Penetration testing, or “pen testing,” is a vital cybersecurity practice that simulates cyberattacks to uncover system vulnerabilities. By identifying and addressing security weaknesses before malicious actors can exploit them, your organization can better protect sensitive data, maintain customer trust and maintain regulatory compliance. Penetration tests are essential to prevent costly breaches and strengthen overall security posture.  

How to do penetration testing – A step-by-step approach to strengthening your cybersecurity 

In this article, we’ll walk you through the penetration testing process by using BPM’s methodology as a framework to explain how to conduct effective pen tests. 

1. Scoping and planning: The foundation of effective penetration testing 

The first step in any penetration test is thorough scoping and planning. This phase sets the stage for the entire process. It’s not about following a rigid template. Instead, it’s about tailoring the approach to each unique environment. To successfully execute this step, we suggest the following process: 

• Clearly define your security goals. What are you trying to protect? What are your main concerns? This helps focus the test on areas that matter most to your organization. 
• Develop a detailed testing plan. This should outline the specific type of pen test you’ll conduct. Will it be a black box test where testers have no prior knowledge of the system? Or a white box test with full system information provided? Perhaps a gray box test that falls somewhere in between? 
• Choose the tools you’ll use carefully. There’s a wide range of pen testing software available. Select ones that align with your goals and target systems. Remember, the most expensive tools aren’t always the best fit for your needs. 
• Establish clear boundaries for the test. Determine which systems are in scope and which are off-limits. This prevents unintended disruptions to critical operations. It also keeps the test focused and efficient. 

2. Reconnaissance and information gathering: Mapping the attack surface   

With a plan in place, the next step is reconnaissance. This step is about collecting as much relevant information as possible about your organization and employees. It simulates what a real attacker would do before launching their assault. 

OSNIT

We suggest that you start with open-source intelligence (OSINT) gathering. This involves collecting publicly available information about your organization. It might include data from websites, social media profiles or public records. 

Potential entry points

Be sure to look for potential entry points. These could be outdated software versions, misconfigured servers or exposed employee information. Each piece of data helps build a picture of the organization’s attack surface. 

Network mapping

Network mapping can identify active IP addresses, open ports and running services. This information will guide the later stages of the pen test as it helps testers understand where to focus their efforts. 

Remember, thoroughness is key in this stage. The more complete your reconnaissance, the more effective your later testing efforts will be. 

3. Vulnerability scanning and analysis: Uncovering weaknesses  

With a map of the target environment, it’s time to start actively probing for vulnerabilities. This step combines automated scanning tools with manual analysis techniques. 

You will need to begin with automated vulnerability scanners. These tools can help you quickly identify known vulnerabilities across a wide range of systems and applications. They’re excellent for finding common misconfigurations or outdated software versions. 

Automated tools can miss context-specific vulnerabilities or produce false positives, so don’t rely solely on them. Manual analysis is available to dig deeper, verifying scanner results and looking for unique weaknesses. 

Be sure to also assess your existing security controls. The firewalls, intrusion detection systems and access controls you have in place all play a role. Understanding these defenses helps you plan potential exploit attempts. 

Analyze all findings carefully, keeping in mind that not all vulnerabilities are equally critical. You’ll want to prioritize based on potential impact and ease of exploitation. This helps focus your remediation efforts where they’ll have the most significant effect. 

4. Exploitation and post-exploitation: Putting vulnerabilities to the test 

During the exploitation phase, pen testers attempt to leverage discovered vulnerabilities, simulating what a real attacker would do to gain unauthorized access to your systems or data. 

Exploitation 

Start with the most critical vulnerabilities that you identified earlier. Attempt to bypass security controls and gain initial access to your target systems. This might involve exploiting software bugs, misconfigurations or weak passwords. 

Post-exploitation

If your exploitations are successful, move into post-exploitation activities. This includes attempts to escalate privileges, move laterally through your network or exfiltrate sensitive data. The goal is to understand the full potential impact of a successful breach. 

Best practices for this step

Throughout this phase, be sure to document all successful and unsuccessful attempts. Note which vulnerabilities led to compromises and how far an attacker could potentially go, as this information is crucial for your final report. 

It’s important that you conduct this phase ethically and safely. Always stay within the agreed-upon scope and avoid any actions that could cause system outages or data loss. The aim is to demonstrate risks, not create new ones. 

5. Reporting and remediation guidance: Turning insights into action 

The final and perhaps most crucial phase is reporting. This is where all your findings are compiled into a clear, actionable document. Here is how we recommend that you structure your report: 

Executive summary

It’s important to start with an executive summary. Keep these points in mind when crafting it:  

• Provide a high-level overview of your test results.  
• Highlight key findings and their potential impact on your organization.  
• Use clear language that non-technical stakeholders can easily understand. 

Body of the report

In the main body of the report, detail each vulnerability you found. Explain how it was discovered and exploited, while providing clear evidence, such as screenshots or log entries. This helps your organization understand and verify each issue. 

Most importantly, you’ll want to offer specific remediation guidance. Don’t just point out problems – provide clear solutions. It’s best to include technical details for IT teams to act on. This might involve the following: 

• Configuration changes 
• Patch recommendations 
• Coding fixes 

Teaming up with cybersecurity specialists 

While understanding the penetration testing process is valuable, executing it effectively requires specialized skills and experience. This is where collaborating with cybersecurity specialists, like BPM, becomes crucial. 

• Expertise: Professional penetration testers bring a wealth of knowledge to the table. They stay updated on the latest threats, vulnerabilities and testing techniques, helping ensure your pen test is thorough and aligned with current best practices. 
• Access to advanced resources: Specialists also have access to advanced tools and methodologies. These resources may be too costly or complex for many organizations to maintain in-house. By leveraging knowledge from a cyber professional, you benefit from state-of-the-art testing capabilities. 
• Unbiased perspective: External specialists can identify blind spots that internal teams might overlook. This fresh viewpoint is invaluable for uncovering hidden vulnerabilities.  
• Customized approaches: Cybersecurity firms like BPM adapt their methods to your specific industry, regulatory requirements and risk profile. This customization supports you in getting the most relevant and impactful results from your pen test. 
• Result interpretation and remediation planning: Working with these specialists also helps in interpreting results and planning remediation. They can provide context for findings, prioritize risks and offer practical advice for improvements. This guidance is crucial for translating test results into effective security enhancements. 
• Maximize value: By collaborating with cybersecurity specialists, organizations can get the most from their penetration testing efforts. It’s an investment in expertise that pays dividends in stronger, more resilient security postures. 

Strengthen your cybersecurity through regular penetration testing 

Penetration testing is not a one-time event. It’s an ongoing process that should be repeated regularly. As systems change and new threats emerge, continuous testing is essential. 

By following this comprehensive approach to penetration testing, organizations can significantly enhance their security posture. They can identify and address vulnerabilities before malicious actors exploit them. 

Remember, the goal of pen testing is not to achieve perfect security – that’s an impossible target. Instead, it’s about continuously improving your defenses, staying ahead of threats and minimizing risks to your valuable digital assets. 

Partner with BPM for penetration testing 

Ready to take your cybersecurity to the next level? BPM’s experienced team can provide the unbiased perspective and customized approach you need. We’ll help guide you through the complexities of penetration testing and turn insights into actionable security improvements. 

Don’t leave your cybersecurity to chance. Reach out to BPM today to discuss how our Penetration Testing Services can fortify your defenses and give you peace of mind.