Jailbreak of any firmware after version 5.16.2.1.1 (June 2023) requires the Kindle to be connected and registered.
Anything prior to, and including this version, can be jailbroken with no registration.
The hardest part was finding the `Update` menu item. It's only visible if you go to Settings, then press the menu button again while on the Settings page.
Not sure if registering the Kindle was required.
Your post is making me want to try more Cloudflare Developer Platform stuff like Cloudflare Workers.