How to Jailbreak iOS 14 on Mac with checkra1n

Q: Is there a checkra1n version for Windows?

No, there is no official checkra1n for Windows. checkra1n only ships builds for macOS and Linux. To jailbreak on a Windows PC, you'd need to run Linux in a virtual machine or set up a dual-boot Linux install, which is far more involved than jailbreaking directly on a Mac.

Q: Can I jailbreak iOS 14 without a computer?

No. Despite what some sites claim, there is no working no-computer or browser-based checkra1n online jailbreak. checkra1n has to run as a desktop application on a Mac or Linux machine that's physically connected to your iPhone via USB, and any site claiming otherwise is trying to scam you or install malware.

Q: In checkra1n, what is -39 error?

Error -39 almost always points to a USB connection or cable issue rather than a problem with checkra1n itself. Try a different USB cable, ideally the original Apple cable, plug directly into your Mac instead of through a hub, restart both the iPhone and the checkra1n app, and make sure you're running the latest checkra1n build before retrying the DFU steps.

How to Jailbreak iOS 14.x on Mac with checkra1n

Wondering how to jailbreak iOS 14 on a Mac? This guide walks through jailbreaking iOS 14.x with checkra1n, the free jailbreak tool built around the checkm8 bootrom exploit. Because checkm8 targets a hardware-level flaw in Apple’s A7–A11 chips, it can’t be patched by a software update — which is why checkra1n jailbreak on Mac is still the go-to method for these older iPhones, even years after iOS 14 first shipped. Whether you searched jailbreak iPhone Mac, checkrain iOS 14 (the correct spelling uses a numeral 1, not the letters “rain” — the real tool is checkra1n), or want to know how to jailbreak iPhone with MacBook specifically, the steps below cover the full process from download to Cydia.

This guide applies to iPhone X, 8 Plus, 8, 7 Plus, 7, SE (1st generation), 6S Plus, 6S, 6 Plus, 6, and 5S — the checkra1n compatible devices, all built on Apple’s A7 through A11 chips.

Is Jailbreaking iOS 14 Still Worth It?

These devices are now legacy hardware, but checkra1n remains the most reliable jailbreak for iOS 14 on this chip range because it exploits the bootrom rather than a patchable software bug. Common typo searches — checkra1 download, checkra1n, checkrain — all lead back to the same official tool. There’s no legitimate jailbreak iOS 14 no computer method, and sites promising a checkra1n online jailbreak that runs entirely in your browser are scams — checkra1n only runs as a desktop app on macOS or Linux. If you were hoping for a jailbreak iOS 14 Windows tool, none exists officially; on a Windows PC you’d need a Linux virtual machine or dual boot to run checkra1n, which is well outside the scope of a beginner tutorial. Always grab the checkra1n Mac OS build from the real checkra1n website, checkra.in — never a copycat mirror.

You Will Need

A Mac computer with an internet connection
A cable to connect your iPhone to your Mac
The iPhone you wish to jailbreak on hand, plus its lock screen passcode if it has one
The checkra1n tool — for a checkra1n iOS 14 download, only use the checkra1n official website, checkra.in. Avoid any other jailbreak iOS 14 download mirror; checkra1n is completely free, and anything asking for payment is a scam.

Step One
Go to the checkra1n official website at checkra.in and download the latest macOS build listed there — this is the only ios 14 jailbreak download link you should trust.

Step Two
Double-click the downloaded DMG file to open it, then drag the checkra1n icon onto the Applications folder icon.

Step Three
Open your Applications folder, then right-click (or Control-click) the checkra1n app and choose Open from the menu. macOS Gatekeeper flags unsigned apps like this by default, so this step is required the first time you launch it.

Click Open to confirm you’d like to launch the checkra1n app.

Step Four
Connect your iPhone to your Mac with a USB cable and click Start.

If you see a warning that your iOS version is untested, go to Options and select Allow untested iOS versions.

Step Five
Click Next to put your device into Recovery Mode, then follow checkra1n’s interactive jailbreak wizard to enter DFU mode. The procedure is:

Entering DFU Mode

1. Hold the Side button until your screen goes black, then release.
2. Hold the Side button and Volume Down button together for 5 seconds.
3. Release the Side button and keep holding Volume Down until your Mac shows that the device is in recovery mode. Your iPhone’s screen will stay black — that’s expected. Click Start to begin.

checkra1n detects recovery mode — Your Mac lets you know the device is in recovery mode.

Step Six
checkra1n now runs the jailbreak automatically. Leave your iPhone connected and don’t interrupt the process.

Step Seven
Launch the new checkra1n app icon on your iPhone’s home screen, tap Cydia, then tap the large Install Cydia button that appears. This checkra1n Cydia installation step is what people mean by “Cydia for Mac” — Cydia itself has no Mac app; the package manager installs on the iPhone, using your Mac only as the jailbreak host.

Step Eight
Cydia is now installed on your iPhone, and you can launch it from the home screen any time.

If you hit an error partway through, it’s usually because checkra1n hasn’t added official support for your exact iOS build yet, or your device sits outside the A7–A11 range it supports. This iPhone jailbreak iOS 14 method — like any jailbreak 14 project on this chip range — is completely free, and jailbreaking Mac requirements are minimal: macOS Big Sur (10.16) or later and a compatible iPhone. If anything asks you to pay for a jailbreak or for “premium” checkra1n access, don’t pay and don’t download it. Those are scams.

What’s Next: Installing SPYERA

Once the jailbreak is complete, you’ll see both the Cydia and checkra1n icons on your iPhone. Your device is now ready for SPYERA — installation instructions are available inside your SPYERA web account after signup. SPYERA can hide its own icon along with the Cydia and checkra1n icons, so the phone looks untouched once setup is done. On a jailbroken device like this, SPYERA can pull data that non-jailbroken monitoring can’t reach, including deep WhatsApp monitoring, an iPhone keylogger, and access to the remote camera. Only jailbreak and install monitoring software on a device you own or are legally authorized to manage, such as your minor child’s phone or a company-owned iPhone.

How do I jailbreak iOS 14 on a Mac?

Download checkra1n from the official checkra.in website, install it in your Applications folder, connect your compatible iPhone with a USB cable, then follow checkra1n’s interactive wizard to put the device into DFU mode. checkra1n handles the rest automatically and installs Cydia once the jailbreak finishes.

What are the checkra1n compatible devices?

checkra1n works on any device with an Apple A7 through A11 chip: iPhone 5S, 6, 6 Plus, 6S, 6S Plus, SE (1st generation), 7, 7 Plus, 8, 8 Plus, and X, along with several iPad and iPod touch models from the same generations. Newer iPhones (XS and later) use the A12 chip or newer and are not affected by the checkm8 exploit checkra1n relies on.

Is there a checkra1n version for Windows?

No — there is no official checkra1n for Windows. checkra1n only ships builds for macOS and Linux. To jailbreak on a Windows PC, you’d need to run Linux in a virtual machine or set up a dual-boot Linux install, which is far more involved than jailbreaking directly on a Mac.

Can I jailbreak iOS 14 without a computer?

No. Despite what some sites claim, there is no working “no computer” or browser-based checkra1n online jailbreak. checkra1n has to run as a desktop application on a Mac or Linux machine that’s physically connected to your iPhone via USB — any site claiming otherwise is trying to scam you or install malware.

In checkra1n, what is -39 error?

If you’re asking in checkra1n what is -39 error, it almost always points to a USB connection or cable issue rather than a problem with checkra1n itself. Try a different USB cable (ideally the original Apple cable), plug directly into your Mac instead of through a hub, restart both the iPhone and the checkra1n app, and make sure you’re running the latest checkra1n build before retrying the DFU steps.

Is checkra1n better than Pangu iOS 14 tools?

Pangu iOS 14 jailbreak tools are no longer maintained or safe to use, and most download links still circulating online are outdated or bundled with unwanted software. checkra1n is the actively supported option for A7–A11 devices and remains the recommended tool for jailbreaking iOS 14.x today.