Robert Shimonski - Penetration Testing For Dummies

You’re going to need a wide variety of skills throughout your pen testing career, but the biggest (or most important) skills to have are in the realm of networking and general security, which I discuss in this section.

Having an understanding of an organization’s business model and industry will enable you to take a holistic approach to security practices. Gaining that holistic view may require programming, network engineering, and system engineering, as well as understanding endpoints, desktops, storage, and many other systems and services. This doesn’t mean you can’t practice security if you don’t have all these other skills, but it definitely makes a difference on your ability to strategize and lead a security effort, and/or be able to respond to security threats, breaches, and attacks with better efficiency.

Security in a holistic view is also known as defense in depth . Confidentiality, integrity, and availability (CIA) make up a triad and defense in depth and pen testing helps to secure it, which is essentially the entire holistic view of practicing security in an organization.

To be able to conduct a pen test with any amount of confidence, the more you know about security and network architecture, the better. For example, to run a basic pen test, you need to enter a network address or subnet range in your scanning tool.

You need to also know the difference between vulnerability scanning and pen testing and why they’re similar and how they’re different. Figure 1-1 shows the basics of setting up an IP addressing range to scan and identify vulnerabilities. After you know the risks and weaknesses, you can then move into the details on how to exploit (pen test) what has been found so you can learn whether the technology is secured.

FIGURE 1-1:Adding an IP range to scan.

It’s also crucial to understand IP, protocols, networking, and other technologies related (and also not directly related) to security analysis because as weaknesses are identified (perhaps with a scan), then you can then move to exploit them (pen test) no matter what technology you’re presented with (database, mainframes, virtualized systems, for example).

In the following sections, I outline what knowledge you need to be a successful pen tester.

No stone is unturned as a pen tester, and what you need to expect is everything and anything. You are tested just as much as the systems you’re testing. Additionally, criminal activity isn’t confined to computers. The Internet of things (IOT) is an ever-expanding network of connected devices that includes, but is not limited to, tablets, phones, and smarthome devices such as TVs and thermostats. You may not encounter all those devices working as a professional pen tester in the corporate world, but you need to be aware of all connected devices. And when you’re pen testing, take time to find out which devices could be affected, such as mobile devices and assets used by field staff.

Also be aware of a hacker’s reconnaissance procedures. Hackers often begin attacks by using general research techniques, such as Internet searches that point a hacker in a direction, to learn more about accessing your company. For example, a simple Whois search might provide an address. A DNS search or query could provide a clue. Google searches may help to identify paths of attack, URLs, domain names, IPs, email addresses, and more. See Chapter 2for more about reconnaissance.

Basic networking includes, but is not limited to, understanding the OSI (open systems interconnect) model. Knowing how data transits from one location (a sender) to another (a receiver) is key to being able to unwind how many attacks occur.

It also includes knowing how routers, switches, hubs, load balancers, firewalls, intrusion prevention devices, and other network black boxes on the wire work. ( Black-box security testing refers to testing software security from the outside in. Generally, the tester has little or no knowledge of the internal workings.) If you pen test a router, you need to know how it operates.

The TCP/IP protocol suite also falls under basic networking knowledge. The transmission control protocol (TCP) and Internet protocol (IP) controls how computers connect to the Internet. It includes many of the protocols in the 7-layer OSI model. The Open Systems Interconnection (OSI) model is used as a logical framework to show how data travels from the source to the destination and back to the source through the many technologies that comprise the network, systems, and applications. It’s a model of standards that shows the under the hood actions of the technologies at each layer. Figure 1-2 shows an example of the OSI model.

FIGURE 1-2:Examining the OSI model.

The protocols used in a suite (such as TCP/IP) map to the various layers of the model and perform different functions. For example, FTP operates at a higher layer in the model than TCP or IP. The theory is that, if the lower layers don’t work, then the higher layer protocols won’t operate correctly. The OSI allows you to troubleshoot problems in a workflow manner.

Figure 1-3 shows a wire packet capture that shows a lot of the information you need to read through to conduct a pen test with a tool such as Wireshark. Here you can see packets that when captured can be decoded to tell you the details within them.

Having knowledge of these protocols, how and where they operate, and what is contained in the frames, headers, and other inner details of the packet is what will make you a great pen tester. If you run a pen test and it reports back, for example, that you have a vulnerability in telnet that’s sending packets back and forth in cleartext, you need to determine what path a hacker may take. You can more easily make that determination if you know how the protocols work and what is expected behavior and what can be manipulated versus what could be impacted by a software bug. This way, you can test it yourself first to identify whether you have an issue that might need to be remediated or mitigated.

I highly recommend that you study more on TCP/IP. It’s the main protocol suite in use today across the world; when it was first put into production many years ago it came with many flaws. Its ease of use is one of the biggest flaws and the fact that security was an afterthought behind usability. That said, today’s networks and systems can account for these flaws, but there is always danger in the shadows. Study TCP/IP and all of its sub-protocols and how they work to get better at testing weaknesses in your enterprise.

FIGURE 1-3:Digging into a network packet capture.