For whatever reason, it seems like a lot of the time the automatic updates that are supposed to happen just don’t. I’ve never had one of my Kindles prompt me to update; I’ve always had to do it manually.
Fortunately, manually updating your Kindle firmware isn’t all that hard. You just need to be able to connect your Kindle to your computer via USB, and then download the proper package(s).
If your older Kindle isn’t connecting to Amazon right now, you can probably already be sure you don’t have the latest firmware installed—but just in case you want to check for sure, go to the Kindle’s settings screen and tap the dropdown icon in the upper right, then choose “device info.” You should get a screen like this, that lists your device’s current firmware version. If it matches or exceeds the ones on this help screen, you’re good—but then, you probably already knew that you’re good because you’re still online with it.
If it’s lower, you need to make a note of the current version number, and go to whichever of these pages represents the model you have and download the firmware it tells you to. (List shamelessly borrowed from Nate Hoffelder’s post on this matter on The Digital Reader.)
Depending on what your current version is, it’s possible you might have to download more than one update package and then apply them one at a time.
If your Kindle isn’t on the above list, you probably don’t need to worry—and if you can’t connect to Amazon, you should contact Amazon support to find out why.
The update process is simple enough. When your Kindle is connected to your computer, your computer will see it as a USB disk drive. Simply copy the update you’re applying over to the Kindle’s root directory, just as you’d copy any file across.
After it’s copied, “eject” the Kindle using the USB icon in your Windows system tray (or, if you’re on a Mac, drag the Kindle to the trash). After it’s done, go back into the Kindle’s settings menu, tap the dropdown at the upper right, and choose “Update Your Kindle.” Your Kindle should then apply the update and reboot.
If you’re not able to get it to work, contact Amazon support to see if they can help. If they can’t get it to work, your model will likely be out of warranty by now like mine, but maybe they’ll offer you a discount on a new model, too.
For all that it’s occasionally necessary to update older Kindles manually to keep them working, at least they still do work with Amazon. Even the original first-generation Kindle can still connect and download e-books today just as it always has, assuming you have the proper update installed. Compare that to what’s happened recently to Nook owners in the UK, or owners of Sony readers a few years back. It’s good to see that Amazon seems to have the right idea regarding supporting its older hardware.