How can I detect if a phone has been jailbroken remotely?

Question

I manage multiple iPhones at my organization using Active Sync settings in Exchange 2007 as well as the iPhone Configuration Utility. I've recently performed tests where I concluded that if I were to obtain a user's phone (ie they lost it), I would be able to access much of the information on the phone without their password by jailbreaking it to gain root access and retrieving .db files from the phone.

I'm looking for a mechanism for detecting a phone has been jailbroken and automatically wiping or notifying us when it occurrs. Note that this is for AFTER we've alreay pushed the configuration profile to the phone, NOT during initial configuration.

Answer 1

I think this is more of a development issue than administrative--perhaps there's an admin tool for this, but I'm not aware of it.

I do know that Apple inserted a jailbreak test in its iBooks app: when launched, the app would try to run some unsigned code (which should only work on a jailbroken iPhone). If the code ran, the phone was regarded as jailbroken, and iBooks would refuse to run. This was quickly defeated by the next version of jailbreaking software, which I believe circumvented that test.

Obviously this requires the user to do something in order to trigger the test (i.e., launch iBooks). It might be possible to get around that requirement with local notifications or push notifications (caveat: I am not a programmer).