They block you from doing this if you're not logged in (as I discovered after wiping and rooting one to give to a friend recently).

As evidence, note that instructions for rooting them requires the device to be registered - this is because it won't be accessible over USB until you do so: https://kindlemodding.org/jailbreaking/WinterBreak/

So if you can't log in...

Not a thing on my e-ink kindle, although it is a decade old by now.

its not usb, it looks like micro usb but its custom. mine failed and i found out the hard way,

> The big problem is that Amazon no longer allows you to download books from their site to your desktop

I've bought a number of books on Kindle that were explicitly marked as being sold without DRM. Does this mean I've lost access to any DRM-free downloads that I haven't already backed up?

If you bought them from Amazon, you won't be able to get them after the cutoff date directly to that Kindle via WiFi. You may not be able to get them in a format that old Kindles can read at all.

Download and back them up now. Or just pirate them if you need them later.

The entire Kindle store system will cease working on older Kindles after the cutoff. Still works as a reader, but expect to lose things like location sync across devices.

I don't buy from Amazon, I don't turn on WiFi on my Kindle because it eats battery life, I always travel with a laptop, and I only use it to read outdoors. So I really don't care. It's my beach book. At home, I'd rather read on my iPad.

Oh, and FWIW, you can install Tailscale to a jailbroken Kindle and Taildrop files to it over WiFi, if it can read the format (for the old ones being discussed, that's mobi or azw3).