Let's put Tailscale on a jailbroken Kindle

(tailscale.com)

139 points | by Quizzical4230 4 hours ago ago

35 comments

  • Havoc 4 hours ago

    > is available for all but the most up-to-date Kindles

    Bought one from eBay to try it out. Silly me connected it to wifi and suddenly it’s up to date and no longer breakable

    • jsheard 4 hours ago

      If you want a cheap rooted eReader I think you're better off getting a Kobo instead, they don't officially support rooting but AFAICT they make basically no effort to prevent it.

      • enthdegree an hour ago

        The latest Kobos use MediaTek SoCs with locked bootloaders. The Kobo Clara BW's MT8113, for example. As far as I know, one of the early bootloaders it, BL1, refuses to execute the next bootloader (BL2) unless its signature is valid. We can get the device into a mode where BL1 waits for upload of a BL2 via USB using an exploit called Kamakiri, but in public there is neither an exploit to get BL1 to boot an arbitrary BL2, nor an authorized BL2 image to upload. See here: https://github.com/bkerler/mtkclient/issues/1332

        Kobo devices have root exposed but don't let users boot their own kernels (and the kernel they ship was not compiled with kexec either).

        I really don't know the reason so many devices these days don't have an unlock method. It seems predatory. Who knows where in the chain this happens... maybe it's Kobo, or maybe MediaTek won't sell you their SoCs for mass-market devices unless you lock them.

        • monerozcash 29 minutes ago

          Can you just access /dev/mem or load a kernel module? Is there a SELinux policy stopping that?

          If you can do either of those, it should be trivial to get kexec working by just loading it as a module.

        • j45 2 minutes ago

          Older Kobos sound ok though?

      • tfsh 3 hours ago

        +1 to a Kobo, they cheaper and better than Kindles, with full Calibre support (https://github.com/kovidgoyal/calibre - OSS which has been in development for ~20 years!).

        The way you install additional software is literally just moving files into folders whilst its plugged into your computer. I'm sure it could handle Tailscale.

        • finalarbiter 2 hours ago

          I agree with your sentiment that the Kobo is better than the Kindle from an... ethical standpoint, if you have the money for one. However, it is worth noting that Kindles will always be cheaper than Kobo devices [0] due to economies of scale and lockscreen advertisements (removable with jailbreaking). From a pure cost perspective, and assuming the user is technically-minded enough to accomplish the jailbreak, the Kindle is likely always [1] a better deal.

          [0] as of today, 12/8/25, the "base model" Kindle 11th Generation is priced at $109.99 USD, and the respective Kobo Clara BW is $139.99 USD.

          [1] I say "likely always" to cover my bases. To my knowledge Calibre supports Kindle, just not as well as Kobo. That said I have found that the KOreader app is more than powerful enough for my use case (reading my own epubs, using dictionaries, etc.)

          • jsheard 2 hours ago

            That doesn't always hold, if you want color e-ink then Kobo is currently the cheaper option.

            Kindle Colorsoft (7" 16GB) - $250

            Kindle Colorsoft (7" 32GB) - $280

            Kobo Clara Color (6" 16GB) - $160

            Kobo Libra Color (7" 32GB) - $230

            The Libra also supports a stylus (sold separately) while the Colorsoft doesn't, that's reserved for the much bigger and pricier Kindle Scribe.

            • ekropotin 2 hours ago

              How is situation with latency on these readers?

              I’ve just acquired the latest gen Kindle and I’m absolutely blown away by how fast it is.

        • jrm4 2 hours ago

          Also consider koreader instead of the stock reader app.

          • cyberpunk 2 hours ago

            I kinda love that buried in the koreader menu somewhere is an option that drops me at a linux shell. I have no use really for this feature, but i like it. Good for those times you absolutely have to crank out some awk on the plane or whatever. :)

        • graemep 3 hours ago

          I use the Calibre support, but did not know you could install additional software that easily!

      • whoisburbansky 2 hours ago

        The only (tiny) issue I've had with Tailscale on Kobo has been that the tailscale daemon prevents me from using the Kobo in Mass Storage Mode while it's active, so I have to disable/quit KOReader to be able to plug it in again, which is admittedly not frequently warranted anyways.

      • kaladin-jasnah 3 hours ago

        Kobo is great. I use Plato and KOReader on mine. They worked better than the original reader software for reading manga.

  • d1egoaz 8 minutes ago

    I thought this was a random blog post, but it's coming directly from Tailscale, https://tailscale.com/blog/tailscale-jailbroken-kindle

  • vessenes 3 hours ago

    I used Tailscale on my remarkable tablet for a while; synchronizing documents over ssh is a lot easier with a static IP. It's fairly hard to get stuff to start on boot on the RM, or at least it was at the time, so I eventually moved off that plan. But it was pretty awesome to be able to ssh in from anywhere in the world.

    • svat 10 minutes ago

      Oh that sounds cool! What do you do now instead?

  • switz 2 hours ago

    I have tailscale running on my robot vacuum. It's my own little autonomous mesh vpn node that lets me connect back to my home network when I'm on the go.

  • _fzslm 3 hours ago

    You can also run Syncthing on a jailbroken Kindle. That opens up a world of possibilities!

    • epiccoleman 2 hours ago

      Whoa, now that sounds like the use case I've been looking for since I jailbroke mine.

      I have calibre set up to just email books to my Kindle, but that's an extra layer of indirection that I really don't need. I'll have to check that out.

      • boneitis an hour ago

        I too have heard about syncthing for the first time today but from a different submission[0] you might care to be aware of.

        Although, I realize Android != Kindle's OS, so I'm not sure how much concern there should be.

        [0]: https://news.ycombinator.com/item?id=46184730 "Syncthing-Android have had a change of owner/maintainer"

      • zikduruqe 2 hours ago

        If you have calibre, just turn on the wireless connection and have your Koreader connect to it.

        https://github.com/koreader/koreader/wiki/calibre

        • Cherub0774 an hour ago

          Personally I'm most fond of Calibre + Calibre-Web, which masquerades as the Kobo Store and lets you use the built-in Kobo syncing mechanisms with your Calibre library instead of having to do it all within Koreader.

  • fodkodrasz 2 hours ago

    This is pretty interesting write-up*, though I'm not sure my employer would be happy with me putting out EULA-violation instructions to our company homepage.

    * - at least for me, as the bugs in the stock reader drive me nuts, and have been waiting for this opportunity for a while

    • carlosjobim 2 hours ago

      I heard that a lord two provinces to the North had seven of his serfs severely whipped when he found out that they had been talking about how to violate the EULA. These agreements have to be respected!

  • citruscomputing 2 hours ago

    Oh, this will be very useful. My current solution is incredibly hacky, I run an unauthenticated SSH server on the Kindle (key-based wasn't working), port scan to find it, and SFTP new files. At home, at least, I have a static IP. The whole system falls apart enough that I usually just connect to calibre's remote server and send books that way, though. I wonder what the battery impact of running tailscale on a Kindle is.

  • jll29 an hour ago

    Kudos to all involved in freeing up Kindles around the world.

  • beepbooptheory an hour ago

    Love the splash Jameson quote in the first pic.

    > If everything means something else, than so does technology

  • marinhero 4 hours ago

    Excellent. This plus OPDS will make for easier transfer of files locally.

    • atrus 4 hours ago

      Or even not locally!

  • yegle 3 hours ago

    Now do Tesla! I had to resort to running an oauth-proxy to access my Plex on Tesla.

  • 2OEH8eoCRo0 3 hours ago

    What kernel version is it running?

    I wanted to add an old paperwhite to a kubernetes cluster and the ancient kernel held me back.