Here’s something I hadn’t thought about until recently: jailbreaking my Kindle. I came across advocates of this looking into the best way to download my Kindle book collection to my PC before they disabled some of the direct-download functionality I used.
Anyway, at the start of 2025, the “Winterbreak” exploit was released by “HackerDude” which lets you free any model of Kindle from the shackles of its Amazon overlords.
It does this in a way that doesn’t impact your Kindle’s standard features so you can still play just fine in the Kindle ecosystem. But, as ever with this stuff, I’m sure there are no guarantees and warranties are unlikely to be honoured if problems occur. Can’t say that I’ve heard of many permanent problems though.
Why would I want to do this? Well, apart from the whole ‘because I can’ and “to reduce Amazon’s surveillance of my habits and preferences” type stuff, my main functional motivation would be around the highlighting feature, which I use a lot.
Amazon offers that feature already, but with limitations. Right now, if you sideload a book - i.e. use a book you bought anywhere except the Amazon Kindle store, then any highlights and notes you make in it are largely stuck on the devices you use to read them on. Those highlights and notes don’t appear in your Amazon web notebook, which means that tools like Readwise can’t see them. There are workarounds, but they’re all a bit annoying.
Jailbreaking the Kindle would allow me to install non-Amazon reading software that doesn’t have that limitation - KO Reader seems to be what everyone in that world uses - which might be enough to make me do it.
Here’s a screenshot of KO Reader from its official website.
Amazon also has a weird feature where if you highlight “too much” of a book - the threshold can vary - then your highlights are truncated. Instead of full sentences you can end up with half a sentence followed by a “…”. I would guess this is some extremely lame anti-piracy thing? And I probably highlight too much, but still, I don’t like it. I bought the book. Let me highlight what I want. Using a non-Amazon reader software might be the way to never feel that pain again.
My only slight frustration will be the lack of a KO Reader iOS client for syncing reading positions. But when I think about it, I very rarely read the kind to book I want to take extensive notes or highlights from on any other devices anyway.