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Re:Software Jailbreak for Any Kindle by Semaphor on Saturday April 30, 2022 @11:16PM (#31221860)
You can manage your collection with Calibre (and at least used to auto-strip DRM in the process) without jailbreaking, I did that with the Kindle Keyboard many years ago.

The only thing I remember about jailbreaking, was being able to use custom screensavers and fonts.

Re:Software Jailbreak for Any Kindle by QuikAccount on Saturday April 30, 2022 @11:28PM (#31221935)
I don't think you can strip DRM any more. At least I can't with my Kindle Paperwhite and Calibre.
Re:Software Jailbreak for Any Kindle by joecool1029 on Sunday May 01, 2022 @12:32AM (#31222208)
You can still, but unless the libraries needed to do it are updated you'd need to use the last version of Calibre built on python2.
Re:Software Jailbreak for Any Kindle by risho on Sunday May 01, 2022 @01:31AM (#31222465)
I didn't have any issues removing drm from my purchased amazon books as of a few months ago using the latest version of calibre released at the time and the latest version of the kindle for windows app.