Outlook 2016 doesn't accept password or app password

You right my account is pretty new, I never had the need to join a MS forum until now,

I can usually solve pretty much all technical issue by myself, that's why I get paid for, and no so much to waste time in a forum, let aside 14 years.

You must have a lot of time on your hands, or needed quite a lot of help apparently or both.

You do realize, this is basically where everyone from technet and msdn etc have landed into these conjoined forums as various things have ceased over time.

I'm looking at this from techcommunity area
everything kind of bleeds together now

Same for me. Was stable the entire day. Now throwing errors every minute.

Gabriel, please provide some info on what's going on behind the scenes. Is work actively being conducted to resolve this? Could that be the cause of these moments of successful connectivity?

Please...help us understand if MS is working on a fix or if we should be looking at alternatives to Outlook.com accounts?

Thanks!

Gmail API regarding OAuth for the 3 common protocols, including POP3.

OAuth 2.0 Mechanism  |  Gmail  |  Google for Developers

Again, I truly believe you are mixing up a bunch of things because we don't fully grasp which each means. OAuth/OAuth2 is an authentication method. IMAP/POP3 are email protocols. One does not replace another. IMAP/POP3/SMTP traffic are already encrypted. What is being updated is the initial authentication method, such that tokens are used instead of repeatedly sending credentials. That's A-Okay fine. What we are saying is that for Exchange/EAS, even if we upgrade to a client that supports OAuth/OAuth2, we are having the prompt issue or can't even setup the account. This suggest the consumer email accounts like Hotmail/MSN/Live and so on do not support OAuth-based Exchange/EAS. If this is the issue, then upgrading the client will not solve the problem. Upgrading the client will allow you to access via IMAP but that's not what we are after as most of us can have IMAP working now. And if I am reading everyone right, most people are after sync of contacts and calendar as well.

Let me break it out even more:

Exchange/EWS is used by desktop apps and EAS is used by mobile devices. Microsoft's publications indicate both support OAuth. Both are sync methods that support email/contact/calendar. MS indicate they are ending Basic Auth. In theory, all we need to do is delete the current account profile and re-add using OAuth. The thinking is new Outlook clients, such as Outlook 2021 will support OAuth. What I am saying is that even though the client support it, our issues seem to suggest server is rejecting OAuth for these account types or that they are not provisioned to support OAuth. If latter is true, then MS needs to make that very clear because it means we will lose such support for 3rd-party clients. On the flip side, EWS is not due to completely end until 10/2026 - that's a long time in tech world, so I rather have it working for the next 2 years, until Graph-based client support become available. If MS ignores all of this that there will be no contact/calendar sync until we use Outlook for Android/iOS app, then it will trigger people to re-strategize, such as moving their email/contact/calendar off MS and let it all go to iCloud or Google. These decisions will have an impact.

Seems like this is going into place too early?

I have the trial of O365 outlook here
and has same issue.

doesn't matter if provided real or app password, it repeatedly asks for it.

Seems a bit odd to put this into place before there is a product that can do it properly?

Sadly i just realized, the "new outlook"
Yea cannot legally use it, it lacks required supported features.

I don't mean in a general sense, in a general sense obvious one can use it.

But not for anything that has legal requirements where there are certs, encryption etc
Sent a sealed envelope as a test, just shows as a blank email
Bummer :(

Maybe they could at least update the current O365 outlook desktop client.
It obviously "should" work, but something must be a little off.

Look I get it, what I'm saying is that if you want to vent your frustration and discuss about technologies is ok.

What I'm saying is that no amount o complaining or hitting on the MS people here will change the direction that MS has decided to take, they will not release a patch or an update for Outlook, this is not a bug its a "new feature" right?

And like you said, yes, you will need to adapt, and find out what will be now the best technology to use for you as an user or for your business moving forward.

Good luck