Outlook Anywhere Prompts for Credentials only for Outlook 2010, not Outlook 2013

I'm having a heck of a time with this one.  We have Exchange 2010 on premise, with our filtering through EOP.  Clients that are using Outlook 2010 Professional Plus are continuously getting prompted for credentials when off network and relying
on Outlook Anywhere.
I've read many threads about configuring credential manager appropriately for the internal domain and our external domain.  I can get them to authenticate just fine, and email flows, but they continue to be prompted everytime they connect again.
Here is the kicker:  When I install Outlook 2013 on the same computer, outlook anywhere functions just fine, no problems, no authentication prompt.
Like I said I have read a plethera of articles and threads about this, I have gone through all settings on Exchange, our edge server, our firewall, our certificate.  The MSSTD string matches our "Issued To" string.  NTLM authentication
is configured on both the client and the server.  Appropriate settings are configured on the firewalls. 
Anyone know why Outlook 2010 would have this problem, but not Outlook 2013 on the same computer, same user, same mailbox database?  
Thanks in advance!!!

I'd still Echo Ed's original question.
Do you have Outlook 2010 patched up?  At this time you need to be on SP1, and SP2 by October the 14th.
Also I expect you to have a recent update ontop of that as well.
http://blogs.technet.com/b/rmilne/archive/2014/04/14/office-2010-sp2_1320_-do-you-need-to-upgrade_3f00_.aspx
Cheers,
Rhoderick
Microsoft Senior Exchange PFE
Blog:
http://blogs.technet.com/rmilne 
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