As a template I’ve been following Penetration Testing: A Hands-On introduction to Hacking by Georgia Weidman, so have been attempting to install the tools mentioned in the book. The major one being Kali Linux. Pairing this with the free Virtual Box on my MacBook Air is a great way of still being able to use macOS and all the tools I have on it without having to either buy another computer or reboot to a different operating system all the time.

However, a massive lesson from this has been that I’ll need to invest in my tools, as my nearly five year old MacBook Air with only 128GB storage is rapidly filling up. To solve this problem I purchased an external hard drive; but quickly found not only was it slow using this method, in the process of moving it back and forth between the external drive and internal; once Kali was back on my Mac it would no longer boot.

Setting up Kali the second time really helped me solidify installing things using terminal rather than a GUI (the most frustrating experience was installing Android studio which surprised me coming from a major company like Google).

In the book a Smartphone Penetration Testing Framework is also mentioned, but after much searching on the internet I’ve been unable to find it. There is a lesson in this problem though. The book was first published in 2014 and looking at the changes that have happened since then, being locked into following the book probably isn’t the best idea. While I’ll use the book as a guide for what to study and follow it for tips and ideas, I’ll look online as well as investigate personally into more up to date methods as I work through it.


A good friend recommended a package manager for macOS called Homebrew which I cannot explain how good I felt after using it. I’d tried to install a number of different tools solely using terminal and installing directly from source, but from one installation came many. I found that installing one tool would require a number of dependencies (and perhaps those tools required their own dependencies like electronic matryoshka dolls), but Homebrew makes it easy. As Homebrew installs the tool you want; you can see as it pulls any dependency that tool needs as well. Combined with Brew Formulas to find out what you can install with Homebrew saves a massive amount of time.