Problems with Autodiscover Outlook 2016


Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
We have spoken with almost every tech as MS and GoDaddy about this I think. So far no one has offered a working solution.
Two email accounts in our domain have constant issues with Outlook asking for their Password and not accepting what is entered. The same users can connect to their web portal using that password with no problem at the same time as it is being refused by desktop outlook. Tools such as MS's 'SARA' and the other MS "fixit's" have done nothing to resolve the issue.
The only fix that works for any period of time is to delete their account from the EAC, wait about 10 hours, then recreate the account with the same user name. This seemed to help but only for a few days during which time everything was perfect. After less than a week, the same issues were back.
There are close to 50 users on our Domain and none of the rest have a problem like this. We have contacted almost everyone I can think of with no one having any idea where the problem comes from or how to fix it.
I have often found some unique ideas on yoru forums and thought it would be a good place to look. This problem started back in the Fall of 2018 but until 2019 it was a sporadic issue. Since Jan it has grown to be a daily issue and the Users in question are the "CEO's" who do not want to use Web Portal Outlook and want a solution for Desktop.
The only place i can see a lot of difference in the connection is that Desktop required AutoDiscover while WebPortal access does not. We have noticed unusual activity in those files as well but this problem is Way over my head. I was hoping you could offer some new insights that no one has checked yet.
All the usual things have been tried: uninstall/reinstall Office, Generic credential clearing, etc.
This is the click-to-run version of Office 365 (x86) licensed from Godaddy and we are a Federated MS account if that helps.