Here’s how to jailbreak iOS 14.4.1 and iPadOS 14.4.1 using the hugely popular checkra1n jailbreak utility the correct and easy way.

You can jailbreak both an iPhone and iPad so long as they are running iOS 14.4.1 and iPadOS 14.4.1. You will also need to use a Mac to complete the jailbreaking process as well.

Supported devices include:

  • iPhone 6s, 6s Plus, and SE
  • iPad 5th generation
  • iPad Air 2
  • iPad mini 4
  • iPad Pro 1st generation
  • Apple TV 4 and 4K
  • iBridge T2

The following devices aren’t currently supported but will be in a future update to checkra1n:

  • iPhone 7 and 7 Plus
  • iPad 6th and 7th generation
  • iPod touch 7
  • iPad Pro 2nd generation
  • iPhone 8, 8 Plus, and X

With all of that said and assuming you have all of the required hardware and software, here’s how you go about getting your jailbreak on.

Step 1: Head on over to checkra.in and download the latest version of the checkra1n jailbreak utility on your Mac.

Step 2: Find the DMG file that you just downloaded and install it into your /Applications folder on the Mac.

Step 3: If Apple’s security settings won’t allow your Mac to open the app, then follow the steps below. If everything opens as you would expect and no errors are shown on your display, then skip and move on to step 4:

  • Head into the System Preferences app and select the Security & Privacy option.
  • Select “Open Anyway” followed by “Open” and enter your administrator password when prompted.
  • Try to run the checkra1n app again and you shouldn’t have any issues.

Step 4: Launch the checkra1n app. Now open the checkra1n Options and check the “Allow untested iOS/iPadOS/tvOS versions” option. Select Back. This will allow you to jailbreak iOS 14.4.1 and iPadOS 14.4.1 if the version of checkra1n you are still using currently available does not officially support it yet.

Step 5: Connect your device via a Lightning cable and then click the Start button and select OK. Make sure that the checkra1n app continues to run.

Step 6: Choose “Next” and then follow the instructions that the checkra1n app dishes out to you. This will result in your device going into DFU Mode.

Step 7: The iPhone or iPad will reboot a few times during the process so don’t get concerned when that happens.

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