Outlook 2016 doesn't accept password or app password

Well, our company let Microsoft fully manage it, so there you have it. Microsoft can't even manage their own stuff.

I work in high-tech... like really high-tech industry. NOT every company can afford to staff half-dozen support specialists or analysts just to baby-sit all of Microsoft's ill-advised approach to many things. Even our highly skilled IT people are getting sick of all the issues.

We live in a really sick world controlled by Microsoft now, even for someone like me that work in high-tech for almost 30 years and embraced every new thing. Every 2nd Tuesday of the month, we get the lovely Patch Tuesday nightmare from Microsoft. After 2-3 weeks of back and forth, the issue may get resolved and be only in time for the next round of Patch Tuesday nightmare. On top of that, we get the lovely monthly update to Office suite and the weekly updates to Edge. Overall, I find myself constantly dealing with Microsoft bugs and I am a developer so I can't image how non-tech people deal with these endless of issues. I don't know how we have time left to focus on real work.

Life used to have 2 certain things, tax and death. Now, it's tax, death and endless of Microsoft bugs.

Well, you're having the opposite experience I have with outlook both for personal and for work. Possibly an implementation issue by the IT department.

When done properly in a corporate environment, you will never be prompted for a password, not even every 365 days, since it is tied to your windows login.

From my experience Gmail is one of the worst offenders with spam, I'm constantly helping friends with gmail accounts write complex filters to try and get some of it. The vast majority of spam I get in my own accounts comes from a gmail address via google servers.

The company I work for is using Office 365 for Business. I have a supplier/partner account with one of my customers that is on Google Workspace. The amount of issues on Office 365 is so alarming that I am talking to our IT about switching. Google's stuff just humming along with zero issue. So much so, I sometimes send myself a test email to see if the account connection is still alive - and it is.

With Office 365, if it's not password prompt, it's that stupid 2FA/MFA prompt that has a "...don't ask again for 365 days..." box. Even checked, I get the prompt at random well before 365-days is reached, even before this current issue. These are critical accounts, so I have very secured randomly generated passwords and I don't have the password manager on my phone, so every time I get 2FA challenged out of normal, I can't address it until I am back near my computer. If it's not password issue, it's sync issue. My calendar and contacts are not auto-sync'ed, even though the setting is set to auto-sync. Again, no issue on Google. The moment I add a calendar or contact, it's on my phone within a few seconds. With Office 365 and working EAS connection, I have to manually go to the account setting and force it to sync to get updates.

I travel constantly for work and Google challenges me the same way I expect it should - when I go to far and random places that I never go to. With Microsoft, it's so stupid that it's beyond words - always challenge me at my foreign office, or the same hotel I've stayed at for years, both of which has fixed IP addresses. When I go to some random places where I think it highly risky, MS doesn't challenge me.

If you also look at spams, vast vast majority of them are transmitted on Microsoft infrastructure from Russia and East European spammers. Microsoft seems to have no way to stop them effectively. Ironically, I have gotten a lot less Microsoft-originated spams on my non-MS accounts from since this current issue. At least there is one little benefit out of this whole mess - spammers probably have a harder time to send spams.

exactly. im with outlook 2019. password prompts were becoming less frequent in the last two days, I thought maybe MS was having it fixed. Boy, was I wrong! I started getting prompts couple times an hour today again!!!

The mobile network vs wifi is a timing thing. Each time you connect, you get a random server at MS. Some are working fine, some are not. So if you toggle your wifi again, that time it might work fine on wifi, but not on mobile network.

They aren't blocking IPs so far as I can tell (except when you try too many times in a short period, it does seem to block it for a little while), it is just based on the server you get assigned by DNS randomly.