Apple Mail is constantly trying to send email that cannot be deleted

Apple Mail tries to send mail all the time

A reader recently wrote to me about a problem with their Mac with Apple Mail. Well, now many will say: It is clear that you have problems when you use this mail client, but I also like to use it and can understand that you are reluctant to change programs here, just to get some problem out of the way to go.

Apple Mail is trying to send large emails and will not finish

In any case, my reader had tried to send some large audio files (> 50 MB) to friends via email. The files have arrived at the friends, but the mail program continues to report in the corner below:

14 out of 16 emails are being sent ... 54,7 MB

The funny thing is that even waiting a long time does not bring success here, but the files keep increasing. Eventually it said "Sending 18 out of 20 emails...54,8 MB".

You can find out what Apple Mail is doing at the moment using the "Activity" menu item.
What Apple Mail is currently busy with can be found out via the “Activity” menu item.

First Tip: Apple Mail Activity Window

My first tip was to go to the "Activity" option in the "Window" menu in Apple Mail. This will bring up a small window where you can see Apple Mail's current tasks. As a rule, the sending process can also be completely removed via this list if Apple Mail hangs. Unfortunately, this did not work for my reader. He saw the process in the list, but couldn't delete it.

Mails that are listed in activity cannot always be deleted.
Mails that are listed in activity cannot always be deleted.

Second tip: look for the mails in the mail folder

My second idea was to look directly in the folder structure of Apple Mail to see if the mail files could not be deleted. To do this, open the library folder (explained here) and then go to the Mail folder. In the best case, you make a copy of the mail folder beforehand by marking it and duplicating it with CMD + D.

In the mail folder, all the mailboxes are located in the “V7” folder (with macOS Catalina), in which you can find the “.mbox” files that contain the mail data. You can enter the individual files using the space bar quick look look at it and possibly track down your unsent emails and drag them into the trash by hand. However, the emails were not found for my reader Wolfgang.

I was at the end of my game and had to pass. Something that I really hate to do.

PRAM reset does the job

A day later I got an email from Wolfgang that Apple Support could finally help him. He shut down his Mac and then restarted it while holding down the CMD + ALT + P + R keys. Some also know the keys as Command + Option + P + R.

When restarting the Mac you hold these keys down until it has done the "bling" a few times. Then you let go so that it can boot up normally. The whole thing is called "PRAM-Reset" (Photos: Sir Apfelot).
When restarting the Mac, hold these keys down until it blings a few times. Then you let go so that it can start up normally. The whole thing is called a “PRAM reset” (photos: Sir Apfelot).

With this key combination you solve one PRAM reset, which I also explained here. After the restart, Mail was fully functional again and the strange message about the mails that would be sent was gone.

Sometimes there are completely unexpected solutions, because I never thought that a PRAM reset could be related to an Apple Mail display, but apparently it is. If you also have the problem with an “undeletable” e-mail that gets stuck when sending, you can see whether one of the three approaches helps.

Update 15.05.2020/XNUMX/XNUMX: A reader just wrote me that rebuilding the mail index could also fix this problem. If you want to try it, you will find here are the appropriate instructions from me.

My tips & tricks about technology & Apple

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8 thoughts on “Apple Mail keeps trying to send email that cannot be deleted”

  1. Marty Shellman

    Unexpected solution. Because I wonder what PRAM has to do with emails ...

    On the other hand, a friend asked me why Safari always crashed when starting up in her main user account, but not with the guest user. Then I tried a few things, including deleting preferences, etc. It didn't work.

    The Apple support that was then contacted recommended reinstalling the entire system from recovery, which took almost 7 hours. After that it went without any problems. The tip made me frown, but then it probably worked.

    Unusual problems sometimes require unusual solutions ...

  2. In the past (so 9 years ago ... God was with me a long time ago) I often got mail in the activity display. Then no more emails came in because Mail kept clinging to an action.
    The solution was to delete .OfflineCache in ~ / Library / Mail / and in the sub-folders ...
    Since the mail app has received several updates in the meantime, probably obsolete ;-)

    1. Hello Hubi! The “.OfflineCache” folder also exists under macOS Catalina. I just checked! Thanks for your tip! :D

  3. super thanks, the (opt-cmd-pr-) solved my problem in the mail program.
    The hanging mails had always confused me. I could not assign this action.
    Now the ad is gone. That pleases me very much.

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