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Peter BittingerPeter Bittinger 

Outlook 2010 and Mobile user password prompts for Office 365

We have Office 2010, with Exchange on Office 365 federated to Okta.  Also we have AD with delegated authentication.  We have recurring issues where some users will get prompted for their credentials in outlook desktop client.  This issue comes and goes - it will prompt for 2 hours, then stop, then happen again 2 days later.  The same issue happens on their mobile device at the same time.  I have open cases with both Microsoft Tech support, and Okta tech support, both think it is the other vendor's issue.
Very frustrating for the users that are experiencing this...  Has anyone else seen these issues?  Any ideas on the resolution?  I saw there was a suggestion for Office 2013 registry key, but Office 2010 does not have that key.
ThomasThomas (Okta, Inc.) 
Okta support has been working on this issue, and is testing a possible solution.  We will report more results as the testing is completed, soon.

Thomas Hill, Support Community Mgr, Okta
Arturo HinojosaArturo Hinojosa (Okta, Inc.)
Hey Peter,

My hunch is you have rougue devices locking your users out, then a timed "auto-unlock" of accounts setup that is unlocking the account to let them back in temporarly. During the time the account is locked out, that is when you are seeing the EAS profile error messages in Outlook and their mobile device. Can you check your system logs and see if there any unrecognized login attempts on the account?

If that ends up being the cause, I encourge you to check out Okta Mobility Management (OMM). Our product integrates your AD with user mobile devices in a way that whenever users udpate to reset their AD password, OMM automatically updates the EAS profile password on all their enrolled devices. This prevents lock outs and removes the burden on end users to remember to update all their devices.

If you want to learn more join our "Ask me Anything" session on 10/15 at 10 AM PT. I will be hosting an open Q&A on Okta Mobility Management, Adaptive MFA, and other topics. You can learn more here: bit.ly/1joCz1Q
Scott HolmScott Holm
We are seeing the same issue Peter. After our swap to use AD as our master and matching the immutable id, all of our office 2010 users cannot connect, we do not see any auth attempt to Okta made by these users either.