“It’s a rite of passage to run Tailscale on weird devices.”
So writes Mitanshu Sukhwani on his blog, detailing the steps for getting Tailscale onto a jailbroken Kindle. Getting there, and seeing a kindle entry with a satisfying green dot in your Tailscale admin console, takes some doing. But take the trip, and you’ll end up with an e-reader that can run some neat unofficial apps, and is more open to third-party and DRM-free ebooks. And with a Tailscale connection, it’s easier to connect to files and a command line on your underpowered little Linux slab.
“For me, it's the freedom of being able to do anything with the device I own,” Sukhwani writes by email. “What I can do with the freedom is a different story.”
A jailbroken Kindle allows you to set a custom screensaver inside KOReader—even transparent, if you like. Corporate logos are optional.
Jailbreaking refers to removing the software restrictions on a device put there by its maker. Getting around these restrictions, typically by gaining “root” or administrative access, allows for accessing operating system internals, running unapproved software, and generally doing more things than a manufacturer intended. With the Kindle, you still get the standard Kindle reading experience, including Amazon's store and the ability to send the Kindle books from apps like Libby. You just add many more options, too.
The term gained purchase after the first iPhone’s debut in mid-2007; since then, nearly every device with a restricted environment has gained its own jailbreaking scene, including Kindles (debuting five months after the iPhone).
Kindle jailbreaks come along every so often. Right now, an unlocking scheme based on Amazon’s own lockscreen ads, “AdBreak,” is available for all but the most up-to-date Kindles (earlier than firmware version 5.18.5.0.2). I know this because I wrote this paragraph and the next on my 11th-generation Kindle, using the open-source Textadept editor, a Bluetooth keyboard, and Tailscale to move this draft file around.
One paragraph doesn’t seem that impressive until you consider that on a standard Kindle, you cannot do any of that. Transferring files by SSH, or Taildrop, is certainly not allowed. And that’s in addition to other upgrades you can get by jailbreaking a Kindle, including the feature-rich, customizable e-reader KOReader, and lots of little apps available in repositories like KindleForge.
If your Kindle has been connected to Wi-Fi all this time (as of early December 2025), it may have automatically updated itself and no longer be ready for jailbreaking. If you think it still has a chance, immediately put it into airplane mode and follow along.
Obligatory notice here: You’re running a risk of bricking your device (having it become unresponsive and unrecoverable) and voiding your warranty when you do this. That having been noted, let's dig further.
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