items like you would in Exchange where one user deletes something and it's gone for all other users.

So...I think I have the issue narrowed down to just the owner's PC, or his Outlook 2016\Office365 install.  Let's take one of these pop accounts as an example.  He has a pop account called support@yourcompany.com.  I have this mailbox setup as a pop in his Outlook and 2 other user's Outlooks.  Something on his PC is deleting all email from "the server" whenever his Outlook calls for mail.  I have this set to every 5 minutes but it happens if he does a manual mail pull as well.  When his Outlook pulls mail on support@, the messages download to his Outlook and immediately delete from the server inbox.  They go straight to "trash", bypassing the Deleted items folder.  I can see these messages in the server's Trash folder when I click on "Retrieve messages that were recently deleted or emptied from this folder, (the Deleted Items folder).

If the messages are not in the server\Exchange inbox...and his Outlook pulls mail before the other 2 users Outlook pull mail...the other 2 users never get new messages sent to the inbox.  The owner is also getting a LOT of duplicates in his inbox.  Duplicates that he deleted 2-3 times yesterday, are coming back in to his Outlook inbox again today...sometimes 5\8\10 times.

What I have tried:
Did a Office365 online repair and a full blown Office 365 uninstall\reinstall.  Created a new profile for just the support@ email. Issue persists...using both a new data\pst file and the old 1.7GB pst file.

If I uncheck Delivery\Remove from server in 14 days...keeping Leave a copy of the message on the server checked...emails "stick" in the inbox on the server and the other 2 users get all the mail from this support@ account.  Unfortunately his duplicates seems to increase after unchecking remove from server.  I have not made any changes in the other users Outlook profiles because I really think this issue is happening only on the owner's PC.  If the owners Outlook is closed...the issue does not occur!

One other thing...as I said the owner has 5 Exchange accounts in his Outlook setup as pop accounts, and one "regular" Exchange account setup as a true, (not a pop), Exchange account.  Emails are getting deleted from all 5 pop accounts just like I have described above.

Any ideas?  He is getting real irritated with me and I may lose the account if I can't fix this issue immediately.

Thanks in advance
Mick
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snake454

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