Outlook 2016 doesn't accept password or app password

It's not my place to judge my friend's girlfriend or their relationship. I know plenty of very busy people live their lives through Outlook/calendar, so I can relate to my friend. I work 14 to 18 hour days, travel constantly, so I, too, live off my calendar... If this is an one-off issue, perhaps she should be more forgiving. However, you are forgetting this has lasted 4 weeks now! What mission-critical infrastructure in our lives would have down-time this long? Imagine your internet feed at home, or your mobile phone, or your electricity service go on and off throughout the day for 4 weeks... Let's see if you miss a meeting or two, 4 weeks in a row, and see how that fare for you at your job.

I mean as far as your friend is concerned, that's kind of absurd, and if that was truly the only reason the relationship ended, that's someone you don't want to be involved with anyway. Do they not have phones to call each other? Text messages? Email is far from guaranteed delivery, we take for granted that it is reliable but stuff sometimes goes wrong, gets sent to spam (or blocked before even hitting your mailbox), etc. I think he dodged a bullet honestly.

I've missed work and client meetings due to email issues (on their end or on ours), nobody got fired.

I totally agree! What keeps me in the Windows ecosystem is 1) Outlook and that fact I have decades of emails, calendar and so on all saved and backed up in PST; 2) MS gave into the Chinese government and is fully functional in China for my business trips there. Aside from Outlook, there is really nothing keeping me invested in this ecosystem.

This issue have real-world impact. My friend was dumped by his girlfriend over this... because she sent him an invite for a group meet up but it never arrived into his phone's calendar. He either missed it or couldn't find the place without the invite...and she felt disrespected. It would not surprise me if people are dealing with miscommunication issue and conflicts as a result of this problem.

It almost like promo event for subscription-based Microsoft 365.

Very bad one. Maybe they are routing for MS Edge/Web access, but i have issue with web Outlook too. Some links don't work.

Jokes aside i feel your pain and frustration. I can't be productive without outlook and sinking it down is not the smart move on MS side. There is not much of journalism outcry on the subject though. Which surprises me.

I have work provided Office 365 pro and there outlook has it's own unique issues which bug me as well. Again, one of the most needed tools in office is not up to the task.

I tried and it did not worked. It also was intermittent. Worked for one and did not for the other and now first is out too.