Recently, my trusty Kindle Keyboard 3g died a warrior’s death, which is to say quietly and in its sleep with a particularly striking piece of Ellroy prose frozen on its screen. Amazon decided that the many books I’d bought from them did not matter more than the warranty being expired, and would only offer me versions of the Kindle I wasn’t interested in with marginal discounts as replacements. So I bought a used Kindle keyboard with just wireless from a friend, and that’s when I made my first mistake. First, the device itself was accessible as a hard drive even though the screen was frozen; that meant I could copy the (device locked) books along with ones I’d gotten from non-Amazon vendors and for free. However, I de-authorized it after doing so in order to free up space for the new device, which would become a problem later on, after I’d despaired of using Amazon’s built-in options to replace my books.

The main problem is that you can only send Kindle-purchased books one by one to your device, which combines neatly with the moronic decision not to allow you to easily manage folders and instead force you to manually juggle “collections” all over again, despite how Amazon claims it’s all backed up.  It is, but not in a useful way.

So if you have hundreds of books sorted into categories, you have a mess ahead of you. There are several options, for which the links below (in which helpful people like Athryn gave me a big hand) provide options.

1. Manually send all the Amazon books to your new kindle. Use Calibre plus the GUI collections plugin (C below) to reorganize everything before you die of old age.

2. Strip the DRM from your old backed up books (ie your documents folder on your Kindle) using option D. Copy that through USB to your new Kindle. Then use the Calibre plugin to sort them.
3. Give up on ebooks and return to the printed page.

I went with option 1 in the end because option 2 required me to learn how to get rid of both of the types of DRM that Amazon is using (kindle and Adobe Epub), which was a bridge too far relative to the task of going to the Kindle management page and clicking “send to device” 100+ times for just the books I definitely wanted. It’s embarrassing that Amazon couldn’t make this easier to back up and clone.

A. Kindle Diagnostic tool: crucial for obtaining your serial number if all that’s left of your kindle is a dead screen USB device (and you’ve de-registered it prematurely as I did).

B.How to back up your notes & clippings (especially first comment by Francisco about using the Kindle PC app)

C. Calibre GUI plugin that allows you to re-do your categories on your PC like Amazon should have done in the first place. Note that if you still have your old kindle and it works you can apparently export the categories using Kindle management on the Amazon website.

D. DRM removal software when all else fails with authorizations. I found the python standalone (DeDRM Applications Winapp) easier to use than the calibre option; the readme points you to the two links you need to get to get python scripts to work on your system. Once you enter your old Kindle’s Serial Number, you can just drag the kindle type documents to it and then…get error messages as the seemingly inevitable Adobe Epub DRM kicks in. So you can do this or just use the tools that come in that DRM software package.