The error "p0sixspwn requires iTunes 10.5 or above" is a classic roadblock for legacy jailbreakers in 2021 and beyond. Despite the message, simply installing the latest version of iTunes won't fix it. The issue stems from the way modern iTunes versions handle mobile device drivers, which the older p0sixspwn tool cannot communicate with.

  1. Uninstall everything Apple from Control Panel. Remove iTunes, Bonjour, Apple Software Update, Apple Mobile Device Support, and iCloud. Reboot.
  2. Download iTunes 11.0.5 (32-bit or 64-bit depending on your OS; 64-bit preferred). Archive.org or oldversion.com are your friends here. The filename is usually iTunes64Setup.exe from 2013.
  3. Install iTunes 11.0.5. Do not let it auto-update. Disable Apple Software Update.
  4. Connect your iPhone 4S/iPad 2. If iOS asks to "Trust this computer," accept.
  5. Run p0sixspwn.exe as Administrator. The error will disappear, and the "Jailbreak" button will become clickable.

Alternative: Ditch p0sixspwn Entirely

By 2021+, the p0sixspwn tool is largely obsolete and unstable on modern PCs. The community has moved to better tools:

p0sixspwn was designed for 32-bit drivers. Modern versions of iTunes (especially the Microsoft Store version) use updated 64-bit drivers that make the device "invisible" to the jailbreak tool. Even if iTunes sees your phone, p0sixspwn will report that it doesn't meet the version requirements or simply won't detect the device. Step-by-Step Fix (2021 Update) 1. Completely Uninstall Existing Apple Software

Reboot your PC.

The Solution: How to Trick p0sixspwn in 2021

You have three proven methods to bypass this error. Do not try to modify the p0sixspwn.exe binary—you will break the digital signature, and the exploit will fail.

Use an original Apple 30-pin cable; many third-party cables lack the data lines required for jailbreaking.