When I email a certain person I always want my outgoing email to be on my email account X rather than account Y. For example, I always want to send Bob email messages via Google Gmail rather than Yahoo Mail.

Is there a way in Mail.app for macOS Mojave to enforce this rule, so I use the right email account for that particular recipient?

  • Mail > Preferences > Composing; Addressing - Send message from: and select Select Account of selected mailbox to reply using the same account used to receive the email from Bob (presumably to your Gmail address). Newer macos should have 'Automatically selected best account'. – user90735 Mar 25 at 6:59
  • From the left pane, Mailboxes -> Inbox select the provider first. Then, when clicking to Compose messages it starts with the selected provider in "From" field of your mail. – Yoan Mar 25 at 14:23
  • Mail.app doesn't support automatic sender email address selection based on recipient. I guess it could be somehow solved with an Automator service, but it would be cumbersome at best. As a workaround, you could set Mail > Preferences > Composing; Addressing - Send message from: to Select Account of selected mailbox, as explained by user90735 above, and have multiple Viewer Windows open, each one for one of your email addresses. You could then select the appropriate Viewer Window before composing a message. – jaume Apr 17 at 7:29

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