Both my wife (M1 iMac and M3 MBA) and I (M1 and M2 MBA) continue to have baffling issues with iCloud Mail.
Me: On both of my Apple Silicon machines Mail insists on using Port 25 for TLS Authentication with the iCloud SMTP server. This almost always fails:
Oddly, if I turn on my VPN then Mail switches to the correct Port 587 and authentication succeeds:
What's going on there?
If I look at Mail>Settings>Accounts>Server Settings:
![Screenshot 2024-05-04 at 4.56.00 PM.png]( "Screenshot 2024-05-04 at 4.56.00 PM.png")
All four of my email accounts show up.
But, if I look at Edit SMTP Server List:
![Screenshot 2024-05-04 at 4.56.20 PM.png]( "Screenshot 2024-05-04 at 4.56.20 PM.png")
Only two accounts show up. Where did Gmail and iCloud Mail go?
My Wife: Now and then on her M1 iMac all of her iCloud mail accounts disappear from the "From" line on outgoing email. So, to send mail from iCloud you have to manually re-enter all of the iCloud mail addresses. This is nuts.
Oddly, these errors (?) only show up on the Apple Silicon machines. No Mail problem with iPhones, iPads, a very old Intel MBA and an equally old Intel iMac.
I previously tried to deal with the TLS authentication error with Apple Support. It was a massive waste of time. I ended up talking to three different senior support people. None of them had a clue and all of them ended up refusing to respond to email. I gave up with Apple Support. (And, yes, I did submit a bug report. And, I had previously submitted Connection Doctor logs, Capture Data logs and a Screen Recording. I never heard back on any of this.)
It's very frustrating.
Me: On both of my Apple Silicon machines Mail insists on using Port 25 for TLS Authentication with the iCloud SMTP server. This almost always fails:
Code:
READ May 04 15:26:39.106 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:p56-smtp.mail.me.com -- port:25 -- socket:0x6000014f1440 -- thread:0x600002e0f440
501 5.0.0 AUTH abortedOddly, if I turn on my VPN then Mail switches to the correct Port 587 and authentication succeeds:
Code:
READ May 04 15:42:58.114 [kCFStreamSocketSecurityLevelTLSv1_2] -- host:p56-smtp.mail.me.com -- port:587 -- socket:0x60000143a880 -- thread:0x600002f899c0
235 2.7.0 Authentication successfulWhat's going on there?
If I look at Mail>Settings>Accounts>Server Settings:
All four of my email accounts show up.
But, if I look at Edit SMTP Server List:
Only two accounts show up. Where did Gmail and iCloud Mail go?
My Wife: Now and then on her M1 iMac all of her iCloud mail accounts disappear from the "From" line on outgoing email. So, to send mail from iCloud you have to manually re-enter all of the iCloud mail addresses. This is nuts.
Oddly, these errors (?) only show up on the Apple Silicon machines. No Mail problem with iPhones, iPads, a very old Intel MBA and an equally old Intel iMac.
I previously tried to deal with the TLS authentication error with Apple Support. It was a massive waste of time. I ended up talking to three different senior support people. None of them had a clue and all of them ended up refusing to respond to email. I gave up with Apple Support. (And, yes, I did submit a bug report. And, I had previously submitted Connection Doctor logs, Capture Data logs and a Screen Recording. I never heard back on any of this.)
It's very frustrating.