Duplicate emails in sent folder

How do I eliminate duplicate emails in my Mail sent Folder? I am using Apple Mail 16 on iMac Monterey 12.6.7 with a hotmail (Outlook) account. There are lots of suggestions on line but none of them work (though they might have with older software versions on Mac or Outlook).


I have no Rules set up in Mail > Preferences > Rules for my account and i tried remove my hotmail account from the Mail app on my Mac, as suggested by MichaelB2019 (Community Specialist) in a pass conversation with the same title, but after reconnected my hotmail account i didn't trigger it to fix itself and the same problem reappeared.


This problem does not occur when I use Mail on my iPhone or Outlook app and Outlook online on my mac, so I presume the source of the problem is Mail on my mac.


Any ideas on a fix ?

iMac 27″, macOS 12.6

Posted on Jun 26, 2023 11:26 AM

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Jun 27, 2023 4:48 PM in response to Dodier007

Hello Dodier007,


It seems you have isolated the issue to your Mac. Let's see if we can isolate it a bit further.


We would suggest starting up the system in what is called safe mode. Safe mode only loads what is needed to run the computer. This can help isolate what is causing issues.


To start in safe mode, follow these steps:


1. Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.
2. Release the key when you see the login window, then log in to your Mac. 
3. You might be asked to log in again. On either the first or second login window, you should see ”Safe Boot” in the upper-right corner of the window.


More information is available here: How to use safe mode on your Mac - Apple Support


The computer will take longer to start in safe mode, and the screen may have some distorted video as it starts up. This is normal. Once you are logged in, check the mail app and see if the same issue occurs..


If everything seems to work as expected, go ahead and restart the computer normally and test again. There are steps outlined on what to do if the issue does or does not continue in safe mode.


Starting in safe mode also forces the computer to run some disk checks similar to First Aid. This can actually resolve some issues.


Have a good day.

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Duplicate emails in sent folder

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