Outlook 2016 doesn't accept password or app password

Just received in one of my Hotmail accounts an ‘Action Needed – You may lose access to some of your third-party mail and calendar apps’ email which includes the link to https://support.microsoft.com/en-us/office/modern-authentication-methods-now-needed-to-continue-syncing-outlook-email-in-non-microsoft-email-apps-c5d65390-9676-4763-b41f-d7986499a90d admitting to the intermittent login issues. This should have been sent months ago. I wasted far too much time trying to figure out what has been causing the intermittent login failures until I discovered this thread. Very annoyed with Microsoft.

All you need to know:

Modern Authentication Methods now needed to continue syncing Outlook Email in non-Microsoft email apps https://support.microsoft.com/en-gb/office/modern-authentication-methods-now-needed-to-continue-syncing-outlook-email-in-non-microsoft-email-apps-c5d65390-9676-4763-b41f-d7986499a90d

Basic Authentication interim experience

Until September 16th, users signing into Outlook.com through Basic Authentication may experience recurring password prompts in Outlook and other third-party email applications. This is a known issue. After September 16th, users attempting to connect their Microsoft accounts through Basic Authentication will fail to do so.

The following versions of Outlook Desktop do not support Modern Authentication for Outlook.com:

Outlook 2007, Outlook 2010, Outlook 2013, Outlook 2016 MSI, Outlook 2019 LTSC. Any release of Outlook Desktop with a version less than 11601.10000 does not support Modern Authentication for Outlook.com.

No... 2013, 2016, 2019 and older versions do not support OAuth for free accounts such as Hotmail. OAuth is supported for business/enterprise accounts. This is by design to get you to pay upgrade to 2021 and upcoming 2024. This is at least what the MS folks are saying. However, I added my Hotmail account to latest Office 365 and it still had issues. Separately, you can use the "New Outlook" which is free but you will need to allow MS to access and take your data in exchange. "New Outlook" is very severely function limited...

Hi all,

I am using a Hotmail account with Outlook (desktop) Professional Plus 2016, with version (16.0.5450.1000) MSO (16.0.5452.1000).

Is my Outlook version the reason why I am getting the repeated password prompts? Or, is my application version okay for OAuth (in which case, I believe it should just be a matter of removing and then re-adding this email account to Outlook)?

TIA!

I posted before that even Outlook 365 desktop doesn't work reliably for Hotmail.com account despite of what they are saying. I was getting issues like this as well but in Outlook's error message. Windows, Office, Teams.... there is not one non-buggy software. MS keep adding bloatware and unwanted features into every product. All of us are Microsoft's QA because they no longer have structured QA of their own. I am in the process of moving everything off Windows and going to Linux, so if the access for Thunderbird is not fixed, I will probably need to drop even more stuff off Microsoft ecosystem. The ability to run a few Win32 legacy apps is not enough to constantly live with these issues and endless concerns about privacy.