Outlook Security Alert when Starting

Posted on 2011-05-03
Last Modified: 2012-06-27

I just installed Microsoft Small Business Server 2011 with Exchange 2010. Then, I setup a Windows 7 workstatioan with Outlook 2010. So far, things are going well. The only thing that bugs me is that each time I start Outlook or OWA I get a "Security Alert" message, and that there is a problem with the site's security certificate.

I don't want to purchase a security certificate for this server since it is a test server. Is there a way to get rid of these Security Alerts? If so, how?

Question by:jhieb
    LVL 3

    Accepted Solution

    You have to install the self signed Exchange certificate to your client so that it trusts it and doesn't prompt with the warning.
    LVL 16

    Expert Comment

    by:Viral Rathod
    To install certificate :
    In Windows Internet Explorer 7, click Continue to this website (not recommended).
             A red Address Bar and a certificate warning appear.

    Click Certificate Error button to open the information window.
    Click View Certificates > click Install Certificate.
    Click Yes, to install the certificate, when warning message appear
    LVL 56

    Expert Comment

    by:Cliff Galiher
    viralrathod: That doesn't work as SBS 2011 uses a CA and the root will not be trusted.

    To the op: Knowing what specifically the error says would be helpful in solving the issue. You may need to vew the details to get this information. One of two usual possibilities exist:

    The first is a trust issue, which you'll need to resolve by either joining the machine to the domain or by installing the certificate package. SBS creates this for you and can be downloaded and installed from the RWA page.

    The second is a name mismatch and can be fixed by ensuring your external DNS records are created properly and  that you've run the Internet Address Wizard to create the proper certificate name and internal DNS records.

    It takes all of this working in concert for SBS 2011 to work as expected.

    LVL 1

    Author Comment

    Most likely you are correct. Do you have a technote for installing a self signed certificate in SBS 2011? I guess I can Google it. If you have some easy references with pictures/examples then please let me know. Thanks.
    LVL 56

    Assisted Solution

    by:Cliff Galiher
    The internally signed leaf certificate AND a client install package is created when you run the Internet Address Wizard from the SBS console.


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