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While Chrome OS can run a linux virtual machine and you can install checkra1n, you cannot use it because you can't give it usb access to your device. In this tutorial, we're going to enable usb booting on your chromebook and then boot into checkn1x, a tiny linux distribution that you can run from a usb drive that has checkra1n and everything it needs to run pre-installed.
Before continuing, make sure you have a usb flash drive that you don't mind erasing as this process WILL WIPE ALL DATA ON THE DRIVE.
Back up your data
Enabling or disabling developer mode will wipe your chromebook. Most things like extensions, apps, docs, slideshows and such are saved to your google drive automatically and aren't saved locally. Anything stored locally however, such as things in the “My files” tab will be gone unless you upload them somewhere else, such as your google drive.
Enable developer mode
This process is the same on nearly all chromebooks but if it doesn't work for you, google “enable developer mode ” and you should find device specific instructions. First, power off your chromebook. Then, press and hold escape and the refresh button(F3) until you see a screen like this saying “Chrome OS is missing or damaged”. Don't worry, this is normal.


Go and setup your chromebook like normal before continuing to the next step.
Making a bootable usb
First, download the checkn1x iso from https://github.com/asineth0/checkn1x/releases. Next, download Chromebook Recovery Utility from the chrome web store and Checkn1x. Most Chromebooks are 64 bit so download the amd64 one. If that doesn't work, get the 32 bit one, i686. This utility is normally used to make Chromebook Recovery drives (hence the name), but we can trick it into flashing whatever OS we want. Change the extension of the file from .iso to .bin so Chromebook Recovery Utility can detect it. 

Enable usb booting
We now need to run this script to install the required extra software for usb booting. Press control, alt, and t together to open crosh(Chrome OS Shell). Then, type shell then press enter to get a full shell. Now run the following commands. cd; curl -LO mrchromebox.tech/firmware-util.sh sudo install -Dt /usr/local/bin -m 755 firmware-util.sh sudo firmware-util.sh You’ll now see the following gui. 
Boot Checkn1x
Make sure the usb is plugged in then reboot the Chromebook but rather than pressing control and D at the warning screen, press control and L. This will now open the bios. Press escape to select the boot device. It should just be the name of your usb. Wait a few moments and you should see the Checkra1n gui!
Jailbreak!
Just follow the on screen instructions to jailbreak your phone and reboot the Chromebook when finished. Just follow step 5 again when you need to re-jailbreak.
If you have any other issues, comment below or join the r/jailbreak discord server.
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