Outlook 2016 doesn't accept password or app password

"You keep saying "new Outlook" or email client is not relevant to this issue"

Yes I do, this thread is about, as the title said "Outlook 2016 doesn't accept password or app password" and not about the new free Outlook client which you are trying to get your unrelated concern answered here, how's that you don't get it, are you purposely doing this? You are just hijacking this thread with a new issue, this is call sliding or hijacking a thread with the intention of sliding the topic from the current issue to a new one.

How your concern for the new Outlook client, as you put it using "ads masqueraded as email", and for other "privacy issue" has to do with this topic,?

Your concern is about the "new Outlook client" (which you apparently are even using) or whatever you want to call it, it's not related to the issue that users in this thread are experiencing and discussing, which once again is related to authentication and not about the new Outlook client, ads, privacy, scraping or its feature limitations.

Just because a mod here mentioned it "as a temporary workaround" to use the "free" new native Outlook doesn't mean that we are or want to discuss this topic, which apparently you are the only one that is concerned with.

So if that is the case, what is stopping you to open a new thread regarding whatever your concerns are about the new Outlook client?

Is anyone moderating this topic?

I don't mean to disrespect or downplay other issue, but in regard if that is true or not, is a complete new topic that can be discussed into another thread by whom my be interested.

Please let's try to focus on this issue and and not slide the thread.

Thanks

You keep saying "new Outlook" or email client is not relevant to this issue BUT IT IS. We are all having an issue with password prompt and it has been suggested to use "new Outlook" because it supports OAuth "better" than Office 2013/2016//2019. Therefore, concerns with "new Outlook" as a solution needs to be discussed. Three main concerns people have are: 1) it shows ads masqueraded as emails; 2) Ts&Cs indicate MS servers will access/scrape all your data including non-Microsoft accounts; 3) it has limited protocol support that may not meet the needs of most people using Outlook. People use Outlook because they have multiple email accounts and/or need different access protocols. Otherwise, they would stick with free "Mail" instead of going with paid Outlook desktop apps. I would argue email client is particularly important to this issue.

It is very relevant because Microsoft themselves, as I referenced, are the ones suggesting the use of "New Outlook" as a way of avoiding this authentication issue, but there are several of us here going back to page 13 with privacy and security concerns (notably with regards to non-MS e-mail accounts) in regards to how "New Outlook" works (very differently as a proxy) from traditional e-mail clients as per its terms and conditions such that it is not a viable option for us. Hope you understand. Cheers.

This is not resolved, I'm using the MSI version of Outlook 2016 with my Hotmail setup as Microsoft Exchange, with an App password and 2 factor authentication is enable. Every couple of days it authenticates and lets me read my new emails in Outlook but most of the time I get a prompt for my password which keeps returning.

Microsoft, are you doing this deliberately to make us take out a Office 365 subscriptions, if so then at least tell everyone rather than pretending to resolve the issue.

Issue not resolved - more updates on my experience.

1. I wrapped up my international business trip and flew back to the US. After landing in the US, my phone immediately went into the password prompt loop. Everytime the phone prompts, it get a notification tone and it was a pain while waiting to pass through Custom with the phone beeping. It's the first time the phone seen T-Mobile 5G network in more than 2 weeks. It lasted over 1.5 hour and it's only when I am half-way home on a drive when the password prompt went away on its own.
2. On my home computer, I didn't get any prompt initially and 2 weeks of emails were downloaded into desktop Outlook app (from Office, not Window's new Outlook PWA). Then about 2 hours later, desktop Outlook 2013 started the password prompt look. I have modern auth enabled through regkey. My work computer Office 365 with latest updates also went into the password prompt loop.

This issue is FAR from being resolved. Prior to 1/23/2024, I almost never had this level of password prompts. At most when MS is messing with their infrastructure, I get a couple of hours of this issue once in a long long time....definitely not 2+ weeks like this time.