One time, when I had to use outlook, someone called me asking why I wasn't replying to emails since like 3 days. Turned out Outlook had decided I could receive emails, but when I was replying, the email would put in a special folder "to be sent" or something, because the MS outgoing server was not working. I looked like a fucking imbecile when I figured it out and tried to explain what happened.

[–] blackbirdbiryani@lemmy.world 1 points 1 year ago

Another fucking stupid outlook thing is that you can only schedule send emails from the Web client, not the desktop app. If you try to do it on the desktop app it sits locally in your outbox and only sends if the PC holding the email is on. And if it's off when the scheduled time passes, the email just sits in the outbox. So incredibly stupid.