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Monterey upgrade from El Capitan mail accounts not working

I've bought a new MacBook air and migrated all my stuff from an old 2009 MacBook Pro running El Capitan (10.11.6)


Everything seems to have come over but Mail isn't recognising the mail accounts. The Mail folder in Library looks like it should, V9 folder with all the subfolders and support files corresponding to the El Cap Mail folder, but Mail wants me to enter passwords for the accounts.


When I did that on one of the accounts, it started downloading 50,000 emails going back several years, so Apple Support told me to do and erase from System Prefs and do the migration again. This gave the same result with the Mail accounts.


I've got a time machine backup of the MBP going back sometime that I did the migration from.


Anyone got any ideas on getting the Mail accounts re-established.

MacBook Air 13″, macOS 12.0

Posted on Feb 8, 2022 8:40 PM

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Posted on Feb 9, 2022 1:20 PM

First try:

Try booting to Safe Mode. That boot up takes minutes and clears caches and other things that may resolve your problem.

How to use safe mode on your Mac - Apple Support

A lot of times just boot to Safe Mode followed by normal boot resolves problems.


Next, go to System Preferences>Users & Groups and create a new user. Log in with that users and see if Mail works after you set up an account.

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Question marked as Top-ranking reply

Feb 9, 2022 1:20 PM in response to graeme38

First try:

Try booting to Safe Mode. That boot up takes minutes and clears caches and other things that may resolve your problem.

How to use safe mode on your Mac - Apple Support

A lot of times just boot to Safe Mode followed by normal boot resolves problems.


Next, go to System Preferences>Users & Groups and create a new user. Log in with that users and see if Mail works after you set up an account.

Feb 16, 2022 12:14 AM in response to graeme38

Finally got it sorted. The problem was with the auto complete functionality in Mail, it thought that the only possible connection to my email provider was by IMAP and didn't have settings stored for POP3. This broke the mail import as my accounts were set up POP. And trying to enter the accounts using the Add Account window wanted to set up an IMAP account, not the POP we use.


The solution was to enter an email address with a fictitious provider (I used an email on a domain I knew didn't have email) with the password for the account I wanted to set up, then when I pressed enter it brought up the option to choose POP then edit the email address to the correct one, then manually enter the server details. Press enter and the POP accounts set up just fine. I then imported the mailboxes from my old Mac and now up and running on my new MacBook Air.


Thanks to all the people at Apple Support who dealt with a very frustrated customer, but taught me a lot and made the final setup a lot quicker, and to Tasha at my ISP who said edit it and see what happens.

Feb 8, 2022 11:58 PM in response to graeme38

Up to OS X 10.10 I could do a clean install and just copy the old ~/Library/Mail folder from the old system to the new as is and Mail started using it.


But with the clean upgrade to El Capitan and later that no works. In El Capitan I tried to export from old system and then import that to new system but experienced either missed or duplicated messages. I went through some hoops and in the end I used Emailchemy ($30) to export Apple Mail OS X 10.10 mail files as mbox. Apple Mail OS X 10.11 imported them OK.


After that the following has worked for local mail in the new clean system (I first enable gmail and iCloud cloud mail in system preferences):


Mail > File > Import Mailboxes... > Apple Mail > choose [Mojave - Big Sur] ~/Library/Mail folder > choose all Items.


On the left-hand-side under "On My Mac" > Import, ..., look for and move "Local" and all mailboxes inside it up under "On My Mac". Right-click and delete "Import" folder (it has gmail mailboxes that are online).

Feb 9, 2022 12:41 AM in response to lllaass

The email accounts are POP and are kept on the server the accounts download to several computers. Hence the huge number of emails that want to download if I try and set up a new account.


There has to be a way of getting Mail to recognise the mailboxes that have been migrated. It's all there, just Mail doesn't see it.


I've since updated Monterey from 12.0.1 to 12.2 but that didn't help.

Feb 9, 2022 10:55 AM in response to Matti Haveri

Ok, the plot thickens.


I managed to get into Mail by creating a burner Gmail account, tried iCloud first and that crashed Mail and existing Gmail account wouldn't let me in saying the account already existed.


So I get to the import dialog, select the Mail folder from ~/Library/Mail from my old mac which had been copied to desktop, but when I choose that Mail freezes and has to be force quit.


The freezing and crashing doesn't look good here, something is not right.

Monterey upgrade from El Capitan mail accounts not working

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