Microsoft Exchange: Server not deleting messages deleted or moved with Mail

Are you dragging the message out of the Exchange Inbox to the local "On My Mac" folders?

If yes, you are copying the message.

To Move...

• Use the Move icon to move the message
• Use command-drag.

This will force a move instead of a copy. it works just like drag in files in the Finder - between different servers (and moving from an exchange or IMAP folder to a local folder is moving between server) the file/email is copied by default.

Cmd-drag forces a move instead. Dragging between different folders on the same server moves by default, but a copy can be forced by holding down the Option key when dragging.

FWIW, the Microsoft Exchange with Office365 that many companies use now offer 50GB of space. While you wouldn't be running out of room, you certainly don't want duplicates piling up in your mail app. We used to have options to remove duplicates but sadly most of those options no longer exist.

I have noticed the same problem for months! Only on exchange server, and only when using Apple Mail. If I delete message on my iPhone, or using OWA it works perfectly. On Apple Mail it's about 50/50 whether it deletes or not. I am currently still on 10.11.... any idea if this still a problem on 10.12?

Mail 10.12.1 has issues with Exchange. I would not update until this is sorted out.

If I delete message on my iPhone, or using OWA it works perfectly. On Apple Mail it's about 50/50 whether it deletes or not.

Apple Mail and Outlook for Mac both talk to the MS Exchange server using a Microsoft protocol called EWS - Exchange Web Services. However iOS devices will normally talk to the same MS Exchange server using a different Microsoft protocol called EAS - Exchange Active Sync. Changing from Apple Mail to Outlook for Mac will have no effect at all on your iOS devices which will continue to use EAS. iOS devices cannot speak EWS and Apple Mail and Outlook for Mac cannot speak EAS.

The Mac and iOS devices do not want or need to sync directly to each other, rather they both talk to the same account on the same MS Exchange server and via that get the same Email, Calendar and Contacts entries.

Note: folders with large numbers of messages can be more difficult to sync. How full in your Inbox? Do you have subfolders under the Inbox?

Inbox

Subfolder A <----this is wrong

Drafts

Sent

Junk

Trash

Subfolder A <----this is correct

Hi Diane!

Nope, no subfolders in my inbox, and just to be clear, mail on my iPhone deletes perfectly. It's just Apple Mail on my mac. Once a week or so I have to pull out my phone (or Office365 web access) and delete all the messages I'd already deleted on my Mac, then it seems to sync properly. I never have more than 100 in my inbox, though I do have many very full folders (not in my inbox)

The difference between EAS and EWS is why the iPhone works correctly. It's more difficult to get Mail working correctly with EWS. In addition, Apple Mail is a not fully featured Exchange email client like Outlook.

I tried all of the suggestions that I found on the forum but resorted to deleting my Outlook account from my iPhone and re-installing from scratch. This worked! I didn't lose any emails apart from the ones that I had been unsuccessfully trying to move to Trash.

Open Mail > Preferences > Accounts

Select your Exchange account

Click on Mailbox Behaviors tab > check your settings for trash.

Do the same for your Exchange account on your iPhone.

No, different problem. That setting determines if and when the trash should be deleted from the server (that is, email that has successfully been moved to the trash folder). The problem I and others are having, is about half the time, when I delete a message in Apple Mail, it reappears. So for example, I'll spend 30 minutes cleaning up my inbox, only to find later many or all of the emails still there (or reappeared). I've tried deleting and reinstalling the account, only temporary fix.