Outlook 2016 doesn't accept password or app password

Hi Gabriel,

The timing of 23-24 Jan 2024 of this unresolved issue I feel is significant. Recent comment about region is also relevant. There must be a commonality with those experiencing the issue vice those not. Since it doesn't seem to hit major media tech sources it is not generating enough attention. Someone changed something, somewhere, possibly with alias or certificates. Changes could have been made outside of the Outlook team you access. If basic auth being deprecated, that means it's not completely disabled and shouldn't be affecting those paying for M365 intentionally. Pings and tracert responsive for 2-3 tested addresses for m.hotmail.com and m.outlook.com. Traces drop off at 13th hop, timeouts but concludes by hop 17. Of course not knowing what normal hop count and speed looked like before 23 Jan 2024. See certificate type error when IP address used vice m.hotmail.com

Also please, elevate this issue and ask a team other then the one your consulting. Let us know. Thanks

It feels to me like this is a regional issue somehow. I have two accounts set up using the Gmail app on Android. One of them seems to sync Ok for a certain period while the other isn't working. Then I maybe get some overlap where both work and then the other fails. Potentially something changes with GLB-type services? So maybe certain region MS data centres have the issue and certain others don't?

Both are using app passwords as the switch to modern Auth just fails to display a login page.

Since finding this thread, I've stopped trying to re-auth or use new app passwords and the accounts just sync for part of the day and then sit there saying sign-in required for the rest of the time. Frustrating to say the least.

Hello, been reading this thread daily. Those using M365/EAS, there is a supposed fixed resolution here 29 Feb. https://support.microsoft.com/en-us/office/outlook-desktop-exchange-activesync-connections-stopped-working-in-version-2401-da2dc0dd-297e-48ba-b6d9-ab18f5d522fc My hotmail (Microsoft email, outlook etc.) account has also been affected since (HST) 24 January on my Kindle Fire.  As a side note about 1-2 times a year for about 5+ years, email would get the authentication error that would last 2-3 days. Web outlook would be fine so confirmed never a password issue. My tablet is older, Fire HD 10, 7th gen, Fire OS 5.7.1.0 (8/23/2023) but works (99% of the time-got the authentication error twice, possibly more times since using spouse's tablet so may not have seen it, but error cleared on its own within couple minutes or follow prompt to enter via web my hotmail password) on a newer tablet Fire HD 10 Plus, 11th gen, Fire OS 7.3.2.9 (2/12/24). Will have to buy a computer because of this. I think there is more to this issue, since many have intermittent successful connections even if for short periods. Hope all those active on this thread will continue to comment, to get better definitive answers, because they should be able to specifically identify what actions led to the timing of this event.

From not the community crew:

Just found a difference which I don't know why they are different. Since my outlook 2021 and 3 of my personal free outlook.com address are all MSA* not the Bearer*. And it should be via Mapi over http. (Hold the control button and right click the outlook icon in the down right corner system tray.)

And it seems that if I add the ExcludeExplicitO365Endpoint in the registry, while add the account via the autodiscover in the mail(Micorosft outlook) classic layout in the control panel will be configured as imap account. (While adding the accounts via the modern layout seems did not affect.)

https://learn.microsoft.com/en-us/outlook/troubleshoot/profiles-and-accounts/unexpected-autodiscover-behavior
ExcludeExplicitO365Endpoint

https://techcommunity.microsoft.com/t5/exchange-team-blog/basic-auth-and-exchange-online-february-2020-update/bc-p/1205485
 ‘Bearer*’ means Modern Auth – ‘Clear*’ means Basic Auth.

https://learn.microsoft.com/en-us/outlook/troubleshoot/connectivity/description-of-the-connection-status-dialog-box
Authn

Indicates the authentication type that a given Outlook connection uses. Possible values include:

ERROR
CLEAR - (Outlook uses clear to indicate basic authentication - typically used together with SSL)
NTLM
NEGO
KERBEROS
ANONYMOUS
AUTOLOGON
.

This is a third party site.

• https://office-watch.com/2022/discover-mailbox-connection-details-outlook/
  The method of authentication used. Meaning how Outlook passes your credentials to the mailbox.

CLEAR  or Clear*- (meaning Basic Authentication which is being turned OFF for Microsoft hosted mailboxes and needs updating)

NTLM

For older Exchange Server connections we’ve seen CLEAR (NTLM)

NEGO

KERBEROS

ANONYMOUS

AUTOLOGON

Not documented by Microsoft properly but used with Microsoft hosted mailboxes are:

MSA* meaning MicroSoft Account login

Bearer* denotes Modern Authentication

In your haste to discredit others, you didn't read my posts. For several days now, I mentioned I tried to add my personal Hotmail account to my work laptops' Outlook, which is M365's latest desktop version from the stable channel. Both by description and the fact it's newer than Outlook 2021, you'd think it would work and it didn't... As for the MS people here, they were hyper-focused on IMAP only. Clearly, there is a disconnect. I can't tell if the new M365 Outlook is using EWS or Graph (but everything suggest Graph is still in development), it works fine for my work account but not for personal Hotmail in "Exchange" mode or "EWS" mode. I don't care if IMAP worked because I need calendar/contact sync, because IMAP is working for the current older client, so there would be no reason to upgrade.

I actually find it hard to digest that there are still folks left that do not care for contact or calendar sync. Perhaps they didn't know it was possible. Most people are clueless about authentication, email or calendar sync protocols. I run my personal life much like I do with work and I use calendar and contact list equally as I do with work. Most of data input are done on the desktop and I expect it auto-sync to the mobile clients in real-time.

I have been doing a lot of experiments in recent days. i can tell you the "New Outlook" is very very limited in its functionality. It will take a long time before they can replace the current desktop Outlook. I'd like to think folks that did spend the money on Outlook would have needs that a bit beyond very basic barebone experiences.