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SBS 2008 and Exchange 2007 SSL Certificate

Discussion in 'Software' started by madman045, Jan 29, 2009.

  1. madman045

    madman045 Kilobyte Poster Premium Member

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    This is probably one for Sparky, but im at a loss

    Just setup our SBS 2008 Standard server and purchased a SSL certificate for remote.domain.com

    Now SBS has already got its own self signed certificate installed and ive added the new one using the wizard.

    Now when I check the list of certificates in Exchange, it shows both of them


    Do I need to remove the self signed one?

    When we try to use Outlook remotely, our old server was 2003 server with 2003 exchange and self signed certficate and it automatically connected


    Now when we open Outlook, every time it asks us for our username and password details, is there anyway to get it to how it was before?

    Also when connecting to it via the OWA url, it's coming up with check the certificate, so its as if its not seeing the remote certificate


    Any suggestions?

    Its also been suggested I change the certificate to a multi domain one, so instead of just remote.domain.com it has


    mail.domain.com
    remote.domain.com
    autodiscover.domain.com
    server.local
    server


    would this be the best route?

    I've also thought of adding mobile.domain.com for future mobile devices, would this be a good idea?

    Also does anyone know if SBS wizard adds the certificate to IIS?

    And final question, how do you generate a multi entry code for generating the certificate with a 3rd party SSL certificate company?


    Thanks

    Andy
     
    Certifications: 70-270, 70-290, PRINCE2 Foundation, VCA-DCV & VCA-DT
    WIP: MCSA 2008, VCP5-DCV, ITIL V3
  2. Sparky
    Highly Decorated Member Award

    Sparky Zettabyte Poster Moderator

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    When you open up OWA what is the certificate error? It is something like the root certificate authority is not trusted or something like that.
     
    Certifications: MSc MCSE MCSA:M MCSA:S MCITP:EA MCTS(x5) Security+ Network+ A+
    WIP: Exchange 2007\2010
  3. madman045

    madman045 Kilobyte Poster Premium Member

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    It's ok, we have just got to get used to doing everything through remote.domain.com now, however it wont go down too well with clients...

    Just need to figure out this multiple entry SSL certificate so i can get all the other sub entries added to make life easier.
     
    Certifications: 70-270, 70-290, PRINCE2 Foundation, VCA-DCV & VCA-DT
    WIP: MCSA 2008, VCP5-DCV, ITIL V3
  4. beatrice

    beatrice New Member

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    Hi madman

    sounds like the certificate didnt take right.

    Be sure to follow the steps from the vendor to install the cert into the store. Often you will have to place a cert also into the intermediate store as well.
    Once you have done that, you should run the Add trusted Certficate wizard and then select the cert you installed from the list. The wizard will bind the cert to the SBS sites in IIS.

    In IIS you can check by selecting the server node (eg. Server 01) and then scroll down the middle pane and click on server certificates. The list will show you which certificate is bound to what site.

    cheers
     
  5. madman045

    madman045 Kilobyte Poster Premium Member

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    Thanks for the pointers beatrice, will have a look

    I naively assumed the SBS wizard did its job correctly when I told it to add the new certificate.

    Andy
     
    Certifications: 70-270, 70-290, PRINCE2 Foundation, VCA-DCV & VCA-DT
    WIP: MCSA 2008, VCP5-DCV, ITIL V3

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