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Thread: SBS 2008 outlook anywhere ssl certificates

  1. #1
    Join Date
    Apr 2010

    SBS 2008 outlook anywhere ssl certificates


    Please can anybody help. I am setting up a client with sbs 2008 and they have 3 users who need outlook anywhere access. I know you are supposed to get a 3rd party ssl certificate for this to work. The problem is we use a dyndns account for our ip as we don't have a static address. When you get an ssl cert they seem to do a whois on the domain name and this fails because ours is for example When you run the ssl certificate in sbs 2008 it creates When you try access the server with you get the certificate error saying it does not match. What happened to the selfssl from sbs 2003 and does this still work on sbs 2008. I don't mind adding the certificates manually to each machine as there are only 3 and no windows mobile machines at all. I need to get this working asap so any help will be apreciated.

  2. #2
    Join Date
    Jun 2009

    Re: SBS 2008 outlook anywhere ssl certificates

    The SBS 2008 self-signed SSL certificate that is installed in IIS 7 is a leaf certificate; meaning that the Issued to and Issued by names are not the same. Unlike SBS 2003, Certificate Services is installed as part of setup and a root Certificate Authority (CA) certificate is created to validate the server. If a client machine or mobile device trusts the SBS root CA certificate, it will trust any leaf certificate the CA issues. More information can be found here -

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