For iPhone 8, 8 Plus, and X on iOS 14, you must disable the passcode and "Skip A11 BPR check" in options for the jailbreak to work.
Checkra1n is a semi-tethered jailbreak based on the "checkm8" bootrom exploit. Because the exploit requires specific USB controller access, it traditionally only runs on macOS or Linux. "Justatech Checkra1n 0.4 Windows" (often provided as an ISO) is a community-modified version designed to bypass this limitation by booting a lightweight Linux environment on your PC. Download Justatech Checkra1n0 4Windows iso
💡 If you get a "USB Error" or "Error -20," try using a different USB port (preferably a USB 2.0 port) or a different Lightning cable. To help you get the best results, let me know: What model of iPhone/iPad are you using? What iOS version is currently installed? For iPhone 8, 8 Plus, and X on