Outlook 2016 doesn't accept password or app password

Every cloud hosting provider has major issues being used for spam. Azure, AWS, GCP, even Cloudflare. It is a game of whack-a-mole for them, knock one down, another pops up.

However as far as the very simple spammers who just open a free account with something like gmail, outlook, etc, I see far more from gmail than from outlook. Gmail users I know also receive far more than anyone I know using outlook, which may be related to Google's TOS basically allowing them to use and sell your information however they please.

You've really said this already, but it's not my experience as far as spam origin. Now I am repeating myself. :)

Anyway, we are happy with our move to Gmail, and will not be returning to Microsoft for this service largely (but not exclusively) as a result of this authentication issue over the past 2 weeks.

Cheers.

This thread is not about Google or Microsoft but the issue with authentication servers. And it is not working.

Your comment is very limited in scope and ignore obvious facts. There is no such thing as "free" product. In this case, we paid Microsoft through the Windows OS license that is part of the device cost - it's not free. The Outlook clients, that we are having issues with, is also a paid product - it's not free. Hotmail/MSN Mail/Outlook mail is a free product but they use it to mine data in our emails and place ads. It's also not free, just paid differently.

If Microsoft does not want to make sure these run smoothly, i.e., I get 5-10 or so email on my personal account, versus 100-300+ a day on my work account, then Microsoft can exit the consumer market. Email is now becoming a critical part of our daily lives, it need to have certain level of care and reliability. I am not expecting 99.99999999999% up time for consumer products, but an issue of this severity and impact, effecting multiple email clients including Microsoft's own, lasting almost 2 weeks, is somehow OK to you is just mind-blowing...

Not OK to me at all. But also not surprising.

Properly configured outlook clients have not had this issue at all. 2FA with modern auth (Oauth2) has not been impacted, at least not widespread, for exchange connected accounts (including personal outlook.com accounts using Outlook client).

They have been warning that legacy passwords and even app passwords are being phased out. However that was not supposed to have happened yet (not app passwords anyway) so somebody botched something, probably tested their changes against modern auth and ignored the other methods.

Anyone having issues with Outlook client needs to enable 2FA on their account and update their client to use Modern Authentication with native exchange (MAPI/HTTPS) connectivity.