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Opening Exchange Outlook anywhere using the standard setup using domain remote.xxx.co.uk

Posted on 2014-12-19
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Last Modified: 2015-01-29
One of our clients has Outlook Anywhere setup on an external device such as a laptop, this connects and works successfully. The issue is that every time the client connects, a certificate error pops up. We have been searching the clients SBS 2008 server to locate the certificate which is appearing with the error message. I have also attempted to locate the certificate via the exchange powershell and typing get-exchangecertificate. The certificate that is appearing with the error message is not listed once the command is entered in on powershell.

Any advice would be greatly appreciated.
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Question by:CDSFIX
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5 Comments
 
LVL 13

Expert Comment

by:Norm Dickinson
ID: 40509019
You may need a certificate that is issued from a certificate authority such as GoDaddy.com. The self-issued certificates are of limited use in these environments.
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Simon Butler (Sembee) earned 1500 total points
ID: 40509084
When you get the certificate prompt, you need to open the certificate and see where it is coming from.
I expect it is related to the web host.

A lot of the web hosting packages will have Autodiscover on them, using the URLS https://example.com/Autodiscover/Autodiscover.xml (note the lack of remote or Autodiscover at the start of the URL).
Outlook queries Autodiscover every time it starts. You cannot stop that behaviour. If the above is happening, you need to get the web host to turn it off, so that Autodiscover works correctly.

If you only have a single name trusted SSL certificate on the server, then you will also need to configure SRV records for Autodiscover, which also means you need to ensure that there is no wildcard on the domain.

Simon.
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Expert Comment

by:Robert_Turner
ID: 40512569
Simon is right, the issue is going to be external to that of your SBS server.  The key point as you have already stated is that "The certificate that is appearing with the error is not listed", meaning outlook is talking to something else.
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LVL 1

Expert Comment

by:hassan afzal
ID: 40574765
do the directory address match the cert, internal and external?
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