Outlook 2016 doesn't accept password or app password

I’ve now been watching these notification emails coming in for about 2 months and meanwhile the functionality in my Outlook 2013 client has fluctuated wildly.

I currently have 3 (three) Outlook.com accounts and 1 (one) Hotmail.com account installed in my OL2013 client.
Formerly, I had several basic Outlook365 email accounts associated with my domains also installed.
I forget exactly when it happened, but I believe sometime on 2021 or 2022 all those accounts stopped working.
GoDaddy sent me a link to a page containing instructions on how to make them work.
I had to add 1 or 2 reg. keys and values for each.
The result was a scripted dialog box would open (one time) into which I would apply the password for each of the accounts, and, as if by magic, they (the OL265 accounts) worked.  No further prompts by the dialog box appeared.  Add the reg. keys, put the password in the new dialog box, and shazam.

I never did have any problem with any of my proper Outlook.com or Hotmail.com accounts.
That is, until January of 2024.

The first sign of trouble was on my Hotmail account.
Soon followed by my primary Outlook.com account.
As an aside, GoDaddy charges a small fortune for their basic Outlook 365 accounts so I dropped them like a hot potato.

But I still have my Outlook and Hotmail accounts.
Over the next couple of months, the accounts impacted by this specific issue have been entirely random.
Sometimes one (or more accounts) will prompt for password and which account(s) they may be are unpredictable.
Lately I even noticed I usually don’t even need to actually enter the password in the dialog box for the accounts to actually work.
I have just click the “X” or “Cancel” and Outlook connected to Exchange as it normally would.
Then somedays I have zero issues.
Ironically, the account with which I first discovered the issue, my Hotmail account, has reliably been the most stable of the four accounts.

Today, one of my Outlook accounts was HORRIBLE so I thought I’d remove and reinstall the account to see if that might resolve the issue.
During the “Add Account” process I was prompted a bazillion times for password before it would add the account.
Finally I removed the check on “Remember password” and clicked cancel and IT WORKED!!!!
PLUS, I restarted Outlook 2013 SEVERAL times and it never prompted me once for a password.
This is weird because for the previous two days, all 4 accounts worked fine.
I was beginning to think perhaps the issue was resolved.
But no…

Numerous times I’ve noticed all I need to do is click “Needs password” on the Outlook status bar and it connects WITHOUT me needing to enter a password.

I can’t imagine how MSFT can allow this issue to persist absent some super-secret plan to forcibly deprecate older versions of Outlook.

Is there something I’m missing?

Previously I sent my email address to you (when you asked for them) but no one has ever contacted me to perform testing.

Is there some other steps I’m supposed to be taking (other than the steps I previously had to take for my old Outlook 265 accounts)?

Hi Gummo Marx ... It worked with 2016 ... no idea about 2013 ... sorry ...

KR

Pierre

Do you know if 2021 will import Outlook 2013:

• Mail rules which I regularly back up into a .rwz file?
• Data files which update automatically into a .pst file?

Hello everyone, 💕

It's me who created this thread back in January (01/24/2024).

I have now given up on my Office 2016 Plus installation. Unfortunately!

I have bought Office 2021 Plus ... quite cheaply. I have removed Office 2016 from my wife's PC (she is now a tester 🤢) and installed Office 2021 on her PC.

The good thing was that even if you uninstall Office 2013 Plus, your Windows 11 remembers EVERYTHING. That means codes, e-mails, databases (OST or PST) and usernames etc.

But ALWAYS make a copy!!!

She has no password pup-up's now 👍😎

Will test for 1 week - and the it is my turn to upgrade.

Best of luck to all of you.

Best regards,

Pierre Damgaard Rømer

The problem with OAuth2 is that is does not work over EWS for Personal accounts. So, older email clients (like mine) that have used EWS to connect for years and that were assured EWS would continue to work, are not able to connect anymore. While adding OAuth2 support is trivial for an email client that already supports it for Business accounts, replacing EWS is longer-term project.