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Matt HodgeFlag for United States of America

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Outlook continuously asks for password

Hi - Have a strange issue with Outlook and have tried (i believe) everything, yet the problem persists. So we are using Outlook with hosted exchange. The issue is that randomly we get a pop-up asking for the password for the account...At first we added it and it was ok. Then it got to the point it was doing it every other day which became annoying. As soon as I added the password it would be fine, for a day or 2. This is what I've done so far:

1. Upgraded from Outlook 2010 to 2016
2. Created a new outlook profile
3. Went into the control panel/credential manager, remove credentials for the outlook account and added again.
4. Reset the email password

Of course, none of the above worked permanently. Anyone have any ideas what would cause this and how to fix it?
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REIT

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I've seen that popup when the password is correct but the connection to the server is not.  I discourage users from re-entering the password as there's no good reason it shouldn't be correct if it worked reliably before.  REIT has a good suggestion.
I'm wondering!!!??? Do you have to enter the password every time this happens or just by clicking on remember password and OK it will go away?

Are the users logon hours correct?, are the NIC going into sleep mode (Power Management).  Are you sure your licenses match your concurrent users?
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@hecgomrec - I've always entered the password (and checked the box to save it) it will go away, and mail will flow. but the next day, it could be asking for the password again.

There are no defined logon hours, they should be able to access anytime. NIC is not going into sleep mode. Licenses are for each user, and its a valid licensed hosted exchange account. FYI, there is another user on this same PC that has their own Windows login profile, that when she logs in and opens Outlook, she has none of these issues.
Here is something to verify!!

Try to compare settings (profile) for both users... and see if there is any difference.  This might be a long shot but your DNS are correct, specially your autodiscover.  I had an issue once where a server with 2 IP address will respond most of the time to its main but sometimes out of the blue will respond with the other one and had to force the IP in the host file.  

The logon hours are defined in your DC in the user account properties... all users most have.. do they have the same?