iCloud Mail: Can't connect to the account "iCloud". Enter the password for user "".

[Buadhai]

This on an M1 MBA running 13.5.2

Suddenly I cannot send mail from this machine using an iCloud mail address. The mail fails with the message:

Can't connect to the account "iCloud".
Enter the password for user "".

Connection Doctor says that the iCloud SMTP server is down with the following error:

READ Sep 22 15:15:03.104 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.mail.me.com -- port:587 -- socket:0x6000026953e0 -- thread:0x60000177fc40
501 5.7.0 Authentication aborted


WROTE Sep 22 15:15:03.105 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:smtp.mail.me.com -- port:587 -- socket:0x6000026953e0 -- thread:0x60000177fc40
QUIT

Connection Doctor on my old iMac says that both the IMAP and SMTP iCloud servers are up.

I am able to send iCloud email using my iPhone and the old iMac. It's only the new M1 MBA on which it fails.

Looks to me like Mail is either not sending the user name or password causing the "Authentication aborted" message.

But, I'm not sure how to fix this. The rest of iCloud (photos, drive, etc.) is working fine, so I'm doubtful that logging out of iCloud would help at all. It must be something else.

I did try restarting the machine, restarting Mail, turning iCloud mail off and on.

Any ideas?

[edit] - I just went in to System Settings > Apple ID > Password & Security and got this interesting message:

 

[Buadhai]

I finally contacted Apple Support and this was the last word:

It seems to be an issue with the system at the moment Michael. I really apologize for the inconvenience.

So, I guess I just wait.

 

[dancefreak]

I can't login to iCloud at all from MacBook Pro M2 as of today.

 

[Buadhai]

I finally contacted Apple Support and this was the last word:

So, I guess I just wait.

Turns out the problem was ongoing. At first I was able to send iCloud mail from the M1 MBA if I:

• Disabled iCloud Mail
• Rebooted the machine
• Enabled iCloud Mail

Eventually that kludge stopped working and I couldn't send iCloud email at all. I went through several layers of Apple Support. No one I spoke with had a clue.

I was eventually assigned to a senior support specialist. We spoke on the phone a couple of times and then continued via email. And, then, he ghosted me. No further communication. I sent a couple of follow-up messages, but never received a reply. I find this to be both disrespectful and unprofessional.

So, I proceeded on my own.

First try was to install the OS on an external SSD and set up a minimal account including my AppleID and iCloud info. I was able to send iCloud email from that account.

Then I used Migration Assistant to migrate the original account on the MBA boot drive to replace the minimal account on the external drive. I was not able to send iCloud email from that account.

So, I did what I always resist doing and have done only a few times since becoming a Mac user in 1984: Wipe the internal boot drive and reinstall the OS. This time I migrated from an account I have on my wife's M1 iMac.

That worked. Of course, it was a huge and continuing hassle. The account on the iMac was little used and had almost none of the work I had done on the M1 MBA. Fortunately, I have a recent Time Machine backup of the MBA so I am able to recover things like shell scripts, launchd plist files, etc.

I hesitate to call this a success. Wiping and reinstalling is more a surrender than a solution. It's a lot of work from which you learn nothing.

Oh, wait, I did learn something: Apple can't be relied on to solve difficult problems, even if you still have AppleCare.