Let's put Tailscale on a jailbroken Kindle

> 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.

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.)

Where do I get DRM-free ebooks to put on a Kobo? I don't support breaking DRM. So I'm using a Kindle because it has the best access to and integration with almost any book I want.

What does it mean to not support breaking DRM? You purchase something and then are fine not being able to use it?