Let's put Tailscale on a jailbroken Kindle

Havoc wrote: post #2

> 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

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.

Re: Let's put Tailscale on a jailbroken Kindle

#5

Post by atrus » Mon, Dec 08, 2025, 5:18 PM UTC

marinhero wrote: post #3

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

Or even not locally!

Re: Let's put Tailscale on a jailbroken Kindle

#6

Post by tfsh » Mon, Dec 08, 2025, 5:33 PM UTC

jsheard wrote: post #4

Havoc wrote: post #2

> 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

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.

+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.

Re: Let's put Tailscale on a jailbroken Kindle

#7

Post by _fzslm » Mon, Dec 08, 2025, 5:41 PM UTC

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

Re: Let's put Tailscale on a jailbroken Kindle

#8

Post by 2OEH8eoCRo0 » Mon, Dec 08, 2025, 5:44 PM UTC

What kernel version is it running?

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

Re: Let's put Tailscale on a jailbroken Kindle

#9

Post by graemep » Mon, Dec 08, 2025, 5:47 PM UTC

tfsh wrote: post #6

jsheard wrote: post #4

Earlier quoted context omitted.

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.

+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.

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

Re: Let's put Tailscale on a jailbroken Kindle

#10

Post by vessenes » Mon, Dec 08, 2025, 5:48 PM UTC

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.