A beginner's guide to setting up a pentest environment on macOS
Inspired by nicolahery's mac-dev-setup
- System update
- System preferences
- Security
- iTerm2
- Homebrew
- Git
- Visual Studio Code
- Python
- Node.js
- Apps
First thing you need to do, on any OS actually, is update the system! For that: Apple Icon > About This Mac then Software Update....
If this is a new computer, there are a couple of tweaks I like to make to the System Preferences. Feel free to follow these, or to ignore them, depending on your personal preferences.
In Apple Icon > System Preferences:
- Trackpad > Tap to click
- Keyboard > Key Repeat > Fast (all the way to the right)
- Keyboard > Delay Until Repeat > Short (all the way to the right)
- Dock > Automatically hide and show the Dock
I recommend checking that basic security settings are enabled.
In Apple Icon > System Preferences:
- Users & Groups: If you haven't already set a password for your user during the initial set up, you should do so now
- Security & Privacy > General: Require password immediately after sleep or screen saver begins
- Security & Privacy > FileVault: Make sure FileVault disk encryption is enabled
Since we're going to be spending a lot of time in the command-line, let's install a better terminal than the default one. Download and install iTerm2.
In Finder, drag and drop the iTerm Application file into the Applications folder.
You can now launch iTerm, through the Launchpad for instance.
Let's just quickly change some preferences. In iTerm2 > Preferences..., under the tab General, uncheck Confirm closing multiple sessions and Confirm "Quit iTerm2 (Cmd+Q)" command under the section Closing.
In the tab Profiles, create a new one with the "+" icon, and rename it. Then, select Other Actions... > Set as Default. Under the section Window, change the size to something better, like Columns: 125 and Rows: 35.
When done, hit the red "X" in the upper left (saving is automatic in macOS preference panes). Close the window and open a new one to see the size change.
Package managers make it so much easier to install and update applications (for Operating Systems) or libraries (for programming languages). The most popular one for macOS is Homebrew.
An important dependency before Homebrew can work is the Command Line Developer Tools for Xcode. These include compilers that will allow you to build things from source. You can install them directly from the terminal with:
xcode-select --install
Once that is done, we can install Homebrew by copy-pasting the installation command from the Homebrew homepage inside the terminal after we read the source carefully 😉:
/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install.sh)"
Follow the steps on the screen. You will be prompted for your user password so Homebrew can set up the appropriate permissions.
Once installation is complete, you can run the following command to make sure everything works:
brew doctor
To install a package (or Formula in Homebrew vocabulary) simply type:
brew install <formula>
To see if any of your packages need to be updated:
brew outdated
To update a package:
brew upgrade <formula>
Homebrew keeps older versions of packages installed, in case you want to rollback. That rarely is necessary, so you can do some cleanup to get rid of those old versions:
brew cleanup
To see what you have installed (with their version numbers):
brew list --versions
A nice extension to Homebrew is Homebrew Services. It will automatically launch things like databases when your computer starts, so you don't have to do it manually every time.
Homebrew Services will automatically install itself the first time you run it, so there is nothing special to do.
After installing a service (for example a database), it should automatically add itself to Homebrew Services. If not, you can add it manually with:
brew services <formula>
Start a service with:
brew services start <formula>
At anytime you can view which services are running with:
brew services list
macOS comes with a pre-installed version of Git, but we'll install our own through Homebrew to allow easy upgrades and not interfere with the system version. To do so, simply run:
brew install git
When done, to test that it installed fine you can run:
which git
The output should be /usr/local/bin/git.
On a Mac, it is important to remember to add .DS_Store (a hidden macOS system file that's put in folders) to your project .gitignore files. You also set up a global .gitignore file, located for instance in your home directory (but you'll want to make sure any collaborators also do it):
cd ~
curl -O https://raw.githubusercontent.com/avarx/mac-sec-setup/master/.gitignore
git config --global core.excludesfile ~/.gitignore
Go ahead and download it. Open the .dmg file, drag-and-drop in the Applications folder, you know the drill now. Launch the application.
Note: At this point I'm going to create a shortcut on the macOS Dock for both for Visual Studio Code and iTerm. To do so, right-click on the running application and select Options > Keep in Dock.
Just like the terminal, let's configure our editor a little. Go to Code > Preferences > Settings. In the very top-right of the interface you should see an icon with brackets that appeared { } (on hover, it should say "Open Settings (JSON)"). Click on it, and paste the following:
{
"editor.tabSize": 2,
"editor.rulers": [80],
"files.insertFinalNewline": true,
"files.trimTrailingWhitespace": true,
"workbench.editor.enablePreview": false
}Feel free to tweak these to your preference. When done, save the file and close it.
Pasting the above JSON snippet was handy to quickly customize things, but for further setting changes feel free to search in the "Settings" panel that opened first (shortcut Cmd+,). When you're happy with your setup, you can save the JSON to quickly restore it on a new machine.
If you remember only one keyboard shortcut in VS Code, it should be Cmd+Shift+P. This opens the Command Palette, from which you can run pretty much anything.
Let's open the command palette now, and search for Shell Command: Install 'code' command in PATH. Hit enter when it shows up. This will install the command-line tool code to quickly open VS Code from the terminal. When in a projects directory, you'll be able to run:
cd myproject/
code .
VS Code is very extensible. To customize it further, open the Extensions tab on the left.
Let's do that now to customize the color of our editor. Search for the Atom One Dark Theme extension, select it and click Install. Repeat this for the Atom One Light Theme.
Finally, activate the theme by going to Code > Preferences > Color Theme and selecting Atom One Dark (or Atom One Light if that is your preference).
macOS, like Linux, ships with Python already installed. But you don't want to mess with the system Python (some system tools rely on it, etc.), so we'll install our own version using pyenv. This will also allow us to manage multiple versions of Python (ex: 2.7 and 3) should we need to.
Install pyenv via Homebrew by running:
brew install pyenv
When finished, you should see instructions to add something to your profile. Open your .bash_profile in the home directory (you can use code ~/.bash_profile), and add the following line:
if command -v pyenv 1>/dev/null 2>&1; then eval "$(pyenv init -)"; fiSave the file and reload it with:
source ~/.bash_profile
Before installing a new Python version, the pyenv wiki recommends having a few dependencies available:
brew install openssl readline sqlite3 xz zlib
We can now list all available Python versions by running:
pyenv install --list
Look for the latest 3.x version (or 2.7.x), and install it (replace the .x.x with actual numbers):
pyenv install 3.x.x
List the Python versions you have locally with:
pyenv versions
The star (*) should indicate we are still using the system version, which is the default. I recommend leaving it as the default as some Node.js packages will use it in their installation process.
You can switch your current terminal to another Python version with:
pyenv shell 3.x.x
You should now see that version when running:
python --version
In a project directory, you can use:
pyenv local 3.x.x
This will save that project's Python version to a .python-version file. Next time you enter the project's directory from a terminal, pyenv will automatically load that version for you.
For more information, see the pyenv commands documentation.
pip was also installed by pyenv. It is the package manager for Python.
Here are a couple Pip commands to get you started. To install a Python package:
pip install <package>
To upgrade a package:
pip install --upgrade <package>
To see what's installed:
pip freeze
To uninstall a package:
pip uninstall <package>
virtualenv is a tool that creates an isolated Python environment for each of your projects.
For a particular project, instead of installing required packages globally, it is best to install them in an isolated folder, that will be managed by virtualenv. The advantage is that different projects might require different versions of packages, and it would be hard to manage that if you install packages globally.
Instead of installing and using virtualenv directly, we'll use the dedicated pyenv plugin pyenv-virtualenv which will make things a bit easier for us. Install it via Homebrew:
brew install pyenv-virtualenv
After installation, add the following line to your .bash_profile:
if which pyenv-virtualenv-init > /dev/null; then eval "$(pyenv virtualenv-init -)"; fiAnd reload it with:
source ~/.bash_profile
Now, let's say you have a project called myproject. You can set up a virtualenv for that project and the Python version it uses (replace 3.x.x with the version you want):
pyenv virtualenv 3.x.x myproject
See the list of virtualenvs you created with:
pyenv virtualenvs
To use your project's virtualenv, you need to activate it first (in every terminal where you are working on your project):
pyenv activate myproject
If you run pyenv virtualenvs again, you should see a star (*) next to the active virtualenv.
Now when you install something:
pip install <package>
It will get installed in that virtualenv's folder, and not conflict with other projects.
You can also set your project's .python-version to point to a virtualenv you created:
pyenv local myproject
Next time you enter that project's directory, pyenv will automatically load the virtualenv for you.
The recommended way to install Node.js is to use nvm (Node Version Manager) which allows you to manage multiple versions of Node.js on the same machine.
Install nvm by copy-pasting the install script command into your terminal.
Once that is done, open a new terminal and verify that it was installed correctly by running:
command -v nvm
View the all available stable versions of Node with:
nvm ls-remote --lts
Install the latest stable version with:
nvm install node
It will also set the first version installed as your default version. You can install another specific version, for example Node 10, with:
nvm install 10
And switch between versions by using:
nvm use 10
nvm use default
See which versions you have install with:
nvm ls
Change the default version with:
nvm alias default 10
In a project's directory you can create a .nvmrc file containing the Node.js version the project uses, for example:
echo "10" > .nvmrc
Next time you enter the project's directory from a terminal, you can load the correct version of Node.js by running:
nvm use
Installing Node also installs the npm package manager.
To install a package:
npm install <package> # Install locally
npm install -g <package> # Install globally
To install a package and save it in your project's package.json file:
npm install --save <package>
To see what's installed:
npm list --depth 1 # Local packages
npm list -g --depth 1 # Global packages
To find outdated packages (locally or globally):
npm outdated [-g]
To upgrade all or a particular package:
npm update [<package>]
To uninstall a package:
npm uninstall --save <package>
Download Docker for Mac and double-click Docker.dmg to start the install process. When the installation completes and Docker starts, the whale in the top status bar shows that Docker is running, and accessible from a terminal.
Run docker version to check that you have the latest release installed.
Run docker run hello-world to verify that Docker is pulling images and running as expected.
Simple:
docker pull kalilinux/kali-rolling
docker run -t -i kalilinux/kali-rolling /bin/bash
Dedicated:
docker run -d \
--rm \
-h ${ctf_name} \
--name ${ctf_name} \
-v $(pwd)/${ctf_name}:/ctf/work \
-p 23943:23943 \
kalilinux/kali-rolling
docker exec -it ${ctf_name} /bin/bash
Here is a quick list of some apps I use, and that you might find useful as well: