In this article by Jason Beltrame, authors of the book Penetration Testing Bootcamp, Proper planning and preparation is key to a successful penetration test. It is definitely not as exciting as some of the tasks we will do within the penetration test later, but it will lay the foundation of the penetration test. There are a lot of moving parts to a penetration test, and you need to make sure that you stay on the correct path and know just how far you can and should go. The last thing you want to do in a penetration test is cause a customer outage because you took down their application server with an exploit test (unless, of course, they want us to get to that depth) or scanned the wrong network. Performing any of these actions would cause our penetration-testing career to be a rather short-lived career.

In this article, following topics will be covered:

Why does penetration testing take place?
Building the systems for the penetration test
Penetration system software setup

(For more resources related to this topic, see here.)

Why does penetration testing take place?

There are many reasons why penetration tests happen. Sometimes, a company may want to have a stronger understanding of their security footprint. Sometimes, they may have a compliance requirement that they have to meet. Either way, understanding why penetration testing is happening will help you understand the goal of the company. Plus, it will also let you know whether you are performing an internal penetration test or an external penetration test. External penetration tests will follow the flow of an external user and see what they have access to and what they can do with that access. Internal penetration tests are designed to test internal systems, so typically, the penetration box will have full access to that environment, being able to test all software and systems for known vulnerabilities. Since tests have different objectives, we need to treat them differently; therefore, our tools and methodologies will be different.

Understanding the engagement

One of the first tasks you need to complete prior to starting a penetration test is to have a meeting with the stakeholders and discuss various data points concerning the upcoming penetration test. This meeting could be you as an external entity performing a penetration test for a client or you as an internal security employee doing the test for your own company. The important element here is that the meeting should happen either way, and the same type of information needs to be discussed.

During the scoping meeting, the goal is to discuss various items of the penetration test so that you have not only everything you need, but also full management buy-in with clearly defined objectives and deliverables. Full management buy-in is a key component for a successful penetration test. Without it, you may have trouble getting required information from certain teams, scope creep, or general pushback.

Building the systems for the penetration test

With a clear understanding of expectations, deliverables, and scope, it is now time to start working on getting our penetration systems ready to go. For the hardware, I will be utilizing a decently powered laptop. The laptop specifications are a Macbook Pro with 16 GB of RAM, 256 GB SSD, and a quad-core 2.3 Ghz Intel i7 running VMware Fusion. I will also be using the Raspberry Pi 3. The Raspberry Pi 3 is a 1.2 Ghz ARMv8 64-bit Quad Core, with 1GB of RAM and a 32 GB microSD. Obviously, there is quite a power discrepancy between the laptop and the Raspberry Pi. That is okay though, because I will be using both these devices differently. Any task that requires any sort of processing power will be done on the laptop. I love using the Raspberry Pi because of its small form factor and flexibility. It can be placed in just about any location we need, and if needed, it can be easily concealed.

For software, I will be using Kali Linux as my operating system of choice. Kali is a security-oriented Linux distribution that contains a bunch of security tools already installed. Its predecessor, Backtrack, was also a very popular security operating system. One of the benefits of Kali Linux is that it is also available for the Raspberry Pi, which is perfect in our circumstance. This way, we can have a consistent platform between devices we plan to use in our penetration-testing labs. Kali Linux can be downloaded from their site at https://www.kali.org. For the Raspberry Pi, the Kali images are managed by Offensive Security at https://www.offensive-security.com.

Even though I am using Kali Linux as my software platform of choice, feel free to use whichever software platform you feel most comfortable with. We will be using a bunch of open source tools for testing. A lot of these tools are available for other distributions and operating systems.

Penetration system software setup

Setting up Kali Linux on both systems is a bit different since they are different platforms. We won't be diving into a lot of details on the install, but we will be hitting all the major points. This is the process you can use to get the software up and running.

We will start with the installation on the Raspberry Pi:

Download the images from Offensive Security at https://www.offensive-security.com/kali-linux-arm-images/.
Open the Terminal app on OS X.
Using the utility xz, you can decompress the Kali image that was downloaded:
```
xz-dkali-2.1.2-rpi2.img.xz
```
Next, you insert the USB microSD card reader with the microSD card into the laptop and verify the disks that are installed so that you know the correct disk to put the Kali image on:
```
diskutillist
```
Once you know the correct disk, you can unmount the disk to prepare to write to it:
```
diskutilunmountDisk/dev/disk2
```
Now that you have the correct disk unmounted, you will want to write the image to it using the dd command. This process can take some time, so if you want to check on the progress, you can run the Ctrl + T command anytime:
```
sudoddif=kali-2.1.2-rpi2.imgof=/dev/disk2bs=1m
```
Since the image is now written to the microSD drive, you can eject it with the following command:
```
diskutileject/dev/disk2
```
You then remove the USB microSD card reader, place the microSD card in the Raspberry Pi, and boot it up for the first time. The default login credentials are as follows:
```
Username:root
Password:toor
```
You then change the default password on the Raspberry Pi to make sure no one can get into it with the following command:
```
Passwd<INSERTPASSWORDHERE>
```
Making sure the software is up to date is important for any system, especially a secure penetration-testing system. You can accomplish this with the following commands:
```
apt-getupdate
apt-getupgrade
apt-getdist-upgrade
```
After a reboot, you are ready to go on the Raspberry Pi.
Next, it's onto setting up the Kali Linux install on the Mac. Since you will be installing Kali as a VM within Fusion, the process will vary compared to another hypervisor or installing on a bare metal system. For me, I like having the flexibility of having OS X running so that I can run commands on there as well:

Similar to the Raspberry Pi setup, you need to download the image. You will do that directly via the Kali website. They offer virtual images for downloads as well. If you go to select these, you will be redirected to the Offensive Security site at https://www.offensive-security.com/kali-linux-vmware-virtualbox-image-download/.
Now that you have the Kali Linux image downloaded, you need to extract the VMDK. We used 7z via CLI to accomplish this task:
Since the VMDK is ready to import now, you will need to go into VMware Fusion and navigate to File | New. A screen similar to the following should be displayed:
Click on Create a custom virtual machine. You can select the OS as Other | Other and click on Continue:
Now, you will need to import the previously decompressed VMDK. Click on the Use an existing virtual disk radio button, and hit Choose virtual disk. Browse the VMDK. Click on Continue. Then, on the last screen, click on the Finish button. The disk should now start to copy. Give it a few minutes to complete:
Once completed, the Kali VM will now boot. Log in with the credentials we used in the Raspberry Pi image:
```
Username:root
Password:toor
```
You need to then change the default password that was set to make sure no one can get into it. Open up a terminal within the Kali Linux VM and use the following command:
```
Passwd<INSERTPASSWORDHERE>
```
Make sure the software is up to date, like you did for the Raspberry Pi. To accomplish this, you can use the following commands:
```
apt-getupdate
apt-getupgrade
apt-getdist-upgrade
```
Once this is complete, the laptop VM is ready to go.

Summary

Now that we have reached the end of this article, we should have everything that we need for the penetration test. Having had the scoping meeting with all the stakeholders, we were able to get answers to all the questions that we required.

Once we completed the planning portion, we moved onto the preparation phase. In this case, the preparation phase involved setting up Kali Linux on both the Raspberry Pi as well as setting it up as a VM on the laptop. We went through the steps of installing and updating the software on each platform as well as some basic administrative tasks.