Outlook 2016 doesn't accept password or app password

David/Gabriel,

First of all, I/we appreciate your efforts and help on this. I know you two are taking the brunt of the heat, and the thinking, of the lack of, is/are done by others behind the scene.

In a nutshell, I have a hard time believing the explanation given. I am having/had issues with multiple clients:

1. Latest GMail app for Android
2. Latest Outlook app for Android
3. Latest Outlook as a part of M365 (I added my account to my work Outlook, which is the latest build on the stable channel)
4. Older Outlook version you named

MFA is setup on all my critical accounts, including MS-based accounts. These clients are all very modern and support latest protocols, including OAuth. And if they don't work, I don't know what will.

The fact the issue is already happening to 1, 2 and 3, suggest the issue is tied to the account type and its lack of support for more advanced authentication process to your own liking, more so than the client issue alone. The data point and my personal experiences with this do not align with your assertions, so I don't think it's a matter of moving to a later version, i.e., Outlook 2021. It is possible that your team's constant tweaks of things in the last month created a fog of issues and made it impossible to pinpoint the behavior for us as users.

To your mitigation suggestions:

1. "New Outlook" that is being aggressively pushed right now, is a PWA (for those that don't know, it's like a fancy bookmark for browser website). Accessing non-MS accounts will basically allow Microsoft to be the proxy (for those that don't know, MS will become the middle man, accessing and storing your data from other non-MS platforms that you may have intentionally tried to separate). Microsoft's terms and conditions for the "New Outlook" indicate Microsoft will have rights to use those data. If Microsoft is under brute force attack as you suggested, WHY would any of us trust you to be the proxy of our other data?
2. If some of us are already having issue with the latest Outlook from M365, why would we migrate to Outlook 2021?

Hi, thanks for answering,

I actually installed the new free version of Outlook, it took me like 5 minutes to add all my 6 IMAP accounts, some from Gmail some from my web hosting provider some from msn.com and other from my ISP, Loved the auto-configuration, super easy and I actually like the software look.

Did some testing everything works great, I just needed to turn on the notification in my OS system settings to get the email notification banner to show up.

So the new Outlook is not that bad after all like someone complained here. Yes, you get the occasional ad email once in a while, and It just takes a click to send it in the garbage.

I guess that solves it for me.

Well, I came to conclusion what to do here (with outlook 2016) or an old mail programs/applications.

1. change to 2 steps authentication (verification) - outlook.com security options.
2. create an app password - outlook.com security options - copy your app password, and remember it.
3. at account setting delete old your ****@outlook.com account settings (outlook 2016)
4. at account setting add new account as ******@outlook.com. The password should be the password from app password.

Anyways, only way to work with old outlook apps (2010/2013/2016) for windows is using app passwords instead of regular passwords (2 steps verification).

I wonder how long this method of app passwords will work with gmail.com and/or outlook.com.

When this option of app passwords will stop working, we will have to change to an updated outlook program (2021), or work on outlook on the web. The problem with this, is that we will have also to update operating systems, because not everything is working with old OS such as windows 7 or windows XP.

Software companies, are forcing the users to advance, with upgrading OS and programs, otherwise, they will not be able to show profits.

I keep reading in these posts about OAuth and I haven't the foggiest idea what that is.

Hi David - I’m not as versed as others in this conversation so I’m hoping you can explain how a current paid M365 user, who’s been getting the password error messages in iOS installations, can fix the issue. In an iOS install email process, I have both a Microsoft Exchange option (which I’ve used for years) and an Outlook.com option which I’ve recently used to try to fix the password issue, and has been more stable. Is one better than the other in terms of security and/or password stability? Which option should I be using? Thanks.