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I am forced to Jailbreak an iPad so that I can deploy a custom application for a client. This is an application that no one can have but him, so basically jailbreaking is the only choice I have?

I can't even install the app as a demo through the provisioning profile because that expires I think in 1 year?

What legal implications, in various jurisdictions, are there for jailbreaking an iOS device?

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You can use a provisioning profile as long as he gets a new provisioning profile before the current one expires.

Apple also has a business store (basically a corporate App Store) but I think that is way over the top for what you are trying to do.

The most legitimate/safe option is to deploy a provisioning file and update it each year…

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Seems like a valid option, unfortunately I don't think it would work. Given that some of the clients are overseas. –  Manuel Diaz Jul 29 '11 at 13:13
    
Provisioning files can be emailed. Distribution is the easy part. Remembering to send the file and keeping tabs on that stuff is the pain in the neck. –  Nate Bird Jul 29 '11 at 13:18
    
But doesn't the client have to compile the app into the iPad in order for the profile to go in? The clients basically will just have the iPad sitting there on a display. They won't have access to anything –  Manuel Diaz Jul 29 '11 at 13:22
    
I personally haven't let the provisioning profile expire using the same application so this is just my own understanding but I think that the app can just stay the same as long as the provisioning file for that developer is current. –  Nate Bird Jul 29 '11 at 14:01
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You also may want to check out testflightapp.com. We use it for testing but it may help manage the client app and provisioning better. –  Nate Bird Jul 29 '11 at 14:04
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