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Truthfully, Amazon could be much more aggressive with book DRM. See how often Apple pushes out updates to stop jailbreaking. Amazon could similarly be aggressive on DRM on new books with constant upgrades. My belief is that they see DRM as necessary to secure the acceptance of publishers, and that they do update occasionally, but that they aren't as aggressive as they could be.
I suspect they will have a similar attitude about jail breaking. They won't go out of there way to encourage it. New software updates will not attempt to make old jailbreaks backwards compatible. But you won't see weekly anti-jailbreak patches.
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