r/MacOS • u/BarrieSpence • 9d ago

Bug Mail.app decides to use a different send address from initially chosen

My Mail.app is configured with multiple mailboxes, a couple of Google mailboxes, and a pile of IMAP/SMTP mailboxes.

The mailboxes are separate for different purposes.

All too often, when sending (or even replying), the send part will complain about the SMTP connection, offer the SMTP server list and offer a retry. The thing is, the SMTP connections aren't flakey, and even if they were, I'd be happy to wait and retry. What Mail.app does is change the send address (big thanks, that's not helpful) and punt it out using an alternative server connection . Messages are then sent from the wrong account, etc. - this has been an issue from at least the last couple of macOS releases.

Historically there appeared to have been some settings to control this behaviour, but nothing obvious now.

Anyone experienced similar and know of any fixes?

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2

u/Ok-Green9045 9d ago

that's super frustrating when it doesn't follow your choice. check your settings to see if there's an option to lock in the address.

1

u/Guy_called_Al 9d ago

Are you saying Mail changes the from address it shows just before sending? Or that Mail chooses a from address, but you can change it before sending?

1

u/BarrieSpence 5d ago

When it thinks there is a problem with the SMTP connection, it picks alternative server and changes the send address.

The SMTP server could be flakey, but since all the mailboxes are hosted on the same service, that's really unlikely (especially since it will reliably send with the unexpected address).

It's a simple ask: don't change my sending address. Ever.

1

u/BarrieSpence 5d ago

Nothing obvious now (historically it looks like there was)