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Can't Get Outlook Working with Integrated Authentication

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We are not able to get integrated Windows auth working for our on-prem Exchange 2013 deployment.  Our setup is pretty straightforward;

  • Single Mailbox server (cc-exch-01)
  • Single CAS server (cc-exchcas-01)
  • AD Domain: clarityinternal.net
  • Public DNS Domain: claritycon.com

For Outlook Anywhere, I have the same settings on both the Mailbox and CAS Servers:

  • Internal URL: cc-exchcas-01.clarityinternal.net
  • External URL: exchange.claritycon.com (resolves to the internal IP of the CAS server)
  • Authentication: Negotiate

The certificate on the CAS server is issued by Entrust and has:

  • Subnect Name: exchange.claritycon.com
  • Subject Alternate Name: cc-exchcas-01.clarityinternal.net

When users launch Outlook from a domain joined PC, they are prompted for credentials and I can't figure out why.

jon


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