FilterHN

Let's put Tailscale on a jailbroken Kindle

82 points

by Quizzical4230

2 hours ago

| past

| 9 comments

| tailscale.com

| HN

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fodkodrasz

5 minutes ago

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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

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citruscomputing

9 minutes ago

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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.

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Havoc

1 hour ago

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> 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

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jsheard

1 hour ago

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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.

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tfsh

1 hour ago

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+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.

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finalarbiter

14 minutes ago

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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.)

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jsheard

3 minutes ago

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That doesn't always hold, the color Kindles are currently more expensive than the color Kobos.

Kindle Colorsoft (7" 16GB) - $250

Kindle Colorsoft (7" 32GB) - $280

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

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

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graemep

59 minutes ago

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

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whoisburbansky

9 minutes ago

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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.

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kaladin-jasnah

35 minutes ago

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

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switz

21 minutes ago

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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.

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eyjafjallajokul

16 minutes ago

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Please share more details! This sounds so cool!

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_fzslm

1 hour ago

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

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epiccoleman

11 minutes ago

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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.

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vessenes

57 minutes ago

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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.

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marinhero

1 hour ago

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

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atrus

1 hour ago

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Or even not locally!

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yegle