Posted by: kurtsh | October 13, 2012

HOWTO: Get rid of repeated Lync/Outlook authentication dialog boxes (A solution that worked for me)

UPDATE 10/14/12:
Since posting this write up, I seem to have gotten a fair amount of traffic from it telling me that it’s not just a MS phenomenon.  In the interests of helping everyone else, I wanted to post a couple things that have happened since.

    Some of the authentications came back.  I have no idea why.  After a while I began to think that some of the cached credentials that had been stored were no longer valid, nor were they being updated.

    So what I did was I went into:

    …and deleted every credential that looked related to Outlook or our corporate mail system.  Outlook simply re-requested the credentials when I opened it again, I made sure to check “Remember” or whatever it is that you check to keep the login credentials persistent for the next time my PC needed them, and things got better again.

    This is a weird one.  Looking at the Synchronization logs in Outlook/Exchange, (Outlook “Folder List” –> Sync Issues) I could see that several other people’s calendars were being synced to my machine. 

    This is of course useful when you need to be able to schedule things but if the users are on other Exchange systems, Exchange Online, Exchange Beta pilots, things can get hairy authentication wise apparently.  You can see in the screenshot to the right that I apparently am having permissions-based synchronization issues with numerous calendars. (Jose, Angie, & Ahmed in the above screenshot.)

    So I started to delete these cached calendars from my Outlook profile.  I went into Outlook and right mouse-clicked each calendar that I didn’t want to sync, and clicked “Remove Calendar”.

    I started looking at the local synchronization failures in Outlook “Folder List” –> Sync Issues –> “Conflicts”, and also “Local Failures” and started deleting mail objects that looked to be having issues synchronizing.  I also made sure to “Empty Deleted Items” to ensure they were “gone”.
    I forgot to mention this the first time but after changing settings in IE and clearing my credentials, I also closed out all instances of Outlook and Internet Explorer – i.e. restarted things.  None of these changes will work if you don’t close out the apps.


A week or so ago, I suddenly started getting and absolutely insane number of authentication dialogs from Lync, from Outlook, from Exchange… everywhere.  And for the life of me, I couldn’t figure out what the heck happened.

After all, my Active Directory login credentials when I first signed into my computer should be all that it needs.  I shouldn’t have to ‘sign in again’.

So I started doing some basic research on the matter.  After some very late night inspection, it turns out that a Security setting in Internet Explorer was mysteriously changed on my PC and I don’t know why.  The only thing I can think of is someone in our IT department pushed out a Group Policy object to my PC (and possibly others) & then later said, "oops" and removed object.  But if you know how GPOs work, this wouldn’t change Internet Explorer’s configuration BACK to the correct setting and they didn’t bother to set it back to the correct setting with another GPO… so I’ve been stuck with the wrong Security setting for a couple weeks.

So in case you folks ever get the same repeated “Windows Security” or “Outlook” authentication/login credential dialog boxes, here’s how I resolved it:

  1. Open Internet Explorer –> Tools –> Internet Options
  2. Click the Security tab.  Click the “Local Internet” icon.  Press the “Custom Level” button.  This will open a “Security Settings” dialog box with a list of settings..
  3. Scroll down to near the bottom of the list make sure there is check in front of "Automatic logon with current user name and password.”
    (This actually was already selected on my PC)
  4. Repeat this for “Trusted Sites” just as you did for “Local Internet”.
    (This is the setting that had been undone on my PC.  Note that if I go to Internet Options –>
    Trusted Sites and press the “SITES” button, I have our company’s Internet domain listed as a trusted site over https:.)

This got rid of all of my repeated authentication requests.


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