Mac Mail (Version 16.0) Woes

This on a 15" M2 MBA running Sonoma 14.2.1 and Mail Version 16.0.

Two problems:

  • Sometimes Mail fails to send iCloud mail because it is unable to connect to the iCloud SMTP server. According to Connection Doctor this is a TLS Failure to Authenticate error. I actually started having this error on an M1 MBA over six months ago. I have raised the issue with Apple Support and have dealt with two senior support people, but neither seems to have a clue. The only clue I have is that the error only seems to happen when Mail attempts to use Port 25 (not encrypted) to connect to the SMTP server instead of the preferred (and encrypted) Port 587. When I look at the configuration in Mail it seems to default to Port 587 , so I have no idea why it attempts to use Port 25.

    The only cure for this silly problem is to turn off iCloud Mail, reboot the machine and then turn iCloud Mail back on. Surely there’s an easier way.

  • The other problem is that Mail sometimes fails to get new mail when it wakes up. Even if I hit Get Mail, nothing happens. According to Connection Doctor, the connection to the IMAP server has succeeded. The only solution I’ve found is to quit and restart Mail after which it does fetch new mail. (Isn’t IMAP supposed to be PUSH?)

Anyone have any suggestions on either of these problems?

On Feb 20, Retsima reported, regarding Mail.app running under Sonoma 14.2.1 on a 15" M2 MBAir:

"Mail sometimes fails to get new mail when it wakes up. Even if I hit Get Mail, nothing happens. According to Connection Doctor, the connection to the IMAP server has succeeded. The only solution I’ve found is to quit and restart Mail after which it does fetch new mail. (Isn’t IMAP supposed to be PUSH?).

I have observed this problem daily for at least a week now, with Mail.app v16.0 running under macOS Sonoma 14.3.1 in my MacBook Pro 16-inch, 2019; and also in my wife’s MacBook Air Retina, 13-inch, 2020. FWIW, both Macs have Intel processors. This problem affects all three of my e-mail accounts and both of my wife’s, with three different IMAP servers and one Exchange server.

In particular:

• Mail.app more often than not fails to get new mail when my/her Mac wakes up from Sleep. For hours or a day after the Mac wakes up, Mail.app receives no message. Meanwhile, the iOS Mail app in each of our iPhones downloads messages normally.

• Hitting the "Get Mail” button/icon has no effect.

• The only solution we’ve found is to quit and restart Mail.

• Yes, IMAP is supposed to be “PUSH.” So is Exchange.

Three days ago I searched Apple’s Support website; then I tried Google; but I could find no report of the problem. Then, since my MBP16 was still covered by AppleCare, I reported the problem to Apple Support by telephone. The person to whom I spoke was polite and said she’d asked her supervisor about the problem; but, she said, the problem was news to them and they knew nothing about it.

Chuck
TidBITS subscriber since 2011

I sent you a message including my Apple Support case number. Next time you communicate with them you might mention that case number to demonstrate that the problem has been previously reported.