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Select users constantly being asked for Exchange credentials on select computers

I'm starting to run out of ideas.  I have Exchange 2010 running on SBS 2011, just set up Exchange yesterday after exporting the PSTS from users exchange online accounts. I then deleted their mail profiles and created new ones for the on-premises exchange.

I have 5 Windows clients with Outlook 2013.
2 of them can connect to their exchange accounts no problem.
the others get Login Credential Spammed that autofills in their e-mail address and asks for their password, what's odd is that they can click cancel, then at the bottom of outlook where it says "Need a password" if they click that, it shows connected to exchange and they don't get spammed for a while.

Even more odd...   User A's outlook on Computer A is working great, User B on Computer B is getting spammed for login credentials.  When I tried logging into Computer A as User B, I was able to create an outlook profile and NO SPAM.  So then I try logging into computer B as User A and again NO SPAM.. So I can't narrow it down to user or computer! I'm about to cry lol,  Also, put User A back on Computer A, works fine, but User B back on Computer B is still having issue.  I've tried deleting their profiles again and same thing.

 For the record...

I have a UCC SSL Cert covering

SERVERNAME.domainname.local
autodiscover.domainname.com
SERVERNAME
owa.domainname.com
remote.domainname.com
and I have an "A HOST" set to my external IP and owa.domainname.com and autodiscover.domainname.com as CNAME aliases to "remote.domainname.com".   I have ports 25,80,443 forwarded to the server.


I installed SP3 update with no issues


I've enabled kernel authentication mode in ISS Virtual Directories "Autodiscover", "EWS", "RPC"

I've tried gpupdates, dns flushing, and restarts

I've also tried every kind of authentication method in Outlook with no change.  Changing the method on the Working outlooks did NOT break them!

Any ideas oh saviors of my sanity?
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matthewmalk248
Asked:
matthewmalk248
1 Solution
 
AbhishekJhaCommented:
Uncheck Always prompt for logon credentials in Outlook
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Glen KnightCommented:
This sounds like it's credential manager or cached credentials on the local windows user profile.

Login as another administrative user and delete the local windows user profile (or just rename it so that you can get any desktop shortcuts etc back if needed).

Then log back in as that user, creating a new local window profile and try and set Outlook up again.
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Simon Butler (Sembee)ConsultantCommented:
As this is SBS, was the server setup by the wizards? Did you configure the server via the wizards and then install the certificate through the wizards.

Repeating authentication prompts do not always mean there is an issue with the username and/or password, the most common issue is with the SSL certificate where the client cannot cope with the SSL prompt. If Exchange hasn't been configured correctly then things don't work quite right and you get prompts.

Simon.
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matthewmalk248Author Commented:
This is EXACTLY what the problem was Dematzer.  Thanks for reading the whole post and figuring it out! :)
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