Is it time to jailbreak my Kindle?

I love my Kindle, and I’m not particularly mad at Amazon, but I do think it might be time to jailbreak the thing so that I can a) explore different ways to use it, b) have a little technical-ish project to do while I’m on sabbatical, and c) educate myself on one more area of “big tech” and “big business” that might not be so great to rely on.

If you aren’t familiar with the concept of jailbreaking, here is a definition:

Jailbreaking means bypassing Amazon’s built-in restrictions to gain more control over the device. Normally, Kindles are locked into Amazon’s ecosystem, limiting file formats, forcing updates, and even allowing Amazon to delete books from your library. Jailbreaking removes these constraints.

I came across this video (HT Donwill) about why you might want to do this with a Kindle, with links to the Kindle Modding Wiki (and Discord group) with instructions on how to do it. Seems easy enough!

Why go through the hassle you say?

Maybe the most important reason is that I’d like to have the option to buy e-books from retailers other than Amazon for my device. Also, this process doesn’t remove the option to use the standard Kindle/Amazon services…it just adds a bunch more options.

The video above does a good job of going through some of the ways that it might be smart to have other ways besides the one retailer to rule them all to buy/manage e-books. I have 250+ books that I’ve bought via Kindle, and I don’t want to lose them, but I’ve also been using the local library more and more (Wake County Library system for me) and have been trying to get e-books through that route as well via Libby, which is what my library uses. Libby can send to Kindle devices, and I’m not planning to sever all ties with Amazon. It’s just, with all the reading I’m doing, it feels like a good time to broaden my options.

I’m curious if going through this process might be a gateway drug to breaking my reliance on Spotify for music as well. The prospect of exploring software like Calibre (e-book library management) and getting more into the technical how-to for jailbreaking sounds exciting and is scratching my nascent know how things work/right to repair DIY sensibilities.

I’ll report back on how it goes.

🗒 06.06 Update: I guess I missed the boat, at least for now. My Kindle is on firmware version 5.18.2 and as of this update the jailbreak method isn’t supported per the guide: Winterbreak/Mesquito does NOT work on firmware 5.18.1 and beyond.