(below details are copy-pasted from Microsoft forum)
Some of our users’ outlook stop sync with exchange and ask for password, as shown in below image:
But when we press the “Need Password” button, nothing happens. there is no prompt.
to fix the issue, I clear entries in Credential Manager, Delete Temporary Files, unchecked “Use Cached Exchange mode”, restart system and check this again.
POST 2: (Confirmed accepted answer)
There are a number of reasons for this. First I would look inside the Office 365 admin portal to make sure your password expiration policy is not set to only a few days
If this is ok, setting the below registry key to 1 in below path often resolves it
Key: DisableADALatopWAMOverride (DWORD)
This key may not exist, we need to create it.
February 14, 2022 at 2:32 pm
This also works https://docs.microsoft.com/en-us/outlook/troubleshoot/authentication/outlook-prompt-password-modern-authentication-enabled