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Mail.app outgoing mail problem when the from account is also the Apple ID for the active iCloud account

As the title suggests.

For example:

  • You have signed into iCloud with your Apple ID johndoe@gmail.com (you want to use your address johndoe@icloud.com, which is under this account)
  • You also set up the Google/Gmail account johndoe@gmail.com in Mail.app
  • You compose a new email, intending to send it from your johndoe@gmail.com Google account
  • johndoe@gmail.com is selected as the 'From' account, so you think everything is fine
  • The message fails to send. Mail.app tells you it failed to send because the iCloud(!) SMTP server rejected the email. Of course it did. Mail.app asked it to send an email as johndoe@gmail.com.
  • You check the Outgoing Mail account for johndoe@gmail.com (the Google account) which was already correctly set to Google so you are not sure why Mail is trying to send the email with the iCloud SMTP server.
  • What is presumably happening is that Mail.app is interpreting the johndoe@gmail.com you have selected as the 'From' account as the Apple ID johndoe@gmail.com and therefore trying to send with the iCloud SMTP server.
  • The workaround is to go into Accounts > iCloud > Account Information > Email Address, add your @icloud.com address, and remove the johndoe@gmail.com address which is tripping up Mail.app
  • The fix would be for Mail.app to produce a warning message when such a conflict was encountered.