https://arstechnica.com/information-technology/2019/11/what-the-newly-released-checkra1n-jailbreak-means-for-for-idevice-security/

It has been a week since the release of Checkra1n, the world’s first jailbreak for devices running Apple’s iOS 13. Because jailbreaks are so powerful and by definition disable a host of protections built into the OS, many people have rightly been eyeing Checkra1n—and the Checkm8 exploit it relies on—cautiously. What follows is a list of pros and cons for readers to ponder, with a particular emphasis on security.

First, Checkra1n is extremely reliable and robust, particularly for a tool that’s still in beta mode. It jailbreaks a variety of older iDevices quickly and reliably. It also installs an SSH server and other utilities, a bonus that makes the tool ideal for researchers and hobbyists who want to dig into the internals of their devices.