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I think that this happens if you change the send-with account for a given account (so if account X sends via the Y server, it will have Y's return address). Other than that, I've never had the return address for a reply have anything other than the address of the account it was sent to.



Regardless of the server you set Apple mail still sends the email as from the account you hit reply on.

However some servers will rewrite the mail serverside to match the authentication user to prevent spam. The main service I know that does this is gmail (and probably any of the “big” mail providers). If you send through a more basic typical Linux server it will send as the “correct” address.

Although these days it’s mostly a bad idea to do that because you’ll hit issues with SPF, DKIM, etc.

The main actual issue you have here is if you manually hit “new message” then you need to think about which sender to choose if you’re coming from a unified inbox view instead of the specific inbox for the account you want to send from.


> Regardless of the server you set Apple mail still sends the email as from the account you hit reply on.

Unless you flip the setting to always send it from one address.


It happens quite often. It somehow decides to pick up outgoing email address based on to field. It’s annoying. There is a setting for it but it appears to reset with every update.

The only solution I found so far is to have distinct footers for each account and ALWAYS look st the footer and from.

It’s a dumb default.




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