Upgrading mail database stuck after upgrade to Monterey. Restarted twice, progress bar still doesn't move.
I have not seen this trouble widely reported. the best way to get the problem fixed in the long term would be to report it to Apple. https://www.apple.com/feedback/
I have another idea though. Open Mail and go to the menu bar. choose Window>Connection Doctor. Are your account(s) connected properly?
Also try deleting the message that won't send. It will likely be in your Outbox if this problem is superficial. It may come back up in On My Mac>Recovered Messages. Delete it there too. THEN try sending it all over again.
Try force quitting Mail(hit Command+Option+esc, select Mail and click Force Quit), signing out and back in, turning wifi off and on.
I just upgraded and have the same issue. None of my emails have been sent in the last two days...didnt realize that until an important email didn't reach my contact. UGH!! need this fixed NOW
Did it and it DOES NOT HELP ME.
Mail upgrade stuck
