The checkra1n team (led by axi0mX and others) built the tool primarily on Unix-based systems (macOS and Linux). Porting the checkm8 exploit—which operates at a low-level USB layer—to Windows requires writing complex drivers and bypassing Windows' strict security architecture regarding USB peripherals. The developers have historically cited the difficulty of handling USB interaction on Windows as the primary reason for the delay.

Advanced users often run Linux (Ubuntu or Kali) via VirtualBox or VMware on Windows. However, this is tricky because the VM must correctly capture the USB device (the iPhone) during the DFU mode handshake. While possible, it is often unstable compared to a native boot.

Since checkra1n cannot run directly on Windows, the community uses lightweight Linux distributions that boot directly into the checkra1n interface.