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Let's put Tailscale on a jailbroken Kindle

329 points| Quizzical4230 | 2 months ago |tailscale.com

86 comments

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Havoc|2 months 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|2 months 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.

devilbunny|2 months ago

Resell it, or wait six months. FWIW the 10th generation Kindle Paperwhite (the "PW4" in kindlemodding/mobileread lingo) doesn't have as large a screen as the newest models, but its maximum supported OS is currently 5.18.1 (and you can download that update directly from Amazon and transfer over USB), which is vulnerable to AdBreak. I just jailbroke and Tailscaled my PW4 this weekend after numerous failed attempts over a period of about a year to use the previous WinterBreak exploit.

I read mostly on my iPad; the Kindle is really just for reading outside, like at the beach/pool. But it was such a neat idea that I couldn't just pass it up.

cyberax|2 months ago

There is a new jailbreak, that is currently unpatched. You might need to make sure your Kindle doesn't get updated first by filling in all the disk space.

ycombinatrix|2 months ago

Been there before with the OG pixel.

IAmBroom|2 months ago

That's a (very) minor plotline in The Naked Gun (2025).

switz|2 months 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.

eyjafjallajokul|2 months ago

Please share more details! This sounds so cool!

wrxd|2 months ago

That’s cool, and unexpected from a corporate blog.

Ma favourite e-reader setup still is the Kobo + Booklore combination. Editing a configuration file on the device I can have it connect to my Booklore library that adds my own ebooks seamlessly on top of the one I can get from the Kobo store.

I haven’t setup Tailscale on it yet but it’s possible.

veverkap|2 months ago

Do you have any more information about this?

FlyingSnake|2 months ago

Kindles are amazing devices for hacking and turning into cute little dashboards. The kindle modding community is wonderful and full of people experimenting with it. If you have an old kindle, give it a new lease!

Shameless plug: I wrote about my experience here

https://samkhawase.com/blog/hacking-kindle/

Previous discussion: https://news.ycombinator.com/item?id=43822251

vessenes|2 months 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|2 months ago

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

sphars|2 months ago

If you're looking for a good resource on jailbreaking and installing KOReader on your Kindle, I highly recommend the guides at https://kindlemodding.org/

fodkodrasz|2 months 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 months 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!

_fzslm|2 months ago

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

epiccoleman|2 months 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.

pidgeon_lover|2 months ago

I've been experimenting with Syncthing on Kindle (https://github.com/Darthagnon/syncthing-kindle), but have had no luck seemingly because the Linux kernel included is too old and doesn't support network connections, or because the CPU is too weak.

Is there a project other than the one I forked?

jll29|2 months ago

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

citruscomputing|2 months 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.

marinhero|2 months ago

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

wkat4242|2 months ago

Yes and with kavita there's now even progress sync with koreader! I use it on my kindles too.

atrus|2 months ago

Or even not locally!

zaggynl|2 months ago

Can someone correct me on this: Is using Tailscale effectively putting your firewall at someone else's PC?

2OEH8eoCRo0|2 months 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.

humanfromearth9|2 months ago

Same for me. I wanted to use it for HPC...

beepbooptheory|2 months ago

Love the splash Jameson quote in the first pic.

> If everything means something else, than so does technology

yegle|2 months ago

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

skeptrune|2 months ago

yes, let's definitely do that