Penetration Testing 101: What You Need to Know About Pen Testing

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Iran's uranium enrichment facilities were some of the most high-security buildings in the world. Not just with physical checkpoints and guards, but with air-gapped digital defenses. All of that security became moot in 2010 when Stuxnet devastated the facility. Read More

Iran’s uranium enrichment facilities were some of the most high-security buildings in the world. Not just with physical checkpoints and guards, but with air-gapped digital defenses. All of that security became moot in 2010 when Stuxnet devastated the facility.

Stuxnet was a tiny worm that took advantage of a zero-day vulnerability to do its wicked work. Needless to say, the Iranian IT security officers failed to do one thing: get pen testing. If they had known their own facility’s weaknesses, it might just have survived.

What is pen testing? In this guide, we’ll discuss how this cybersecurity exercise can strengthen your organization. With it, you’ll protect yourself better against an ocean’s-worth of daily cyber attacks.

What Is Pen Testing?

Pen testing is short for penetration testing. This is a planned exercise where a skilled white hat hacker team attempts to compromise a client’s system. The client pays this hacker team to do so in order to find vulnerabilities.

White hat hackers are the “good” kind of hackers. Rather than steal, blackmail, or sabotage, they use their skills for the benefit of humanity. They work under security firms that contract their services to companies large and small.

Hackers perform this infiltration just as black hat hackers–the bad kind–would. They use every trick up their sleeves and don’t pull any punches.

Think of it like a castle hiring an army to attempt a siege upon its defenses. That army uses everything at its disposal to break through the walls. In the process, they discover vulnerabilities that the castle can then patch up later.

Are Vulnerabilities Really That Bad?

At first glance, pen testing may seem quite extreme. Is it really necessary to perform a simulated cyber attack just to brush up on security? The answer is yes.

It’s important to understand how computer vulnerabilities work. In the cyber security industry there’s a saying: if they can hack it, they will. In other words, it’s only a matter of time before a hacker exploits your system’s vulnerabilities.

Every system has vulnerabilities. Further, it is impossible to get rid of them entirely. As long as there is a door to open, there is a means to open the door–legitimately or not.

This is why your software and operating systems constantly pester you with update notifications. In the majority of cases, these updates are not just feature upgrades. They include vital security patches to close off certain vulnerabilities.

How Hackers Exploit Vulnerabilities

Hackers never rest. And thanks to automation and AI, they can continue their work even when they sleep. Day and night, they are prying software and operating systems for vulnerabilities.

Once they find a vulnerability, they comb the Internet for devices with that vulnerability. Such as your systems.

Unfortunately, security breaches sometimes take months before anyone discovers that they happened. By the time they make that discovery, the damage has already been done. Companies then have to deal with the often staggering cost of recovery.

Even companies that are rigorous about their security are not invulnerable. They might update their software regularly, use encryption, and limit permissions. Yet still, hackers are able to slip through the cracks.

That’s where pen testing comes to the rescue.

How Pen Testing Works

The way one company performs pen testing will be different from the next. Some even provide automated pen testing. In that spirit, we will be providing a general outline of how it works.

Reconnaissance and Planning

Before pen testing begins, the team in charge seeks to establish the intended goal. Are they looking to compromise the entire system root to stem, or are they stress-testing only a portion of it? They also establish the extent to which they will perform the test.

Every company is different, from its systems to the way it uses them. A pen testing team will then gather intelligence. They will collect all sorts of information, from network details to the system’s setup.

Once they have the information they need, the next stage begins.


Now, the hackers passively–or actively–observe how the system performs from a distance. Real-life hackers will often spend days, weeks, or months just listening. The intention is to understand how the system works and get a rough idea of potential vulnerabilities.

Gain Access

Now the “fun” begins. The team of white hat hackers uses all the tools they have. They might escalate privileges, intercept traffic, inject SQL commands, and much more.

This starts as a sort of “throw everything at the wall and see what sticks” situation. Hackers try to exploit after exploit until something works. In the process, they attempt to steal data and deepen their control of the system.

Maintain Access

Gaining access is one thing, but it’s worth nothing without the ability to keep it. Sometimes, your defensive measures are enough to thwart certain attacks after they have happened. During this stage, though, hackers hang on to what access they have and try to expand it.

Again, it can take months before an organization discovers a security breach. Hackers will maintain their access during this entire period and siphon out as much data as they can. If they plan to implement ransomware, they begin encrypting your files.

Final Analysis

At this point, pen testing has come to a close. The team of pen testers reconvenes with everything they have learned in the process. They compile a detailed report on their findings with information such as the following:

  • Vulnerabilities they discovered and exploited
  • Any confidential or sensitive data they accessed in the process
  • How long they were able to retain their counterfeit privileges before the detection

Other Testing Methods

Of course, there are other approaches and methodologies for pen testing. For example, in blind testing: pen testers only get the name of the company and nothing else. They have to perform the evaluation from scratch with no further intel.

There are internal testing exercises that might simulate an inside job. If a disgruntled employee were to try to take down the system from within, this could demonstrate how they might do it.

There is also targeted testing. Think of this as a competition between the testers and security personnel. The security team is being “graded” on their performance by the hackers.

What Does the Target Company Do during Pen Testing?

The important thing with pen testing is that the company undergoing the test acts “normally.” After all, you never know when hackers have targeted your company. You never know what they’re doing until someone discovers the breach.

This all happens at random, without your knowledge, until you uncover a breach. This is the other half of blind testing–i.e., the tested organization has no knowledge. In most test situations, this is the best testing method.

A pen testing team is not just testing your systems. They are testing the people behind them that are handling security.

Sure, it’s important that your IT team be on their “best behavior.” But a successful pen-testing job works best when only a select few know the particulars. An organic, ignorant reaction to the pen testing team’s endeavors produces real-world results.

Remember, this is not a test in the traditional sense of passing or failing. If there is a possibility of failure, you want to fail so that you can see why you failed. The whole purpose is to discover the vulnerabilities that leave holes for hackers to squeeze through.

Benefits of Penetration Testing

Major organizations, from multinational corporations to government entities, hire pen-testing teams. Regardless, what is the benefit to you of contracting a pen testing evaluation?

Improved Security

Remember our analogy about the castle? Penetration testing allows somebody who has no familiarity with your system to see it with new eyes. They will identify problems that you would normally be blind to.

Think of it as a mock security breach with no consequences. A war game that prevents any war.

Better Understanding of Your Systems

A simulated security breach can teach you a lot about how your systems operate. The knowledge gained here will be invaluable to the IT team moving forward.


Many people cannot fathom how severe a security breach can get. They view it as a distant problem in the news, one that happens to other people. Pen testing can open the eyes of employees who do not take cyber attacks seriously.

Get Pen Testing with Cybriant

Pen testing is the gold standard of security evaluation for any company. With the help of white hat hackers, you can simulate a cyber attack on your organization. The information gathered in this exercise can speak volumes about your security posture–and how to strengthen it.

Cybriant provides white-labeled, managed security services to organizations of all kinds. We perform pen testing as well. Take a look at our services and prepare your organization for cyber attacks.

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