Ever since I've installed Microsoft Office 365, Outlook has been a PITA. Literally, I'd get random popups saying my password is invalid, it'd keep prompting me if I click No... It's extremely annoying and I can't believe this.

The main issue that I have here is that Microsoft Outlook keeps telling me my password is invalid, and when I try entering it in again, it tells me it's invalid again. I've literally copied my password to the clipboard, logged into the OWA site (pasting the exact same password), and it works. Go over to Office, and it doesn't work.

Why does this keep breaking? What additional information do I need to provide here to get a valid solution? I'm so frustrated with Outlook for Mac. It's like it's half broken or something.

EDIT: Great... Now I'm locked out of my AD account. What in the freaking hell is up with Outlook? Does it just keep trying random passwords or something? How in the hell can I lock myself out by pasting the same valid password over and over that 100% works????