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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
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.
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.
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.
[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.)
You can also run Syncthing on a jailbroken Kindle. That opens up a world of possibilities!
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.
> 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.
* - at least for me, as the bugs in the stock reader drive me nuts, and have been waiting for this opportunity for a while
Earlier quoted context omitted.
+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 Kin…
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.