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iPhone VPN and DNS resolution issue

08/27/2008

During the addition of iPhones to our corporate environment, I was unfortunate enough to be pulled into aiding in troubleshooting issues we were having. Namely, the issue that we were unable to resolve anything within our "domain.local" zone once connected to the ASA via ipsec... Using the .local TLD is fairly common in the Windows Active Directory world.

After some head scratching, and a bunch of tcpdump sessions on respective interfaces (direct evidence was instant requests to multicast space), I finally stumbled upon some facts: Apple has an "Exception List" for every interface. Within this list, by default are 2 entries, "169.254/16" and "*.local". Bingo, THAT's why all *.local requests timed out and never hit a single dns server...

Not much of a solution, but using another top level domain with replicated records from the prior .local zone fixes this issue, and now everything within our VPN is reachable via hostname. *sigh*

As this stems from Bonjour, I believe the easiest fix will be to disable aforementioned service if at all possible.

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