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Can you start jailbreaking straight away, or does it require an internet connection and Amazon account first during setup?
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Depends on the firmware of the device. Latest firmware (anything after version 5.18.5.01 - which released in October 2025) is currently not jailbreakable.

Jailbreak of any firmware after version 5.16.2.1.1 (June 2023) requires the Kindle to be connected and registered.

Anything prior to, and including this version, can be jailbroken with no registration.

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Don’t connect it. I bought one for this purpose and it updated to a version that didn’t have a known jailbreak
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I don't believe you need internet connection - IRRC jailbreaking steps were plug in the Kindle, drop the jailbreak folder into the root directory, then choose `Update` from the Settings screen.

The hardest part was finding the `Update` menu item. It's only visible if you go to Settings, then press the menu button again while on the Settings page.

Not sure if registering the Kindle was required.

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For the less reverse-engineering prone among us, there are also similarly sized e-ink displays that plug into Raspberry Pi DSI ports for maybe $5 more on Aliexpress. They might actually be salvaged kindle screens.
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Do you have a model number or link, please?
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I love it! Always fun to see the route somebody else took to get to the same end product.

Your post is making me want to try more Cloudflare Developer Platform stuff like Cloudflare Workers.

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