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Penetration testing simulates an attack on your networks, systems, or applications to identify weaknesses in your security infrastructure.

Setting up a secure network or program is a process that takes time and effort. Organizations need to stress test their systems to maintain their security posture. In some cases, that can come down to a few automated scans. But to see where you really stand on risk prevention, you need to implement penetration testing. 

During penetration tests, a tester (sometimes called an ethical hacker) attempts to breach your systems. These pen tests help you find vulnerabilities you can only see from the outside looking in.

Below, we cover how a pen test works, the various types available, and how to perform one. 

What Is Penetration Testing?

A penetration test is a simulated attack against your company's systems and networks to uncover weaknesses and vulnerabilities. Pen testers use the same tools, techniques, and processes that attackers use to find flaws in a system. As such, pen tests can simulate different types of attacks and attacks on different targets.

Penetration testing involves:

• Manual and automated activities

• Trained security experts familiar with the systems they’re testing

• Hiring a third party to conduct the test or creating an internal team

• Relatively high costs to conduct

A penetration test reveals the kinds of attacks you can withstand and which ones you can't. If you find vulnerabilities during the pen test, you can use that information to fortify and patch weaknesses within your systems. Remember that pen tests usually hone in on specific aspects of a system, so be sure to clearly define your penetration testing scope and avoid focusing on too many targets at once. 

What Can You Perform Penetration Tests On?

Unlike automated security scans, which only report on known, high-level vulnerabilities, pen tests reveal how a hacker would actually detect and exploit weaknesses. Pen testers glean in-depth insights by narrowing their focus to one system, network, or app at a time. Specifically, you can carry out the pen testing process on:

• Web applications: Pen testers can find coding errors, authorization issues, and injection risks on your apps. Testers should also review security controls to anticipate web attack patterns. 

• Mobile apps: Testers should see how your servers interact with mobile app users. They can find session management risks, authentication problems, and cryptographic risks.

• Networks: Network pen tests reveal weak spots leading to your systems and customer data. Pen testers often focus on encrypted transport protocols, SSL scoping, and test cases for admin services.

• Cloud environments: Unlike on-site storage, cloud deployment invites risk from your organization and the cloud service provider. Pen tests should review all parties’ cloud configurations, storage, databases, and security controls.

• Databases: Many hackers see database access as their ultimate goal. Pen tests ensure that only authorized individuals can access your database and make plans in case a data breach occurs. 

• Embedded devices (IoT): Pen testers can find vulnerabilities between embedded devices. Misconfiguration between devices poses a high risk, so pen tests minimize weaknesses and keep your IoT ecosystem safe.

• Continuous integration/Continuous delivery (CI/CD) pipeline: CI/CD pipeline relies on automation for code scanning and security. A manual pen test can find hidden vulnerabilities in your pipeline. 

• Application program interfaces (APIs): APIs present risks when broken object-level authorization, data exposure, and rate-limiting issues go unaddressed. Pen tests identify these vulnerabilities before breaches occur.

Some businesses also run social engineering penetration tests. Many data breaches occur as a result of phishing attacks and fraud. By simulating these attacks, you can gauge how well your staff withholds valuable information. You can also diversify your approach by asking testers to reach staff via email and phone. 

Penetration Testing vs. Vulnerability Scanning

Pen tests and vulnerability scanning both point out weaknesses in networks, systems, or applications. That said, pricing varies between the two methods, and they don’t offer the same level of detail. Compared to penetration testing, vulnerability scans:

• Rely more on automation than manual tests

• Cost less and take less time to complete

• Look at the big picture instead of focusing on parts of a system

• Must run continuously to keep up with new systems added to networks and create a measurable baseline for your security posture

Vulnerability scanning can help find security weaknesses. However, it doesn’t paint a vivid picture of what causes those weaknesses or their full impact in the way pen tests do. 

Why Pen Testing Is Important

Penetration tests are important because they use the same techniques as an outside hacker to point out risks before breaches occur. Even if a system has no flaws, the tests build confidence in its security and highlight strengths. 

The main benefits of penetration testing include:

• Identifying and prioritizing security vulnerabilities

• Increasing confidence in your current security posture

• Noting security budget priorities

• Improving staff awareness of security protocols

• Evaluating incident response plans

• Meeting regulatory compliance with frameworks like PCI DSS, which requires penetration testing once a year or after changes to the environment, and quarterly vulnerability scans

Common Penetration Testing Methods

Different teams may prefer one approach to penetration testing over another. Each method varies based on:

• The amount of information given to hackers before a test 

• If an organization knows when a test will occur

 We’ll explain the different testing methods below.

Black Box Penetration Testing

A black box pen test (sometimes called an external pen test) gives the tester little to no background on your infrastructure, networks, systems, or applications. This type of pen testing simulates a real-world cyberattack, with the pen tester taking on the role of an outside hacker. 

Since black box testing requires little to no prior knowledge about the system or network being tested, this type of pen test is best carried out by an outside firm. 

White Box Penetration Testing

A white box pen test (also known as an internal pen test) requires a pen tester to have prior knowledge of your source code and environment. This context allows white box tests to provide more detail than a black box pen test would. The tester also has more leverage to exploit your systems. 

 This type of pen testing typically gives companies a full examination of their:

• Applications

• Systems

• Networks

• Cloud configurations

• Source code

Gray Box Penetration Testing

A gray box pen test gives the tester partial knowledge or access to an internal network or web app. This type of pen test helps organizations see what an attack would look like if:

• A hacker gains access to some company information 

• A hacker doesn’t have a roadmap of your network and system information

Knowing what information to provide takes a careful understanding of your security setup. Try to balance providing information an outside hacker could find without giving too much away. 

Red Team/Blue Team Exercises (Purple Teaming)

Red team/blue team testing, sometimes called purple teaming, improves security with real-time feedback between two teams. On one side, you have a red team of offensive security professionals trying to breach a system; on the other, a blue team of security staff trying to stop them. 

This approach simulates a real-time security breach. By sharing feedback between teams, your staff can learn about new threats and react in real-time. Not only does this help find new vulnerabilities, but purple teaming also teaches staff to communicate under duress. 

Covert Pen Testing

In a covert pen test (also known as a double-blind pen test), almost no one in the company knows that the pen test will occur—including the IT and security professionals who will respond to the attack. This type of test measures your incident response plan in the face of what looks like a real data breach. 

5 Stages of Penetration Testing

Simulating an outside attack takes careful planning. To ensure your test prepares you for real threats, follow these four penetration testing steps.

1. Scoping

Before starting a pen test, your stakeholders and hackers need to write a pre-engagement contract. This document boils down to your rules of engagement and sets the scope of your test. It also gives managers and their teams a chance to note their testing priorities, timeframes, and methods. 

By having all parties sign the form, you have legal proof the test received approval. For the pen tester, this gives them legal protection after hacking into the client’s systems. 

2. Reconnaissance

Penetration tests and real data breaches begin with reconnaissance. Organizations pick a penetration tester and the systems to focus on and handle any planning concerns during this phase. From there, you’ll choose the type of test you want to run and share information about your IT infrastructure accordingly. 

After aligning on the scope of the test, your pen tester will gather information on their target from internal and external sources. In addition to the details they’re given, testers will research vulnerabilities independently via:

• Internet searches

• Domain registration retrieval

• Known application vulnerabilities

• Network scanning

• Social engineering

3. Penetration Attempt 

After researching your system, testers will start attempting to exploit it. Ultimately, they want to demonstrate how far into your environment they can go. You’ll also want to see what an outside hacker can do with your system, including:

• Deleting, changing, or stealing an organization’s private data

• Transferring company funds into other accounts

• Copying customer account information

• Damaging a company’s reputation via social media logins or web copy changes

4. Reporting

After accessing your network, testers will gather data while attempting to penetrate your system. They will place it into a report highlighting how they infiltrated your system, security weaknesses, and how to remediate those vulnerabilities. 

Have the tester pay special attention to:

• Specific weaknesses they exploited

• The tools they needed to exploit those vulnerabilities

• The data they could and couldn’t access with this approach

• The amount of time your tester remained undetected

• The most significant hurdles they had to contend with

• Any security measures that didn’t deter them at all

5. Re-Testing

You’ll then review the tester’s findings and update your system. After you implement the recommendations from the pen tester to fortify your environment, consider hiring the same pen tester to re-test your environment. With this approach, you can confirm that you adequately addressed their findings.

Companies should re-test their systems regularly to achieve compliance with some frameworks. For example, PCI requires two penetration tests a year or after making major changes to your environment. Major changes include OS changes, new firewall software, or moving data to the cloud. 

Penetration Testing Best Practices

To make the most of each penetration test, follow these best practices. 

• Clearly define your objectives: Lay out your scope and goals before a test. Decide what you want to test, why you want to test it, and how you'll respond to results before defining a budget.

• Go beyond minimum requirements: Different compliance frameworks set baseline test requirements. Don't treat these requirements as your goal—use them as a baseline. Take every precaution to protect your data with testing.

• Find the most qualified testers: Conducting a pen test takes expertise. Consider outsourcing your test if your internal teams can't find every possible breach.

• Monitor your systems: Before a pen test starts, monitor your internal systems to gauge the tester's skill and your network's durability. Going in with a baseline will also help you measure the results. 

• Set communication guidelines: Let relevant personnel know when a test will occur and give them time to prepare. Additionally, set aside time to discuss the test's results with your team. 

• Go beyond the results: Your work isn't over after a pen test ends. Consider each vulnerability's risk level and potential outcomes if a breach occurs. From there, create a prioritized plan to patch up your weak spots.

Penetration Testing FAQ

You may still have questions on how to do penetration testing. To help you along, we’ll answer some frequently asked questions on the entire penetration testing process.

What Penetration Testing Tools Can You Use?

The best penetration tests lean on specialized tools, not an all-in-one program. These tools can help with specific functions like app scanning or finding breach points. In general, you can expect to use five types of cybersecurity tools during pen tests: 

• Recon tools: Explore networks and look for open ports.

• Proxy tools: Create gateways between hackers and their targets.

• Vulnerability scanners: Uncover weaknesses in networks, applications, and APIs.

• Exploitation tools: Locate access points within systems that lead to assets.

• Post-exploitation tools: Expand a hacker’s access to systems after the initial breach.

Who Should Conduct Your Penetration Test?

The staff best suited to a pen test depends on your resources and the type of test you want to run. Hiring an outside contractor makes the most sense if you want to run a test without giving the tester prior knowledge. Since they will look at your system from the outside, this method reflects real-life hacking scenarios. On the other hand, tests where you give the hacker system information suit internal staff. That said, you should only leave it to internal staffers if you’re confident in their abilities. If there’s a chance they’ll miss any blind spots, another round of testing or one conducted by an outside firm could be beneficial.

What Happens After a Penetration Test?

Once the pen test ends, your tester will share their findings with your organization. Specifically, they will share:

• Security vulnerabilities

• Suggestions for improving risk prevention

• Validation and sanitization approaches

• The documentation of how they conducted their tests

With this information, you can create an action plan for improving your cybersecurity. Remember to share the test results with your IT and compliance staff to plan your next steps. 

How Drata Can Help You Ensure Ongoing Security and Compliance

In the end, penetration testing is a small part of a robust security and compliance strategy. It serves as a great starting point for testing the security strength of a system or network. And because it’s required by common frameworks like PCI, folding regular pen tests into your process will help you achieve and maintain compliance. 

Need a hand staying on top of your compliance to-do list? Drata can help. 

Our tools automate testing processes and monitor your network for any signs of threats. Additionally, our in-house experts can let you know when it’s time for your next penetration test and identify risks to your data.