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Can't connect to Outlook Anywhere

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  • Can't connect to Outlook Anywhere

    So I have an Exchange 2007 box (all roles on a single box, fresh install), a DC and an Forefront TMG; On the DC I installed the CA, and on F-TMG I published OWA and it's working great (off course I've imported the root certificate on the external client witch is not part of the domain); For the second step I tried publish Outlook Anywhere and it failed; I've read allot of tutorials over the internet and looks like none it's working for me.
    I thought it's something with the TMG rule so I replaced TMG with an RRAS server and did a simple port forwarding, OWA works great but not Outlook Anywhere (The connection to Microsoft Exchange is not available. Outlook must be online or connected to complete this action); so it's definitely form Exchange, but I kan't figure out what it is.

  • #2
    Re: Can't connect to Outlook Anywhere

    Run it through the Microsoft test site with a test account at
    That should flag some of the errors for you.
    Simon Butler
    Exchange MVP

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    • #3
      Re: Can't connect to Outlook Anywhere

      ignore Forefront for now.

      concentrate on getting the Outlook Anywhere configuration working INSIDE the domain, then you can focus on publishing it correctly externally
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      • #4
        Re: Can't connect to Outlook Anywhere

        well I done that for a couple of times and failed at the RPC over HTTP test saying that "Testing of this potential Autodiscover URL failed.", and I have some certificate errors, but does are expected since I have an internal CA certificate. Now something that made me curious, I took the AutoDiscovery test (skiped the certificate test) and everything was ok, even the autodiscovery url was retrieved from IIS, so how come on the RPC test failed ?
        I don't think it's an autodiscovery or authorization problem since outlook passes that and fails at the logon step.

        I attached a screenshot with the error
        Attached Files
        Last edited by adispy; 2nd February 2011, 22:03.


        • #5
          Re: Can't connect to Outlook Anywhere

          just buy a godaddy certificate. they are like 50$
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          • #6
            Re: Can't connect to Outlook Anywhere

            I'm in a test environment, so for now I'm ok with the internal CA, and I don't see any problem since I import the root ca to the external client; I even deployed an OCSP server and it's working great, well except for the Exchange part
            Outlook Anywhere it's working on the internal network, no problems here...

            So looks like I'm having this trouble only if I install all role servers on a single box; if I install the CAS server on another box, Outlook Anywhere & Autodiscovery it's working greate
            ok I got this working, I had to edit the host file on the Exchange server providing the fqdn and netbios name of the exchange server; It's all working good now

            Thanks for your help
            Last edited by adispy; 5th February 2011, 13:07.