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If this all is about a hypothetical case, it is a quite hypothetical one. There just isn't much that could break by doing a jailbreak (despite the name). It's basically a works-or-doesn't issue. In fact, if we were to indulge into theoretical matters that never actually occurred, there might be some point in the middle where an undiscovered kernel issue in the FAT32 driver happens to eat all your kindle's data triggered by an unfortunate cooperation of the jailbreak, some bit-toggling by sun eruptions and a flaky power source - well, you're borked :-) Not entirely true, but it really is so jailbreak-independent that it would really depend on the symptoms on how to approach the issue.
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