Exchange 2007 hosted problem

Posted on 2011-05-11
Last Modified: 2012-05-11
Hello everyone..

I have an odd issue,  I host exchange services for a couple of small businesses.  Everything has been working fine - even the address book isolation has been working (an article I had followed previously found here on EE - a little complicated, but it works).  Anyhow, here's my problem.  First consider this:

** The microsoft exchange connectivity tester says my installation passes with no errors.

So, what's happened is this..  I host exchange for a domain.  We'll call it  My exchange server is setup with a certificate.  We'll call that URL  I've setup the DNS so that a SRV record points the _autodiscover to  It's been working fine, until the certificate for expired.  Now outlook says that is expired or invalid, even though the web URL that outlook uses to connect has nothing to do with  The SRV record points to, and it works.  They are just dismissing the cert warning now and still receiving email, but this is annoying.

Autodiscover tests and connectivity tests using MS's exchange connectivity tester PASS.  What's going on here?  Why is outlook checking the cert on instead of just being happy with my perfectly good cert on

Thanks, and prompt solutions are very much appreciated!

 - Tim
Question by:TimFarren
    LVL 2

    Accepted Solution

    I seem to have solved my own problem, although I still don't understand what was making this particular issue tick.  To resolve the issue, I conctacted HostMonster who hosts our web content (not our exchange server solution, WEB only) and asked them to remove the certificate which had expired from  After they did this, outlook quit complaining about it.  We didn't need a certificate on that site anyway.  On my end, my certificate is still good, and I'm hosting their exchange, AND the domain name referenced in the exchange setup is DIFFERENT than their email domain.  This scenario is what has me confused to begin with.  I have no idea why outlook 2007 was trying to test the validity of a certificate which isn't even referenced anywhere in the setup apart from the fact that it matches their email domain name.

    To clarify.. their email domain is
    My exchange server, which has a valid cert, is  (examples only) has an SRV record which points _autodiscover to

    Autodiscover had been working perfectly, mail connects and works.. just.. why did it care about the certificate for their mail domain?  And further, once the certificate was removed - why didn't it care anymore?  I'd call this a bug.  Anyone?
    LVL 32

    Expert Comment

    since you are hosting the client is going to attempt to connect to autodiscover using the smtp domain name, say the address is
    the client is going to attempt to connect to first
    if that connection fails it will attempt
    if that connection fails it will attempt an SRV lookup for and use that result

    one of those other attempts must have worked before the SRV lookup
    LVL 2

    Author Closing Comment

    Found the answer myself.
    LVL 2

    Author Comment


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