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Auto-Discover issue with Split DNS

Home Forums Messaging Software Exchange 2007 / 2010 / 2013 Auto-Discover issue with Split DNS

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    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?

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