How to Configure Windows SMTP Server to Support TLS Connection

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    I am new to certificates and I am running into a problem. We have been asked by some of our customers to implement TLS on our email communications.

    Our Setup:

    Server 1: Microsoft Server 2003 Enterprise (IIS 6)

    Role: SMTP Gateway/Mail Relay Server
    Spam Server (GFI Mailessentials)

    This server acts as a smart host to filter out spam and forward email to our Exchange Server.

    Server 2: Microsoft Server 2012 / Exchange 2010

    I have performed the Exchange Certificate on the Exchange Server. Purchased, installed the certificates and assigned the services.

    When I Telnet the localhost 25 on the Exchange Server, I am getting the 250-STARTTLS on the EHLO command. It seems everything is fine on the Exchange side.

    The SMTP Server is no giving this option.

    How do I get the SMTP Relay Server to negotiate TLS.

    Do I need to upgrade to a newer Server OS? Do I need to install certificates on the SMTP server? If so can I use the same certificates that I have purchased?

    Any help would be much appreciated


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