Nook Classic Rooting Methods
From nookDevs
Nookdevs have found many methods of rooting the 1st generation eink Nook. Simultaneously, Barnes & Noble has released patches that render some of these techniques useless. After reading this page, you should have a better idea of which rooting method will be simplest to use. The most major factor is your nooks serial number: if it's less than 10030, the original softroot will work. Otherwise, you need to use a more complicated method.
No matter which method you use, the change is the same. All of them enable ADB, which allows you to install android packages using your computer. Once ADB is running, you should install the Wifi Locker. It keeps the nook awake so that you can work with it.
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For Old Nooks (Serial Number Below 10030)
Softroot
Softroot works with nooks whose serial number is less than 10030, provided that they're running software version 1.4.1. The softroot works by installing a fake update. You copy the nookdevs update to the nook, and it enables ADB. The nook can be downgraded to the version that it was running when you bought it, so you can use the softroot after downgrading to 1.4.1. If you're interested in the nuts and bolts, the developer wrote a great blog post.
Hard Root
Hard Root is an old method of rooting the nook. You must tear open the nook, pull out the MicroSD card, stick it in a computer running Linux, modify a file, then reassemble your nook. It's nearly impossible for Barnes & Noble to stop you from using this method, but there are much easier ways. It's strongly discouraged to use this method.
For New Nooks (Serial Number Above 10030)
The new nook doesn't accept unsigned sideloaded updates (the softroot). There are other methods for rooting, but none are as simple.
Router Based
To use this method, you need to change some administrative settings on your router so that sync.barnesandnoble.com resolves to a nookdevs server. When the nook asks for an update, it finds the nookdevs server and installs nookdevs update, which enables ADB.
No Router
If you can't change your routers settings, you can set your computer up as a hotspot. After installing software to create a wifi hotspot and a setting up a DNS server, you connect your nook to the computer over the new hotspot. It'll install the same update as in the router method.
Luck
Where all of the other methods are predictable, if tedious, this one requires luck. It exploits a bug in the browser: if the browser crashes and the nook's memory is in a certain state, ADB starts. Once it's running, you use your computer to gradually infiltrate the nook. The main advantage of this method is that it works with any 1st generation nook, regardless of software and hardware.