> 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.)
I use the Calibre support, but did not know you could install additional software that easily!
Kobo is great. I use Plato and KOReader on mine. They worked better than the original reader software for reading manga.
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.
Please share more details! This sounds so cool!
You can also run Syncthing on a jailbroken Kindle. That opens up a world of possibilities!
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.
Excellent. This plus OPDS will make for easier transfer of files locally.
Or even not locally!
Now do Tesla! I had to resort to running an oauth-proxy to access my Plex on Tesla.
What kernel version is it running?
I wanted to add an old paperwhite to a kubernetes cluster and the ancient kernel held me back.