Can't delete emails with Monterey update

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Level 1

8 points

Can't delete emails with Monterey update

What is the issue with emails not being able to be deleted with Monterey? I use Apple Mail and recently upgraded to Monterey version 12.3.1. I try deleting emails over & over and they just show back up. It's a massive time suck trying to keep my Inbox clean.

Has Apple addressed this issue at all since releasing Monterey last year? I've seen similar threads about rebuilding your mailboxes and all kinds of other time sucking activities that don't seem to work.

Is there a real solution to this problem? Thank you.

MacBook Pro 15″, macOS 12.3

Posted on May 10, 2022 7:48 PM

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Answer 1

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guinness0044 Author

Level 1

8 points

May 27, 2022 6:54 AM in response to guinness0044

I finally figured out the problem on my own since I couldn't get any help here, so I wanted to share the solution.

I went into Mail > Preferences > Accounts, and under each of my email accounts "mailbox behaviors", I found that some of them had "None" marked for their Trash Mailbox. Evidently this is why the mail would not go to trash and would just reappear in my Inbox. Somehow in the upgrade to Monterey, these mailbox behaviors were changed.

It seems the problem is solved now. Thank you to those who tried contributing solutions.

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Answer 2

May 11, 2022 7:19 AM in response to guinness0044

Being a gmail account does not immediately tell us whether it is configured as IMAP or POP. Both possibilities exist.

I am guessing that yours is probably configured to use IMAP.

To be certain, go to Mail->Preferences, then click on Accounts. Each account will be labelled as IMAP, POP or Exchange.

I have one gmail account as POP and a different one as IMAP.

I am sorry, I don't know the cause of this.

When such a situation occurs, you may want to test by deleting the offending mail using gmail web interface.

I expect it won't recur after that. Does it?

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Answer 3

May 11, 2022 2:32 AM in response to guinness0044

This looks like a syncing problem with your mail server.

You need to provide more information, as P. Phillips requested.

In particular, what type of account - IMAP, POP, Exchange...

FWIW, I have several accounts of all those types, and I have never seen this, or heard any similar complaint.

It is far more likely to be something particular to your account setup. If everybody were suffering from this the outcry would have been huge.

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Answer 4

guinness0044 Author

Level 1

8 points

May 11, 2022 7:04 AM in response to PRP_53

In answer to your question as well as the same question from Luis S., all accounts set up in my Apple Mail are Gmail accounts, which means POP3 server I believe. No changes were made to mail accounts before/after upgrading to Monterey, so I'm not sure how my mail set-up can be wrong now....

Note, not all emails keep reappearing after deletion, only certain senders it seems. One example is Google though, calendar reminder emails keep reappearing.

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Answer 5

PRP_53

Level 10

85,681 points

May 11, 2022 7:09 AM in response to guinness0044

Thank you for clearing up that information.

To be honest - will step back on this one as Google and I do not mix well. ie - limited positive / success it assistance where Google anything comes into play.

Nothing personal but a personal preference.

Am confidence @ Luis S will step up :-)

EDITED

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Answer 6

guinness0044 Author

Level 1

8 points

May 11, 2022 7:09 AM in response to Luis Sequeira1

Luis, I replied to Philip above that the email accounts are Gmail accounts set up in Apple Mail.

Also, if you google "emails not deleting from apple mail after upgrade to Monterey", you'll see plenty of results that speak to this exact problem from other users, so mine is definitely not an isolated case (especially considering mail has worked fine for me for several years and this problem started immediately after upgrading to Monterey). It's not a coincidence I do not think....

Thanks for any suggestions you might have.

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Answer 7

guinness0044 Author

Level 1

8 points

May 11, 2022 7:31 AM in response to Luis Sequeira1

Thanks Luis. They are all IMAP accounts.

The problem with the emails is not that they are offending emails, they are emails I want/need to read. So I need them to come to my Apple Mail on my computer.

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Answer 8

May 11, 2022 7:37 AM in response to guinness0044

guinness0044 wrote:

Thanks Luis. They are all IMAP accounts.

The problem with the emails is not that they are offending emails, they are emails I want/need to read. So I need them to come to my Apple Mail on my computer.

I understand that.

IMAP is supposed to sync your client to the mail server: when you delete, move or edit on your mac, changes should reflect back at the server, and vice versa.

It appears that, for some reason, the deletion is not syncing back to the server, and then your mac resyncs to what is (still) on the server; that is how the messages reappear.

Since this seems to occur only for some messages, the workaround is to open gmail using your browser and deleting them there, effectively deleting the problem messages on the server side.

I was not suggesting you stop using the e-mail accounts, just "force-delete" those messages that you wanted to delete, but were reappearing.

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Answer 9

guinness0044 Author

Level 1

8 points

May 11, 2022 7:35 PM in response to Luis Sequeira1

Luis, thank you again for the response and the info, that is helpful.

Question: since this syncing issue didn't exist before I upgraded to Monterey, do you know what the problem could be, any specific possibilities? I don't want to resort to workarounds, I don't generally access email online. Apple knows this problem exists with Monterey, I would rather find a solution that solves the issue directly.

Thank you again for your help, much appreciated.

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