Outlook 2016 doesn't accept password or app password

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

KR

Pierre

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)?

A few days ago, as one of my accounts stop receiving emails on my Outlook 2013. I deleted it thinking that it would be interesting to see if, by re-adding it, things might correct. Sadly, Outlook wouldn't allow me to re-add the account.

After reading your message I gave it another go just a while ago, repeatedly entering the password. However, in my case, I ticked the box to remember password and, hey presto - the account successfully re-added. Since then I've had no promptsfor my other three MS accounts.

This is such a wild issue and so random that one must conclude that something very disruptive has hit MS systems, accidentally or otherwise. And further disturbing is the fact that MS isn't coming clean about it.

Problem is, MS de facto depreciated outlooks 2013-2019. Not sure about 2021, but i am not in the mood for testing it out at my expense. I feel this all about pushing more AI into masses. Which is absent from non 365 Office. Can't think of any reason why having copilot in all other places is not enough. It tracks you in windows, it tracks you in Edge, it tracks you in all other places where you use MS services online. That and one drive integration which is also subscription/data mine for them. Google put utility to work around Outlook vs GMail limitations back in the days and i don't see why MS can't pull something similar. They did add utility to Outlook 2010 to work with modern protocols of MSN/Live/Hotmail etc. back in the days. So it's not impossible. It just don't bring them any money only customer appreciation and loyalty.

It's like this for almost 2 months.....