Outlook 2016 doesn't accept password or app password

I know, its kind of an odd behaviour, but I think most complains comes from users on Outlook 2013, 2016 and other "not supported" clients. MS argument is "if it doesn't support OAuth it will not work". Also they just started rolling out this implementation so something somewhere maybe got broken, some user experience issues some don't who knows, this is the MS way, throwing things at the wall until it sticks lol.

I got super tired of having to enter my password, I bought the bullet and installed the "new Outlook" just for fun and I don't know what to say, I was surprised too, but I like it lol. It works for me personally, I eventually told myself that if I didn't like it I will have installed Supernova but I didn't.

I know that installing the new Outlook is not feasible or desiderable for everyone depending of the situation, in my case was a simple matter of adding a bunch of various personal email accounts.

More complex scenarios will require some investment for the cost of upgrading your email software, if a free solutions is not an options.

I don't think that MS just planned to set-up us with the purpose of pushing to upgrade our software, of course that will benefits financially but they also really want to catch-up with what other companies already did as security is concerned. Off course there will be some causalities along the road but its a sacrifice they are apparently willing to make :)

At the end of the day I think we we all benefits from having a more secure access to our emails, and I don't have to see that ******** password prompt ever, it gave me PTSD.

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?

It has to be a bug in some fashion because...
Even their newest available product has the issue.

I mean unless the intention is to do away with that product, but i cannot see that being intended?
I mean that would kind of shoot the MS Office thing right in the foot, Outlook and Excel are probably the two heaviest used products in that suite., so i have to think that something is not quite as planned?

On amusing side note, if you put in a product ticket, you may well be told that you can find information on this issue here, in this thread.
I mean, the response is not wrong, it just doesn't fix anything.

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

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.

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.