A Comprehensive Guide to the Penetration Testing Process

Penetration testing is a cornerstone of cyber security, but it’s not a one-size-fits-all activity. It involves a series of stages, each one tailored to the requirements of the test and each playing a crucial role in ensuring the organisation's cyber defences are robust. There are various industry methods for conducting pen tests, however, this guide will specifically focus on a detailed exploration of the six-phase approach followed by our Red Team: planning, reconnaissance, scanning, vulnerability assessment, exploitation, and reporting. 

The Six Stages of Penetration Testing

1. Planning: Setting the Foundation

At the heart of any successful penetration test is a well-thought-out plan. This initial phase involves defining the scope, objectives, and parameters of the test, thus creating the roadmap for the entire process. This ensures the test aligns with the organisation's goals and objectives. A clear plan also helps establish the rules of engagement, including whether it's a black box, white box, or grey box test, which we’ll unpack in greater detail in our next post. 

2. Reconnaissance: Laying the Groundwork 

Reconnaissance, often referred to as the information-gathering phase, is a bit like scouting a battlefield before a strategic operation. Testers collect data about the ‘target’ to help them understand its infrastructure, systems, and potential vulnerabilities. This can be done using OSINT (Open-Source Intelligence), which is information available in the public domain. This information is scrutinised to answer specific intelligence questions, in this case, to find information that could be used to gain access to the system. This phase is critical in preparing a comprehensive strategy, allowing the penetration testers to mimic real-world scenarios with precision. 

3. Scanning: Identifying the Gaps 

Stage 1 and 2 lay the foundation, and stage 3 — scanning — involves the use of various tools and techniques to scan the organisation’s environment for vulnerabilities and weaknesses. The goal is to identify potential entry points or security gaps that can be exploited. By conducting thorough external and internal scans, the testers can gain insight into the network architecture, identify potential security flaws, and prioritise the areas that need further investigation.  

4. Vulnerability Assessment 

After identifying vulnerabilities, the penetration testers analyse and assess the severity and potential impact exploitation of the identified vulnerabilities would have on the organisation’s systems. This helps categorise the vulnerabilities and ensures penetration testers focus on the ones that pose the greatest risk. A thorough vulnerability assessment provides penetration testers with valuable insights into the organisation’s security posture and potential areas for improvement. 

5. Exploitation: Simulating Real Attacks

With a solid foundation and essential information, the penetration testers move on to the core of the operation — simulating real-world attacks. This stage can include social engineering attacks — such as phishing, smishing, or vishing — or more direct assaults. The focus is on gaining and importantly maintaining access, mimicking the persistence of sophisticated adversaries. The aim is to exploit any vulnerabilities discovered in the previous phase, and then compromise the target system to demonstrate impact as well as to highlight deficiencies in the organisation’s cyber security posture. 

6. Reporting: Dissecting the Findings

Once the simulated attacks have been executed, the final step in the process is reporting. Penetration testers dissect their findings, scrutinising the results of their endeavours. This involves a meticulous examination of vulnerabilities, compromised systems, and potential points of failure. The reporting phase is where the real value of penetration testing emerges, providing organisations with actionable insights into their security posture and recommendations for remediation of identified vulnerabilities. 

Remediation: Strengthening Defences  

Armed with the insights gained during reporting, organisations can implement fixes to address the identified vulnerabilities and fortify their defences. Remediation is more than patching specific issues; it's a strategic move toward an enhanced cyber security posture. This stage also involves a feedback loop, where lessons learnt from the test are applied to continuously improve security measures. As part of the process, the remediation team will prioritise the uncovered vulnerabilities, identifying those most likely to happen as well as those that will have the most severe impact on business. Remediation of these vulnerabilities can then either be done by an external provider or by an in-house team and there are pros and cons to both approaches.  If you want to know more about cyber security vulnerability remediation, you can download this handy guide: 

Things to consider when deciding on a remediation approach: 

• Hybrid Approach: Some organisations adopt a hybrid model, combining the strengths of external specialist providers and in-house teams for a balanced and effective remediation strategy. 
• Training and Skill Development: Investing in training programmes for in-house teams can enhance their skills, making them more adept at handling complex cyber security challenges, but these skills development interventions can be costly — both in terms of the time taken to acquire the certifications and the cost thereof.  
• Clear Communication: Whether relying on external specialists or an in-house team, a clear and open channel of communication between the IT department, management, and other relevant stakeholders is crucial for an efficient remediation process. 

In our next post, we’ll take a look at the different types of penetration testing — black box, white box, and grey box testing — and unpack the pros and cons of each. 

At Cyberlogic, we offer a comprehensive suite of cyber security solutions, which includes penetration testing, vulnerability management, and remediation solutions. To find out more, visit the Security Solutions page on our website or reach out to us at hello@cyberlogic.co.za.  

Read the previous post in the series.