A weird thing happened to me relating to this. So I had my kindle break, got customer service to send me a new kindle and then 10 months later fixed the old kindle. Apparently the kindle had stayed in non-working condition and had not updated making it jailbreakable. My main kindle is the newer one as I don't want to touch my books with a jailbreak or anything. So I basically got 1 extra kindle for free.
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