Apple Mail Stuck on Moving Messages - Ventura 13.3.1

I regularly get things stuck while moving with Exchange and have had this problem for a number of OS versions - it's not new to Ventura. I also have a fairly large amount of mail, 40G of which is on Exchange.

The bad news is there's not a great fix. I've tried all the restart in safe mode, delete the cache files, etc. "try this" options I've found, and very few things I found helped.

From everything I've worked out dealing with this for the last few years, if it's not what Sparks0829 posted above about a bad file or character then it means your directories are out of sync and Apple Mail and Exchange don't get back in sync gracefully. As you suggested, this is why you can't see the threads - they are in "move limbo" and haven't actually moved into those folders on the Exchange side and so don't show up in searches or the folders you think they are in (If you look via OWA or a different app, you'll find them all still in your inbox on Exchange). My main system is still on Monterey, but this hasn't changed in years, so I'm pretty sure it's accurate for Ventura as well.

If I catch it while I still know what email has moved, I can rebuild all the mailboxes concerned (include inbox, trash, junk, sent, and any mailbox you've tried to move things to by hand or with rules). Once it's done rebuilding them all, if you got the offending stuck mail, it's in sync again and good for a while. Depending on your uplink speed and the rate limiting on the Exchange server this can take a few hours to a few days.

Your inbox will fill back up with the things Apple Mail tried to move but Exchange thinks hasn't really moved because they are out of Sync, and you get to file all of them again.

The second way I've fixed this is to close Apple mail and use Outlook (I use web) or iPad/iPhone to manually move or delete the stuck messages. Again this only works if you can figure out which message(s) are stuck, or do all of them back to the last time it worked. If you get the one that stopped things up, next time you launch Apple Mail it should be able to make progress - after it thinks for (quite) a while - and you'll get a number of those "I couldn't move the file" dialogs" for the things it was stuck on that you moved out from under it.

The third way, and the only one that works 100% of the time, is delete the Exchange account, let everything erase out of the account, reboot, then add it back. It's going to be a pain with 75G of mail (it is for 40G) but if you're at 2400 messages not moved, you might need to. This is critical or you'll be doing it all again: don't file any email using Apple Mail until it is back in sync (which for me is from 1-2 days at work with a 1G connection to nearly a week from home). You can use iPad or OWA, etc. to deal with your inbox, but not MacOS Mail until all the folders are downloaded and re-synced or you risk something else getting stuck.

Good luck, and I hope this helps!

-debbie

Hi there JRD67357,

This could potentially be an issue with invalid characters or the files being too large:

If you have an IMAP account and are unable to move messages, it’s possible the messages contain invalid characters (typically added by a mail server) or are too large, or you exceeded the storage limits set by your email account provider.

Have a look at this link for more information: Move or copy emails between mailboxes in Mail on Mac - Apple Support

Keeping that in mind, are you able to move emails to a different mailbox in Mail for other accounts, or is this only happening with your Exchange account?

Thanks!

This happens to me once in every couple of months, and had to sync nearly 100G of mailbox all over again, where resync from office 365 takes several days to a week.

I keep looking online whether any new solution from Apple mail every time it happens, but nothing else. No option in Mac Mail to cancel/rollback this stuck "moving" transaction. It is forever stuck in moving unless account is deleted and add again.

Hoping to see a real solution soon from Apple.

Thank you for the encouragement. I took the past of least resistance and used your "100%"solution, and it worked fine. It took a little under 30 hours for my Exchange account to get reestablished.

I'm confused about something, though. The way I work is that I save all the emails that I care about on my Mac, and delete the ones that I don't want. I would have thought that meant it would take almost no time to get my account back up. However, looking at the info on Mail, it seems it was downloading several hundred thousand files.

Is there some place on Exchange where I can find these files and trash them all, mainly in case this ever happens again? Or, do I need them there even if I've moved them (or so I thought) to my local computer?

Hi jimnap

Sorry I missed this for so long - apparently I don't have it set to alert me to replies.

A couple of thoughts - when you save it on your mac, are you "moving" it into a folder in the "On My Mac" part? or just making a folder under the Exchange part?

if you're doing the On My Mac part, I've run into times I thought I had trashed things, and it had gone past the 30 days I tell it to leave it in the trash, but on Exchange it's still in the trash, or it's tagged it as "deleted but recoverable" and I need to go into that part of the "Trash" through outlook.office.com and basically tell it to yes, really delete my trash. there is also a setting about how long to keep files in the Trash in the Mail.app that comes in to play as well.

If you make a folder to file them in, but it's under the Exchange header, it downloads a copy to your mac, but files it into a folder of the same name on the Exchange server, and then it doesn't even try and delete them on the exchange side.

hopefully some of that is useful!

-debbie

scherel wrote:

Hi @Debbie:

Thank you for this summary, the best post I've seen so far after multiple days of research.

I have a question for you though that I'm missing in your solution #3. When you add back the Exchange account do you expect the copy to automatically reinitiate where it was blocked or should we manually start copying everything back again. In case of the latter how would MacOS Mail handle the duplicates of messages already copied?

To clarify here I am copying and not moving messages.

When you do solution number 3, you delete all state of where things are, so it will add back all the messages still on Exchange, to whatever folder (inbox or other) that they are still in on the server side.

So any that had successfully copied to a new folder should be in that new folder (either on Exchange or the OnMyMac or wherever you were copying to). Any that weren't are just where ever they are on the server. Nothing will restart, because Apple's Mail.app doesn't know anything about what you were doing before that. #3 is the "nuke it from orbit and start again" version.

If you start copying again, the mac will copy it again, and in my experience you'll now have 2 copies of each message in the folder you were trying to copy for anything that was previously successful if it's in the "On My Mac" part.

As far as I know, there is no elegant way to do what you sound like you want - the closest I can suggest is if that everything is still on the server, rename the folders you were copying to and start all over again with fresh folders. try and find the mail/files that stop things up, delete them or move them to a "don't copy" folder, until you get everything moved. Anything you do with #3 is brute force.

good luck!

-debbie

Hey there JRD67357,

If everything is set correctly, see if the issue continues in safe mode. These steps can isolate the issue and tell us if there is a certain app, other software, or setting causing this. You can read how to do this here:

• Start up your Mac in safe mode

1. On your Mac, choose Apple menu  > Shut Down.

2. Wait for your Mac to shut down completely. A Mac is completely shut down when the screen is black and any lights (including in the Touch Bar) are off.

3. Press and hold the power button on your Mac until “Loading startup options” appears.

4. Select a volume.

5. Press and hold the Shift key, then click Continue in Safe Mode.

6. The computer restarts automatically. When the login window appears, you should see “Safe Boot” in the menu bar.

If the issue doesn’t continue in either of those, then you may want to review your Login Items as seen here:

• Remove login items to resolve startup problems on your Mac

We hope this helps. 

Take care. 

I found this article helpful, and #5 helped me figure out I can rename the folder on iCloud webmail to get the app to recognize the folder involved—after the Mail app crashes first. Steve Jobs has definitely left the building on this one

I think an older version of the Mail app showed an interactive progress indicator that let you stop and restart the sync process to wake it up from a bad communication—like a refresh button in your web browser. Would be nice if they brought that option back. It's the little things, really. Or as Charles Eames, said: "The design is the details."

https://www.cigatisolutions.com/blog/apple-mail-moving-messages-stuck/#5_Delete_the_Target_Folder_from_iCloud

I almost switched back to Gmail out of frustration before figuring out this one weird trick

Thanks for this information Debbie. I'm in a similar situation ... trying to port outlook.com mail into iCloud.com ... I have roughly 35Gb (1,000's of folders and 1/4 million emails) ... I tried using the iCloud.com cloud based import (no computer involvement) ... that ran for 4 days ... after it finished, I started looking through my folder structures only to find out 100's of folders and 1000's of emails didn't port. there was no exception listing to the import process. The process/problem is detailed here: iCloud Mail Import Finished - missing man… - Apple Community

I then tried using the Mac OS MAIL drag/drop method (selectively pulling over groups of folders ... not all at once) ... and like this thread describes, I occasionally receive a "cannot copy" pop-up, which of course freezes the "sync'ing" ... and I can find no method to cancel the folder drag/drop activity ...

I'll probably have to do what's described in this thread ... delete my outlook.com Profile from Mac OS MAIL ... reboot ... re-add it ... and then find some other method to port large volumes of mail.

kind of regretting trying to move all my mail to iCloud.com ... really, the only reason I wanted to utilize iCloud.com mail for storage ... is ... mail encryption at rest ... no other reason ... I may, in the end, just decide to keep my mail completely 100% stored offline ... not sure at this point.

I found out that pressing the refresh button on webmail gets the desktop interface to update its information. Who'da thunk?

Hi Debbie/djf54321,

Thank you for the encouragement. I took the past of least resistance and used your "100%"solution, and it worked fine. It took a little under 30 hours for my Exchange account to get reestablished.

I'm confused about something, though. The way I work is that I save all the emails that I care about on my Mac, and delete the ones that I don't want. I would have thought that meant it would take almost no time to get my account back up. However, looking at the info on Mail, it seems it was downloading several hundred thousand files.

Is there some place on Exchange where I can find these files and trash them all, mainly in case this ever happens again? Or, do I need them there even if I've moved them (or so I thought) to my local computer?

Thanks.

I have the same problem happening. I do Debbie's "third way" mentioned above.

But I have to do this every other week for my email to function. This does not see right.

Any more permanent solutions?

Thanks,

Jack

Hi @Debbie:

Thank you for this summary, the best post I've seen so far after multiple days of research.

I have a question for you though that I'm missing in your solution #3. When you add back the Exchange account do you expect the copy to automatically reinitiate where it was blocked or should we manually start copying everything back again. In case of the latter how would MacOS Mail handle the duplicates of messages already copied?

To clarify here I am copying and not moving messages.

Thank you.

I have been having this problem for years. I'm a university professor with multiple (6+) macs I need to work at in the lab, office, home, travel, etc. It's insane that this problem has persisted for so very long. My wife keeps saying "ditch the mac and use Outlook on a pc." That's a solution, it appears. Otherwise, I do think it is on Apple to sort this out gracefully and permanently. Dear Apple - please, please fix this!

After renaming and forgetting to sync the desktop version before doing a rebuild, I managed to break the webmail client. It said a folder that had failed to sync before the rebuild "no longer exists."

I renamed the folder back to the old name on desktop, and it erased the subfolders even though the subfolders are visible on webmail. Proceed with caution when renaming. It's probably best to synchronize before a rebuild—but you would think something labeled "rebuild" that is meant to fix things would already do that.

The desktop version broke too after renaming, showing a gray folder with the old name that "does not exist." Apple needs to work on the sync logic around renames on both ends. I'm working around it by moving the disappeared web content into a new folder. Fingers crossed it updates properly, eventually. Message download on the desktop client is really slow