Outlook Anywhere Security Certificate Issue
Hi All, I have recently taken on a sbs2008 domain to look after and administer as the company was unhappy with the previous administrator. They would like to get Outlook Anywhere working as they work off the domain quite a bit and don't really like using OWA. I have spent 3 days trying to get this working and have now hit a wall. The issue is with their Security certificate as when the server was set up they had a dynamic DNS address installed ( xxxxxxxxxxxxxx.dyndns.biz ) which is a free one. This allows access to the OWA, RDP and RWW fine but gets rejected when trying to connect with OA as the proxy server's certificate details are different to dyndns address. In a bid to get round this I have used the IP address of the server in the Connect Using HTTP properties (remote.xxx.xxx.xxx.xxx ) but this doesnt work either. How can I get round this?. Would changing the servers web address solve this? Any help greatly appreciatted. PS - VPN connection to the server works perfectly for Outlook, its just the pesky Outllok Anywhere!. Joe.
November 6th, 2011 5:34pm

What does the tester say is the problem? : https://www.testexchangeconnectivity.com/
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November 7th, 2011 11:14am

You can't mix a host name and IP address in the URL, so remote.12.123.123.123 is never going to work. SBS is very picky with SSL certificates. Do they have a static IP address? Do they have their own domain? If so, then switch to a commercial SSL certificate. I have instructions here: http://exchange.sembee.info/2007/install/multiplenamessl.asp I have instructions for SBS 2008 here: http://exchange.sembee.info/2007/install/sbs2008ssl.asp Setup the server using the wizard and the names it wants to use (so remote.example.com) and then everything will drop in to place. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.
November 7th, 2011 12:54pm

Hi Guys, Thank you for your replies and help here. As you may have guessed I am a little new to this so your wisdom is very much appreciated. Sembee:- 1. Yes they have a static IP 2. Yes they have their own domain 3. Will work through the links as posted. 4. What sort of cost is involved with getting a commercial certificate? Thanks Joe.
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November 7th, 2011 6:01pm

$60/year from http://certificatesforexchange.com/ You need a unified communications certficate, aka multiple domain, aka SAN (subject alternative name). That is NOT a wildcard certificate. Therefore as they have their own domain, setup remote.example.com and autodiscover.example.com to point to their static address. Then get the SSL certificate as per my instructions. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.
November 7th, 2011 7:05pm

Hi Joe, Any updates? Similar post, please see: Outlook Anywhere - External Host name question http://social.technet.microsoft.com/Forums/en/exchangesvrclients/thread/721467c8-8467-4fc6-a270-e163bd17f6d1 Frank Wang
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November 9th, 2011 1:44am

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