Penetration Testing

A penetration test, or pen test, is an attempt to evaluate the security of an IT infrastructure by safely trying to exploit vulnerabilities. These vulnerabilities may exist in operating systems, services and application flaws, improper configurations or risky end-user behavior. Such assessments are also useful in validating the efficacy of defensive mechanisms, as well as end-user adherence to security policies.

It might be helpful to think of penetration testing as trying to see if someone can break into your house by doing it yourself. Penetration testers, also known as ethical hackers, evaluate the security of IT infrastructures using a controlled environment to safely attack, identify, and exploit vulnerabilities. Instead of checking the windows and doors, they test servers, networks, web applications, mobile devices, and other potential entry points to find weaknesses.

Keep reading:

• Penetration Testing: Breaking in to Keep Others Out

One of the biggest hurdles in creating a successful cybersecurity program is finding people with the right qualifications and experience. The cybersecurity skills gap is well-documented issue with a qualified supply of security professionals not keeping up with demand. This is particularly true with pen testing. Unfortunately, there is no shortage of threat actors and cybercrime groups. Consequently, organizations can’t delay deploying critical pen testing initiatives.

But even with the skills gap, businesses can build a strong pen testing program by intelligently using the resources that are readily available because not every test requires an expert. Penetration testing tools that have automated features can be used by security team members who may not have an extensive pen testing background. These tools can be used for tests that are easy to run, but essential to perform regularly, like validating vulnerability scans, network information gathering, privilege escalation, or phishing simulations.

Of course, expert pen testers are still a critical part of pen testing. For complex tests that require delving deep into different systems and applications, or running exercises with multiple attack chains, you’ll want a person or team with more experience. In order to test a realistic attack scenario, you’ll want a red team that uses sophisticated strategies and solutions similar to threat actor techniques.  

Keep reading:

• How To Manage the Pen Testing Skills Shortage
• 3 Reasons Every Organization Should Leverage Third-Party Pen Testers
   

Penetration testing should be performed on a regular basis to ensure more consistent IT and network security management. A pen-tester will reveal how newly discovered threats or emerging vulnerabilities may potentially be assailed by attackers. In addition to regularly scheduled analysis and assessments required by regulatory mandates, tests should also be run whenever: 

Going through the results of pen tests provides a great opportunity to discuss plans going forward and revisit your security posture overall. Seeing pen tests as a hoop to jump through and simply checking it off a list as “done” won’t improve your security stance. It’s important to plan time for a post-mortem to disseminate, discuss, and fully understand the findings. Additionally, relaying these results with actionable insights to decision makers within the organization will better emphasize the risk that these vulnerabilities pose, and the positive impact that remediation will have on the business. With review, evaluation, and leadership buy-in, pen test results can transform into action items for immediate improvements and takeaways that will help shape larger security strategies.

Keep reading:

• Three Action Items to Consider After Completing a Pen Test
   

Vulnerability scanners are automated tools that examine an environment, and upon completion, create a report of the vulnerabilities uncovered. These scanners often list these vulnerabilities using CVE identifiers that provide information on known weaknesses. Scanners can uncover thousands of vulnerabilities, so there may be enough severe vulnerabilities that further prioritization is needed. Additionally, these scores do not account for the circumstances of each individual IT environment. This is where penetration tests come in.

While vulnerability scans provide a valuable picture of what potential security weaknesses are present, penetration tests can add additional context by seeing if the vulnerabilities could be leveraged to gain access within your environment. Pen tests can also help prioritize remediation plans based on what poses the most risk.

Keep reading:

• Top 14 Vulnerability Scanners for Cybersecurity Professionals
• Better Together: How Pen Testing Helps Take Vulnerability Assessments to the Next Level
   

When it comes to white, black, or gray box testing, defining each style can fall into three categories. Each category depends on the initial information provided prior to the pen test itself.

• White Box Penetration Testing: White box pen testing shares the full network and system information with the pen tester. All credentials, mapping, system and network information are given to the pen tester to enable a pen tester to focus on exploiting a target without needing an outside attack methodology to gain initial entry, creating an assumed breach scenario. White box pen testing targets specific systems with multiple attack vectors with as little difficulty and interruption as possible. 
• Black Box Penetration Testing: Black box pen testing is the opposite of white box, in that zero information is shared with the pen tester. This requires a tester to perform reconnaissance. determine attack paths. This is considered an authentic external test, in which a pen tester would use the same methods an attacker would use to compromise security measures to gain initial access to a company’s systems and potentially pivoting throughout the environment.  This attack test requires the most time and resources since there is no prior knowledge of a company’s infrastructure. 
• Gray Box Penetration Testing: Gray box pen testing is a mix of white and black box attack methods.  Limited information is provided to testers, typically login credentials, but other privileged information is withheld. Gray box testing is useful when an organization would like to see what an attack would look like should a cybercriminal be able to acquire access information, however, they don’t have a roadmap of pertinent network and system information. Gray box testing allows a company to assume credentials have already been compromised, and doing so, what potential damage can be caused from this style of breach.  
   

Cybersecurity teams typically have to ensure that they are maintaining compliance with regulations like:

• HIPAA
• PCI DSS
• SOX
• NERC
• HEOA
• GDPR
• CMMC

By exploiting an organization’s infrastructure, pen testing can demonstrate exactly how an attacker could gain access to sensitive data. As attack strategies grow and evolve, periodic mandated testing makes certain that organizations can stay one step ahead by uncovering and fixing security weaknesses before they can be exploited. Additionally, for auditors, these tests can also verify that other mandated security measures are in place or working properly.

For instance, many of these regulations either imply or specifically require pen testing as a way to evaluate an organization’s security posture and adherence. Requirement 11.3 of the Payment Card Industry Data Security Standard (PCI DSS), for example, states that a comprehensive pen testing program must be implemented.

Keep reading:

• Penetration Testing for Regulatory Compliance
   

Attackers use tools in order to make their breach attempts more successful. The same is true for pen testers. Penetration testing software is intended for human augmentation, not replacement—they allow pen testers to focus on thinking outside the box by taking over tasks that take time, but not brain power. When it comes to pen testing, it’s never a choice between penetration testing tools vs. penetration testers. Instead, it’s a choice of what penetration tools will help a penetration tester most.  

Penetration testing is typically completed using a portfolio of tools that provide a variety of functionalities. Some are open source, while others are commercial. Some of these tools are the same as those used by threat actors, allowing for the exact replication of an attack. Others highlight the needs of an ethical hacker, allowing for a stronger emphasis on features that prioritize the end goal of validating security weaknesses without affecting production environments, and prioritizing remediation.  

Security teams are also turning to penetration testing tools to advance their in-house programs through strategic automation. Automation can elevate the skills of inexperienced testers with wizards that safely guide them through critical standard tests; experienced testers can maximize their time by automating the routines. 

So what should you look for when it comes to an automated pen testing solution? Penetration testing tools should be simple, efficient, reliable, and centralized.

Keep reading:

• The Human Element of Pen Testing and the Role Tools Can Play
• How Commercial Pen Testing Tools Can Make Your In-House Testing Program More Effective and Efficient
• Three Things You Need in a Penetration Testing Tool
   

Pen testing software and services are one of the top ways to evaluate an organization’s ability to secure networks, applications, endpoints, and users from exploitation of security weaknesses. However, depending on your circumstances, you may have to choose between software and services. Other times, you’ll need both. So how do you determine which approach you need? 

First, you’ll need to evaluate your company’s size and structure. If you have on-staff security analysts, perhaps automated tools are the best option. External pen testing services can give an outside perspective of your cybersecurity needs. The combination of both is the best way to ensure some of the strongest coverage. 

The guide When to Use Penetration Testing Software, Services, or Both gives detailed advice to help determine what level of pen testing your company needs, by examining pen testing scope, organization size and structure, tools and resources available, analyst skills and experience, and implementation timeline.
 

A common tactic of attackers trying to breach an environment is to use an exploit against a known vulnerability in an application or device present in a targeted infrastructure. Exploiting a vulnerability can provide an attacker with privileges or capabilities they would not normally be granted. In order to provide insight into what threat actors might be able to do, pen testers also use exploits.

Usually, attackers have to write exploits as they find vulnerabilities. Others are readily available on the internet, usually posted anonymously by other attackers.

On the ethical hacking side, exploit development can be an advanced penetration testing skill that takes time to master. Additionally, when on a job, pen testers often don’t have the resources to create a new exploit. Many resort to searching for and using pre-written exploits they find online—oftentimes the same ones attackers use.

Because exploit writing takes time and expertise, both attackers and pen testers alike are always looking for exploits or exploit libraries that can save them the effort. Access to enterprise exploit libraries are often a benefit that comes with owning an enterprise pen testing tool.

Keep reading:

• Open Source vs. Enterprise: Why NOt All Exploits are Created Equal