SMTP Settings for iCloud Custom Email Domains
When self-hosting, applications like Mealie and Tautulli gain legitimacy by being able to email users for notification or signup purposes. Having iCloud as the backbone helps reduce the headache of hosting your own email server, though the documentation on utilizing SMTP is a bit lacking in certain areas. Here are some problems I've often seen or dealt with in my own experience:
- Make sure you are using an App Specific Password
These are generated from appleid.apple.com/account/manage

- Check which username you're using
In my case, I had updated my iCloud account to use the custom email address. This was not technically updating my AppleID account username, though. It's very confusing, but if you used to have a different username, try using that without making it an email address. For instance, if your Apple generated an email account for you called "[email protected]" you would try using "oldusername" instead

- Use STARTTLS if available
This would require you to use 587 as your port
Example
Username: oldusername
Password: fjse-mvxn-dwpl-qkut
Server: smtp.mail.me.com
Port: 587
Encryption: TLS/STARTTLS