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Issues with Autodiscover and UCC SSL cert

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Issues with Autodiscover and UCC SSL cert - 3.Jan.2012 3:26:22 AM

damadhatter

Posts: 10
Joined: 29.May2008
Status: offline

So here is some background on my setup. SBS 2011 (so running Exchange 2010) I purchased a UCC cert from GoDaddy and made my CSR for the following names.

remote.mydomain.com
autodiscover.mydomain.com

I made an A record for autodiscover.mydomain.com which points to my SBS WAN IP

I have used TestExchangeConnectivity.com and everything passes with no issues

This SBS box is in a colo so I would never really be accessing it from the LAN, it would all be WAN access.

I am trying to setup my Outlook 2010 client and having some issues

#1 Autodiscover takes a long time 3-5mins, any way I could figure out what is going on?
#2 Once autodiscover works I get a message saying "an encrypted connection to your mail server is not available"

I have been looking around but unable to really find anything relating to my exact setup. Any help?

If I go to autodiscover.mydomain.com I am redirected to https://autodiscover.mydomain.com and I see the IIS7 page

If I go to remote.mydomain.com.owa I am redirected to Outlook Web Access which has no issues.