Quite frankly – this is the coolest named tool out there: John the Ripper.

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Often you’ll see it abbreviated as ‘JTR’ this is an awesome bit of hacking software that is designed to crack even very complicated passwords.

John the Ripper, mostly just referred to as simply, ‘John’ is a popular password cracking pentesting tool that is most commonly used to perform dictionary attacks. John the Ripper takes text string samples (from a text file, referred to as a ‘wordlist’, containing popular and complex words found in a dictionary or real passwords cracked before), encrypting it in the same way as the password being cracked (including both the encryption algorithm and key), and comparing the output to the encrypted string. This tool can also be used to perform a variety of alterations to dictionary attacks.

If you are somewhat confused between John the Ripper and THC Hydra then think of John the Ripper as an ‘offline’ password cracker whilst THC Hydra is an “online” cracker. Simple.

The conversation of which operating system is most secure, macOS vs. Windows, is an ongoing debate. Most will say macOS is more secure, but I'd like to weigh in by showing how to backdoor a MacBook in less than two minutes and maintain a persistent shell using tools already built into macOS.

Windows 10 is definitely not hackproof, but in this guide and upcoming articles, I'm hoping to help debunk the common misconception that macOS is more secure.

To my surprise, macOS does not use FileVault hard drive encryption (though it may ask to enable it during a clean macOS install/upgrade) by default. Those who do enable it may end up disabling it later due to slower write speeds or encrpytion negatively impacting the CPU. The absence of hard drive encryption allows attackers complete access to the files on a MacBook — without a password.

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Live Off the Land & Maintain Persistence

There are quite a few payloads, RATs, and backdoors which can be deployed against MacBooks. To keep things simple, I'll exercise a technique coined 'living off the land', which encourages penetration testers to utilize as many resources already present on the compromised device during post-exploitation attacks. This means not installing advanced payloads which actively evade antivirus detection but instead using applications which are already installed and will not be flagged as malicious.

Netcat (referred to as only nc from the command line) is a networking utility which can be used to create TCP or UDP connections. Its list of features includes port scanning, transferring files, and port listening to create backdoors into operating systems and networks. Netcat is one of the tools already built into macOS that will be utilized during this attack.

Cron is a task scheduler found in Unix-like operating systems such as Debian, Ubuntu, and macOS. Cronjobs are often used by system administrators to automate repetitive tasks, such as creating weekly backups, and executing a specific task when the OS reboots. To ensure the Netcat backdoor is always available, a cron job will be created to persistently open a new Netcat listener after it's closed.

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Step 1: Enable Single-User Mode

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To begin the attack, single-user mode (another feature of macOS), will be used. Single-user mode was designed for troubleshooting, debugging boot errors, and repairing disk issues, among many other administrative tasks. Unfortunately, single-user mode is very easily accessed and abused by hackers.

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To access single-user mode, power on the target MacBook while holding the Command + S buttons on the keyboard at the same time. Continue holding both of the keys until white text appears on the screen.