In reply to Bruno M Sales answer, I have a user who's O365 and Windows acct was receiving the password window blink and then disappear issue. I have also had other users in the past and some I could fix using the steps I took while others I have had to
re-image. Today was the first time, I used Bruno's answer and with some simple tweaks, had the Outlook Mailbox working correctly.
The steps I took on my own before the answer:
Cleared Credential manager of Web credentials and Windows credentials. Didn't work
Created new Outlook profile. Didn't work
Deleted the offline address book. Didn't work
Removed all Outlook addins. Didn't work
Ran repair on O365. Didn't work
Uninstalled and reinstalled O365. Didn't work
Flashed the BIOS. Didn't work
Cleared the Temp caches on the user's profile. Didn't work
Was able to successfully load Outlook 2016 in the Virtual OS on the same computer using the user's login account.
Used scan.pst to repair corrupted .psts' . Didn't work
Renamed the .ost the .nst . Didn't work
Went into Registry and renamed the user's profile. Tried to add the user to windows again however, it would not load the mailbox. Didn't work
Went into Registry and deleted the user's mailbox. However in the user's profile, it would not load the mailbox. Didn't work.
Verified prompt for credentials isn't checked in profile.
Closed all Microsoft applications from running in the background, tried to load mailbox only. Didn't work.
Ran MS Support and Recovery assistant for O365. Didn't work
Uninstalled Windows Security updates for February 2019 to include Adobe Flash updates and Security update KB4485449. kb4485449 would not uninstall and this was the time that this issue also began. Didn't work
Using Bruno Sales answer Create a new registry value:
Go to the registry editor (Win+R; regedit)
go to HKEY_CURRENT_USER -> Software -> Microsoft ->Office -> 16.0 ->Common -> Identity
Inside "Identity", create a new REG_DWORD value called "EnableADAL" and leave the value at 0
Restart the PC and try again to login from Office 2016.
A couple of tweaks after:
I also uninstalled O365 first then added the registry value, rebooted, then installed O365.
You have to log the user's account into Word and now the password field is on the same page as the email log in but it works.
You have to create a New Outlook profile and the password prompt is the small sub window style but it works.
Thank you Sir!