Mail app on macOS repeatedly asks for SMTP

Question

Level 1

10 points

Mail app on macOS repeatedly asks for SMTP

Latest MacOS, M4 Mac mini.

I have my own domain managed by Apple since 2022 and all has been working great. I also use "Hide My Email" pretty extensively with no issues.

Recently (past 2-3weeks) some times I reply to a message that has an HME address, it asks for the outgoing SMTP server to use. I always use iCloud and select the option to "always use this server". This is the only SMTP server that I have had configured for a long time (years). Yet each time it asks again what server to use. This is getting annoying.

Posted on Dec 9, 2025 7:31 AM

Reply

Answer 1

Top-ranking reply

azaksalmarzur28

Level 4

1,098 points

Dec 11, 2025 12:02 AM in response to jzcxr

Rebuild the Mail SMTP server mapping (works for most users)

Open Mail
Settings → Accounts
Select your iCloud Mail account
Click Server Settings
Under Outgoing Mail Server (SMTP), choose
iCloud Mail (smtp.mail.me.com) manually
Now click Edit SMTP Server List
Delete any duplicates or old entries
Quit Mail completely
Reopen Mail

This forces Mail to write a new identity map for Hide My Email addresses.

Reply

Answer 2

jzcxr Author

Level 1

10 points

Dec 11, 2025 9:20 AM in response to azaksalmarzur28

I just did this and there were no SMTP servers in the list at all. I clicked save and the iCloud server was removed from my account. I reselected iCloud in server in the server settings dropdown and hopefully that will force the rewrite.

I'll give an update in a few days when I have a chance to test it out.

Thanks

Reply