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Auto-Discover issue with Split DNS

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  • Auto-Discover issue with Split DNS

    I recently introduced a single server Exchange 2010 SP3 RU1 into our organization and I'm having some auto-discover issues with mobile devices.

    Our internal URL for active sync points to
    Our external URL for active sync points to

    When you attempt to add an exchange account to a mobile client externally, it connects to our website http// which does not exist and the mobile client gets presented with a Plesk certificate. It never gets to the second https// which has a valid certificate.
    (Here is the output from the MRCA http//

    It prompts you to accept the self signed certificate from our webhost (PlesK) - even though there are no autodiscover settings configured there and it has nothing to do w/ our Exchange environment.
    • I do have any any SRV records set up for the autodiscover service.
    • I've already checked the make sure there are no wildcard DNS entries. (External DNS is hosted by a 3rd party)

    Autodiscover works fine internally. Any ideas?

  • #2
    Re: Auto-Discover issue with Split DNS

    It is because of the way that your web host is configured. They need to resolve it, so that the SSL certificate doesn't apply to your web site.

    This is a feature of Plesk, for Autodiscover to configure clients of the hosting company.

    Simon Butler
    Exchange MVP

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