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Outlook Anywhere - ISA 2006/ Exchange 2007

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  • Outlook Anywhere - ISA 2006/ Exchange 2007

    Hi there,

    I will describe my network layout before going into my problem.

    I have Exchange 2007 running on Server 2008. This box does all roles (Hub Transport, Client Access, Mailbox, and Unified Messaging).
    My DC is a Server 2003 box which is also my CA.
    Publishing OWA and Outlook Anywhere to the internet is an ISA 2006 box running on Server 2003.

    Now currently OWA works for all users.
    The problem I am running into is with Outlook Anywhere.

    After configuring it as to what I thought was correct, I was able to connect both internally and externally. But after a random time period, the connection to Outlook Anywhere will fail. This does not affect anything other than OA (OWA and mail services still work).

    To resolve this issue, I have to reboot my Exchange server.

    In the ISA alerts, I receive the following error:

    ISA Server was unable to establish an SSL connection with ******.********.local. A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.

    The failure is due to error: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.


    At the time of this error occurring, there are no errors showing on the other computers that would appear to coincide.


    Now I'm no ISA expert, but I believe the issue lies in the trust between my ISA and the Exchange box.

    Can someone point me in the right direction for how to test this relationship, or why it works for a random time period before failing??
    Has anyone out there encountered a similar problem?

    Please ask any questions if I need to clarify anything.

    Thank you in advance.

  • #2
    Re: Outlook Anywhere - ISA 2006/ Exchange 2007

    Is ISA server joined to the domain?
    How have you configured DNS on the ISA server?
    Have you reviewed the event viewer on both servers?
    Marcel
    Technical Consultant
    Netherlands
    http://www.phetios.com
    http://blog.nessus.nl

    MCITP(EA, SA), MCSA/E 2003:Security, CCNA, SNAF, DCUCI, CCSA/E/E+ (R60), VCP4/5, NCDA, NCIE - SAN, NCIE - BR, EMCPE
    "No matter how secure, there is always the human factor."

    "Enjoy life today, tomorrow may never come."
    "If you're going through hell, keep going. ~Winston Churchill"

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    • #3
      Re: Outlook Anywhere - ISA 2006/ Exchange 2007

      Originally posted by Dumber View Post
      Is ISA server joined to the domain?
      How have you configured DNS on the ISA server?
      Have you reviewed the event viewer on both servers?
      Yes, ISA is joined to the domain.

      What do you mean by configured?
      ISA can resolve Exchange as well as the DC box.

      I have reviewed the event viewer in all 3 computers.
      There are no log events that occur when the connectivity is lost.
      There are however several errors that I don't believe are related, but am looking into.

      One of them is below.

      Microsoft Exchange couldn't find a certificate that contains the domain name mail.********.com in the personal store on the local computer. Therefore, it is unable to support the STARTTLS SMTP verb for the connector Inbound with a FQDN parameter of mail.hemisphere-eng.com. If the connector's FQDN is not specified, the computer's FQDN is used. Verify the connector configuration and the installed certificates to make sure that there is a certificate with a domain name for that FQDN. If this certificate exists, run Enable-ExchangeCertificate -Services SMTP to make sure that the Microsoft Exchange Transport service has access to the certificate key.

      I am investigating this one as being a cause of the issue, but I don't see why. If it was a certificate issue, why would it connect one moment and not another?

      Thanks for your reply!

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