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

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
snake454Asked:
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Scott CSenior EngineerCommented:
Check for any rules that may have been created that are doing this.  This is my best guess.  He probably set up some rules to "manage" all of his accounts and bungled something up.

If everything was working and now it isn't...something has to have changed.  Outlook just doesn't delete emails on its own.
snake454Author Commented:
No rules in his Outlook or on the "server side".  Thanks!!
David Johnson, CD, MVPRetiredCommented:
you will have to check every machines pop settings to ensure that remove download from server is NOT turned on. POP3 is not designed for multiple users. Users cannot always get what they want and making specific choices mean you have to live with the results.   All it takes is one of the additional users or the user to make a change and the entire house of cards will fall down.

perhaps the support@domain.com should not be access by any human but have a rule set to forward a copy to the distribution list of the owner and his support staff email.
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snake454Author Commented:
Thanks David!  I totally agree..."pop3 is not designed for multiple users".  Client would counter that "well it was working fine two days ago".

The first thing I checked on all PCs using this pop account was leave messages on server.  All are set correctly. If I check leave on server...and uncheck delete after 14 days, it works...but duplicates in his inbox, (only), increase.

Further agree that using pop accounts this way is indeed a house of cards.  Client is has always been a "pain in the A**".  Refuses to buy new workstations only lets me get refurbs.  Ran pops provided by ISP for years, until I finally got him on Office365 and then here we go again back to pops!  While he is a pain, he is my third biggest client and as such, ($$$), would hate to lose him but I may.

Finally, MS Office 365 support also suggested distribution lists, but client won't like that because they would go\co-mingle with their main\Exchange account.
David Johnson, CD, MVPRetiredCommented:
what is happening is the last downloaded message pointer is getting reset on the server everytime someone does a send receive.. perhaps adding an outlook addin that removes duplicates i.e. https://www.mapilab.com/outlook/duplicate_remover/  (install for all users when prompted) [works well]
snake454Author Commented:
Final update...

After seeing that this issue was MS\Outlook2016 related I seized the opportunity to use all this client unhappiness to convince the client to switch these pop accounts over to Exchange.  End of duplicates and missing emails!

Thanks for all your help and for taking the time to respond.  I'm going to award some points to David Johnson for his spot on comment: POP3 is not designed for multiple users. Users cannot always get what they want and making specific choices mean you have to live with the results.   All it takes is one of the additional users or the user to make a change and the entire house of cards will fall down.

Thanks again

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snake454Author Commented:
I found KB3145116 on my own, but liked David Johnson's comment:

POP3 is not designed for multiple users. Users cannot always get what they want and making specific choices mean you have to live with the results.   All it takes is one of the additional users or the user to make a change and the entire house of cards will fall down.

Thanks Everyone!!
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