The Ultimate Manual To Penetration Testing

In today’s day and age, no business or person is immune to the threat of a hack or data breach. That’s why every company needs to assess its IT infrastructure and prioritize data security. Penetration testing is one of many ways that can help you identify vulnerabilities in your system.

What is Penetration Testing Anyway?

Penetration tests—also known simply as pen tests—evaluate the security of IT infrastructures by exploiting potential vulnerabilities.

Let’s say you wanted to determine how safe your house is from robbery or an intruder. So you try to break into your own home to see if your security system has any vulnerabilities, like loose window locks, camera blind spots, or broken motion sensors. Based on these points of weakness, you’d make the necessary adjustments to beef up security.

Penetration testing holds the same concept, except instead of checking locks and doors, you’re checking components of your IT infrastructure.

These assessments can find security gaps in operating systems, applications, configurations, user behavior, and more. The tests use manual or automated technology to intentionally compromise network devices, system endpoints, web apps, servers, and other areas where an IT infrastructure could be exposed to a hack or data breach.

How Penetration Testing Works

Pen testing is an ethical simulation of a security breach. Your data and network aren’t actually at risk during the simulation.

Penetration testing can be accomplished manually or by using automated technology to perform the simulation. This process ensures that real data won’t be lost during the test.

There’s much more to a penetration test than the simulated breach itself. The process can be segmented into several different stages:

  • Planning and preparation
  • Discovery and reconnaissance
  • Gaining and maintaining access
  • Analysis and reporting
  • Remediation
  • Retesting

First, testers need to determine the goals of the pen test. You need to figure out what tools and testing methods will be used to achieve these goals, which we’ll discuss in greater detail later on.

As the process continues, the testing team will do some additional research and recon on the target of the simulation. This could be anything from IP addresses to firewalls, endpoint connections, names, job titles, phone numbers, and other data of value.

Once the testers have the information they need about the target, the actual penetration attempt must happen. Testers will try to see exactly how deep they can penetrate the network to learn how exposed the system is to potential threats.

After the test is run, reports will be generated on the entire process. The reports should contain details on each step taken to penetrate the network and what security weaknesses were discovered in the simulation. Many reports will also include remediation advice.

Finally, the IT team needs to beef up the weaknesses discovered in the simulated breach. To ensure that the vulnerabilities were fixed, you should run another pen test to see if the changes actually worked.

Penetration Testing vs. Vulnerability Scanning

Pen tests are commonly associated with vulnerability scans, as both terms are used for IT infrastructure security. That said, penetration tests and vulnerability scans are very different.

Vulnerability scanning leverages technology to examine an IT environment automatically. Then the scanners generate a report that identifies vulnerabilities and other known weaknesses.

While a vulnerability scan can definitely provide valuable insights into security flaws in an IT system, these scans don’t go as deep as pen tests. Penetration testing takes a vulnerability scan one step further by seeing if potential exposed areas can be used to gain access within a system.

Penetration tests also account for the unique circumstances of each IT environment, and they help IT teams prioritize remediation based on areas with the greatest risk.

Manual Penetration Testing vs. Automated Penetration Testing

We’ll discuss different pen testing methods in greater detail later on, but all methods can be segmented into two categories—manual and automated.

As the name implies, a manual penetration test is conducted by a real person (or people) to simulate a hack. It’s crucial to have someone who is an expert to realistically simulate an attack scenario. Otherwise, the pen testers may not uncover all potential vulnerabilities.

Automated tools work well for teams that lack experience in pen testing. They’re easy to run and require minimal human intervention.

Manual tests take much longer to run than automated tests, but automated tests are more likely to yield false positives. With a manual test, the tester needs to generate a report on their own. Reports will be generated for you if you’re using an automated pen-testing tool.

Many organizations use a combination of both manual and automated tests. Automated pen testing works well when you have a large number of targets, and manual testing works well for highly specific, complex targets that can’t be performed with a tool alone.

Pen Testing vs. (Red) Teaming

“Teaming” or “red teaming” are two terms commonly associated with penetration testing.

As the risk of hacks and data breaches becomes more prominent, teaming exercises are used to take penetration tests to the next level.

The concept behind teaming is simple—teams are split into two groups, with one attacking and the other defending. Red teams are tasked with identifying vulnerabilities and penetrating the system. Blue teams need to defend against the attacks in real-time.

These exercises can be extremely helpful to train your staff to act quickly in the event that your firewalls and security systems get breached by a hacker.

Example 1: Network Service Testing

Network service testing is one of the most common examples of a pen test. The purpose here is to discover security gaps and vulnerabilities within the network infrastructure.

Since networks can have internal and external access points, these tests must be run locally on the client side and remotely from an external access point.

For a network service test, it’s common for pen testers to target things like:

  • Firewall configurations
  • IPS deception
  • DNS level attacks
  • Switching and route-based testing
  • Network databases like SQL servers
  • SMTP mail servers
  • Misc. network parameters

Misconfigured assets or even weak passwords can be used to gain access in a network service test.

Example 2: Wireless Network Testing

The purpose of a wireless network test is to assess the vulnerabilities of client-side wireless devices that are deployed on a network. Endpoints include laptops, tablets, smartphones, and anything else connected to the wireless network.

In addition to the devices, penetration testers will also target wireless configuration protocols and access points for wireless setups.

Example 3: Web Application Testing

As organizations rely heavily on web apps for daily tasks, this example has become very common in the world of pen testing.

In addition to the apps themselves, you’ll also need to target plugins, browsers, endpoints, and other application components that users would use to interact with the application.

Coding errors, authentication issues, injunction vulnerabilities, and authentication problems are all examples of things that could be uncovered during a web app penetration test.

How to Get Started With Penetration Testing

The idea of breaching your own IT infrastructure for security purposes can be a bit intimidating, especially if you’ve never been through this process before. To help you get started, we’ve broken down the tactical steps required to have success with penetration testing.

Step 1: Identify Your Goals and Targets

Your IT infrastructure is complicated. Rather than targeting the entire system at one time, pen tests work much better if you start with one area before moving on to another.

It usually makes sense to start by running tests on systems with the most sensitive data or the systems that would cause the biggest fallout in the event of a hack or data loss.

Your goals could also be tied directly to maintaining certain levels of compliance.

For example, your company might need to follow regulations set forth by GDPR, HIPAA, Sarbanes-Oxley (SOX), PCI DSS, CMMC, and more.

Suppose your company handles patient records and medical data in the healthcare industry. In that case, you can start by running pen tests on systems that contain this sensitive information to ensure your compliance with HIPAA regulations.

In this scenario, any endpoints or servers where patient records can be accessed would be the primary focus of the pen test. Web apps that aren’t used for patient records wouldn’t necessarily be a top priority unless those apps could give hackers access to other areas of your network.

Step 2: Assemble Your Testers

Next, you need to figure out who will be running the pen tests. Start by consulting with your IT security team. See if they have the expertise and resources to run these successfully on their own.

Remember, pen testing can be conducted manually or by using automated tools. So if your team doesn’t have the expertise required to run pen tests, they can always use automated technology to their advantage.

Alternatively, you can work with third-party cybersecurity firms to try and breach your system with a pen test.

“Teaming” exercises (mentioned earlier) are another combination to consider here as you’re assembling testers. In this scenario, the testers will be split into two teams—one team will attempt to breach the weak points of your IT infrastructure while the other team will take steps to defend it.

Step 3: Choose Your Penetration Testing Methods

Based on your goals established in step one, and your team assembled in step two, you need to select a penetration testing method that will achieve whatever you’re trying to accomplish.

Common pen testing methods include:

  • External Penetration Testing — External tests target organizational assets that are visible on the open web. Things like your website, email, web applications, domain name servers, etc., all fall into this category. The goal for testers here is to penetrate the system through an external access point and extract sensitive data.
  • Internal Penetration Testing — This approach simulates an attack by an insider with malicious intent. Scenarios could include rogue employees or a hack on employee credentials that were compromised during a phishing attack.
  • Targeted Penetration Testing — As the name implies, targeted tests are designed for something specific. This could be a specific data set, like customer information, or a particular area of your IT infrastructure, like your firewall configurations. Targeted tests are useful for seeing how your system holds up from the attacker’s point of view.
  • Blind Penetration Testing — With blind tests, the tester is only provided with the name of the organization being targeted. They have full control over how they’ll try to breach the system and look for vulnerabilities. This method works best if the tester isn’t associated with your company.
  • Double-Blind Penetration Testing — Double-blind tests are the best way to simulate a real-world breach or hack. Your security team won’t be given any prior knowledge of the simulated attack, so they won’t have time to prepare and beef up defense systems before the breach.

You can always run a combination of these tests at different times. Each one has its benefits in the world of data security.

But it’s always best to pick the methods that align with your primary goals.

Step 4: Analyze, Remediate, and Repeat

Regardless of the method you’ve used, you’ll need to take time and review the reports from the test. These reports will provide valuable insight into your system and show you exactly how a hacker could penetrate your IT infrastructure.

In some scenarios, you might learn that the tester could get past the first line of defense but was unable to breach your system further.

While this would be great news, as your data would remain protected, you’d still need to focus on fixing that first line of defense that was vulnerable during the breach.

Repeat your penetration test after you’ve fixed the problem. You might ultimately decide to use different methods the next time around. But the goal here is to ensure the fixes actually worked.

Then you can move on and continue running additional pen tests on different areas of your IT infrastructure.

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Bryan Wise
Bryan Wise,
Former VP of IT at GitLab

Incredible companies use Nira