14 Common Penetration Testing Challenges with Six Proven Tips For 2024

Penetration testing has become an essential security practice for businesses. While most businesses manage to do it effectively, there are some critical penetration testing challenges that they must be prepared to deal with to ensure maximum benefits from the tests. In this blog, we will look at fourteen common pentesting challenges and a few useful tips to handle them. 

Penetration testing is a planned attack  which  is performed on an organization’s computer systems to gauge its capacity to defend against threats. Unless an organization realizes its strengths and weaknesses, it is nearly impossible for it to take measures to address these threats. 

What Are the Common Pentesting Challenges?

Penetration testing challenges refer to the difficulties you face while performing penetration testing on your computer, network, or cloud infrastructure. Numerous types of challenges range from small to medium to complex. Ignoring these challenges will not only affect the efficiency of pen testing but also cause the emergence of newer challenges. Here are fourteen commonly reported penetration testing challenges. 

Common Pentesting Challenges e1708669067730

Limited access to tools and technology:

Lack of resources or limited access to them can result in inadequate testing, which affects the accuracy and effectiveness of the tests.

The scheduling struggle:

Most businesses can’t afford to schedule pen testing on their systems during working hours. Scheduling the tests thus becomes a big challenge. 

Legal and ethical consideration:

Pen testing has to be performed in compliance with the cyber security rules, regulations, and ethical standards prevalent in the  respective countries. This may restrict the use of certain testing methodologies and targets.

Complex network architectures:

If your organization has a complex network infrastructure, it may pose challenges to the pen testers in understanding or evaluating it correctly.

Consistency of testing:

Organizations are expected to ensure uniformity in the use of testing methods and criteria when they employ diverse assessments to bring reliability to the test results.

Evolving nature of cyberattacks:

 The nature of cyberattacks is constantly changing. This demands a greater amount of adaptability and flexibility in the testing approaches.

Generating accurate penetration testing reports:

Unless pen testers summarize the findings accurately and deliver them to their clients, it becomes impossible for organizations to take steps to thwart the attacks.

Weak assessment of encryption:

Sometimes, the pen testers fail to identify vulnerabilities in the encryption algorithms and take steps to address them, which might create challenges in data protection.

Limitation of resources:

 Lack of resources may result in inadequate testing and limit the chances of identifying  potential vulnerabilities.

Poor communication and collaboration:

Poor communication between testers and stakeholders will result in poor collaboration. This can potentially lead to a weak understanding of the critical issues and their solutions 

Insufficient employee knowledge:

An organization with employees who are not aware of security risks and protocols can intensify the chances of vulnerabilities. 

Black-box testing methods:

Black-box testing refers to testing without any prior knowledge of the systems. This can limit the accuracy of the testing and might not provide a thorough understanding.

Over-emphasizing severity:

Placing too much emphasis on high-severity vulnerabilities and overlooking other critical risks might not help with a thorough understanding of the vulnerabilities.

Overly Limited Scope:

Unless there is a broad set of testing parameters to prioritize, you won’t be able to identify vulnerabilities present in unexplored areas of the system. As a result, those areas will remain susceptible to threats. 

6 Proven Tips to Overcome Challenges in Penetration Testing

While these common challenges faced in penetration testing can have a serious impact on the efficiency of the test, there are several ways to tackle them. A comprehensive approach integrating strategic planning, proper communication and collaboration and up-to-date knowledge of the threats can boost the test’s effectiveness. Take a look at six effective tips to address common penetration challenges.

Common Pentesting Challenges 1 e1708670107328

Understand the scope of the test:

Before starting the test, make sure that there is clarity regarding the objectives, limitations, and boundaries of the test. This will help you ensure that the test is in alignment with organizational goals and avoid any chances of going beyond or shy of the scope.

Ensure transparent communication:

Through open, honest, and clear communication among all the stakeholders, you can ensure that there is better understanding, consensus and trust among all. This is critical for the success of the test.

Document and report every step:

Document and report each step involved in the test and the subsequent findings. This will help provide you with better chances for traceability and analysis of the test and findings and you can  use them for future reference.

Ensure legal and ethical compliance:

It is important to ensure the legitimacy and integrity of the testing process. For this, adhering to relevant laws, regulations, and ethical standards is essential.

Practice follow-up and remediation:

Once the vulnerabilities are identified, take steps to address them promptly. Implement fixes and monitor how effective they are. Check for any recurrences to maintain your sound security posture.

Invest in training and skill development:

Invest time and resources in the continuous education of your staff. If you have in-house pen testers, invest in enhancing their technical skills to keep pace with evolving threats and techniques.

author profile 1

Jim Jacob

Jim Jacob is the founder of Cyberguard. He is an IT professional who has 21 years of professional experience in the tech field. Cybergurad is the product of his vision to share the knowledge gained from his career through the power of words. He is an expert at explaining complex tech concepts in simple language and has written numerous articles on IT and Cybersecurity.

We Serve
Contact Us


    While these are common challenges in penetration testing, the type of challenge you may face in your organisation may vary depending on the nature and size of your computer systems. It’s important to be familiar with all possible challenges to take the right preventive measures when they emerge.

    Frequently Asked Questions

    Pentesting challenges are the challenges or obstacles faced during a scheduled pentesting activity. From lack of resources to poor communication, there are numerous challenges which can potentially impact the result of pentesting. 


    Reviewing past reports is one of the most effective ways to identify challenges in penetration testing. Additionally, stay updated on industry trends. If you encounter any challenge, do enough resources on it to explore its scope. 

    Both red teaming and penetration testing are part of the cybersecurity assessment procedure. Red teaming refers to the comprehensive procedure of performing simulated attacks. On the other hand, penetration testing is the evaluation of the security posture within an organization’s infrastructure – network, cloud, computer systems or whichever is specified before the test. 

    The most fundamental or basic pen testing challenges are those that you will need to address before even getting started. This includes defining the scope, communicating the gaps, assessing the technical complexities, and identifying the legal compliance requirements. 

    While conducting pen testing, it is important to stay prepared to address any potential hazards. For instance, system disruption, data loss, privacy breaches, legal implications, and reputational damage.

    Common limitations in pentesting include lack of time, tool limitations, resource availability, skill requirements, and the challenges of  simulating real-world scenarios accurately.