And to add to the pain i am a windows user just over to mac so I am having a heck of a time trying to find stuff The best way to fix any kind of technical issues on Mac, you can try. An email can also get stuck in the Outbox if it has a very large attachment. None of these solutions worked! Warning: Do not try moving them to ‘gmail outbox’. In the Mail app on your Mac, if the Send button is dimmed in the toolbar of your message, or your message can’t be sent using the outgoing mail server, try these suggestions Make sure the outgoing (SMTP) mail server is specified as directed by the. (This is different than using the 'Message -> Send again' feature. Archiving the email does not remove it, even if I delete the mail it takes a second and it just reappears. Somehow my Mac mail went back to the old irritating behavior. Also happening with a mix of email accounts, including some through Google and some on my own servers. Mac mail not sending stuck in outbox catalina ) It was never really broken - you just didn't fully understand that unsent messages will stay there until an opportunity to retry sending them occurs.