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.)
That doesn't always hold, if you want color e-ink then Kobo is currently the cheaper option.
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 only available on the much bigger and more expensive Kindle Scribe.
I kinda love that buried in the koreader menu somewhere is an option that drops me at a linux shell. I have no use really for this feature, but i like it. Good for those times you absolutely have to crank out some awk on the plane or whatever. :)
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.
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.
You can root certain models of robot vacuums and then ssh into them. Most run some variant of linux. Then just install tailscale. There are a few blogs out there of people who have done it[0][1].
It's taking a cloud-based product, de-clouding it, and then connecting it to your own private 'cloud'. Pretty cool all things told.
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.
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
I heard that a lord two provinces to the North had seven of his serfs severely whipped when he found out that they had been talking about how to violate the EULA. These agreements have to be respected!
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.
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.
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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