Outlook Anywhere, Certificate

Posted on 2009-04-16
Last Modified: 2012-05-06
I have setup and enabled everything I know to implement Outlook Anywhere hosted on an Exchange 2003 server, SBS2003.  OWA works if I use http:// rather than https:    Both give certificate errors, however the login screen appears using http: on the address line of IE, upon pressing enter the http auto converts to https:

Everything appears to be good except the Certificate.  I have tested my connection using the following link,

It always fails on certificate.

I have everything set except for the certificate.  I am trying to generate a certificate on the server.

When generating the certificate do I use the FQDN of the server or the name of the MX record that points to my public IP for OWA?  Do I distribute the certifcate to clients first?


Question by:frdbadf
    LVL 9

    Expert Comment

    Follow these articles and you should be OK...

     You will use the registered name you use on the Internet not your internal domain...
    • i.e.

    LVL 9

    Accepted Solution

    Installing a cert using selfssl
    You can also use use a paid cert authority, such as Go Daddy (affordable), as must devices support these certs.
    LVL 65

    Assisted Solution

    Ideally you need to switch the certificate for a commercial certificate, and not use the self generated certificate. On the test site you can ignore the certificate trust issue if you wish, which may give you a better result.


    Author Closing Comment

    I ended up going to and purchasing a certifcate.  Smooth sailing thereafter.  OWA, although it worked before no longer generates certificate error.  Outlook Anywhere works as it should now.


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