Pen Test Life Cycle: How To Triumph

Introduction

Even if you have every cybersecurity solution under the sun to protect your business, there will ALWAYS be a way into your business.

Vulnerabilities lurk everywhere in your cybersecurity – and most you wouldn’t even think of.

That’s where a penetration tester, also known as a pen tester or ethical hacker, comes in.

Pen testers push your cybersecurity solutions to the limits just like a real hacker would. They will enter your business like that of a hacker in the way that they take advantage of any vulnerability to get into your connected systems.

But what is the pen test life cycle? What is the process that pen testers will take with your business and your cybersecurity solutions?

And, how can you pass the penetration test? We’ve put together a quick analysis of what pen testers will do to your business, and how you can triumph over one.

Pen Test Life Cycle: The Planning Phase

Before you start your Pen Test, you first need to plan what you are hoping to gain out of it. Only then can you understand what you need to do to triumph.

To plan the pen test, you need to:

Define Objectives and Scope

The first step in the pen test life cycle is to define clear objectives and scope for the assessment. This involves identifying the specific goals that the penetration testing aims to achieve.

Some examples of the objectives your business may take are:

• To evaluate the effectiveness of your security controls.
• Identify the vulnerabilities in your critical systems.
• Test the resilience of your organisation’s overall security posture.

Defining the scope of your penetration test helps you determine the boundaries and limitations of the testing process.

It outlines the systems, applications, and networks that will be included in the assessment, as well as any exclusions or constraints. Clearly defining objectives and scope ensures that the pen tester and your organization have a shared understanding of what will be assessed. This will allow you to have a focused and efficient testing process.

Identifying Target Systems and Applications

In the pen test life cycle, identifying target systems and applications is a crucial task.

It involves selecting the specific systems and applications that will be tested for vulnerabilities and weaknesses. The selection is based on factors such as the criticality to your business, the exposure to any potential threats, and the systems’ importance to your organisation’s operations.

By identifying the target systems and applications, the pen tester can prioritize their efforts and allocate resources effectively to the most important parts of your business.

This step also includes understanding the connections between all your different systems and applications, as compromising one system may lead to gaining access to other connected systems.

Gathering Information

Gathering information is a fundamental step in the pen test life cycle. It involves collecting relevant data and details about the target environment, systems, applications, and network infrastructure.

This information-gathering phase can be both passive and active. Passive information gathering involves researching publicly available information, such as conducting open-source intelligence (OSINT) activities, analyzing public documents, or exploring social media profiles to gain insights into the organization’s technology stack.

Whereas active information gathering includes techniques like network scanning, service enumeration, and vulnerability scanning to identify potential entry points and vulnerabilities.

Pen Test Life Cycle: The Reconnaissance Phase

The reconnaissance phase is a critical component of the pen test life cycle, as it involves gathering valuable information about the target systems and applications. This phase is for the pen tester to gather insights and intelligence which can be used to identify any potential vulnerabilities and weaknesses in your business.

This stage lays the groundwork for the next few stages of the penetration test that will take place.

Passive Information Gathering

Passive information-gathering techniques in the pen test life cycle involve collecting data without direct interactions with the targetted systems.

This passive information gathering can include:

• • Analyzing publicly available information.
  • Browsing websites.
  • Reviewing documentation.
  • Monitoring social media platforms.

This helps the pen tester gain a better understanding of the target organization, its employees, the technologies in use, and the potential security risks whilst minimising the risks of their detection – an important part of the pen test life cycle.

Active Information Gathering

Active information-gathering techniques in the pen test life cycle involve direct interaction with your target systems and applications.

This can include:

• • Network scanning to identify live hosts.
  • Port scanning to discover open ports.
  • Service enumeration to gather information about running services.

By actively probing the target systems, the pen tester can gather more detailed and real-time information, allowing for a more accurate assessment of the organisation’s security posture.

Vulnerability Scanning and Analysis

Vulnerability scanning and analysis play a crucial role in the pen test life cycle.

It involves the pen tester using specialized tools to scan the target systems and applications for known vulnerabilities. The scanning process can identify:

• • Weaknesses in system configurations.
  • Outdated software versions.
  • Known security vulnerabilities.

Once the vulnerabilities are identified, they are analyzed to determine their potential impact and exploitability. This helps the pen tester to prioritise vulnerabilities based on their severity and enables them to focus on those with the highest risk to your organisation.

Pen Test Life Cycle: Scanning and Enumeration Phase

The scanning and enumeration phase involves actively probing any of the identified target systems and applications to gather information about their configuration and vulnerabilities.

This phase focuses on identifying open ports, discovering services running on those ports, and mapping the target network architecture.

Port Scanning

Port scanning is an important technique used in the pen test life cycle to identify open ports on your target systems. It involves sending ‘network packets’ to the target and attempting to establish connections with various ports. It shows which ports are open, closed or filtered.

Port scanning helps in mapping the network and identifying potential entry points that can be targeted for further analysis and exploitation.

Service Enumeration

Service enumeration is the process of gathering detailed information about the services running on the target system. It involves actively interacting with the open ports identified and extracting the relevant information such as service banners, version numbers, and configurations.

This helps the pen tester understand the specific software and protocols in use.

By obtaining detailed information about the services, the pen tester can determine the appropriate attack vectors and methods for further exploitation.

System Identification

System identification is a vital aspect of the scanning and enumeration phase in the pen test life cycle. It involves mapping the target network architecture and identifying individual systems within the network.

System identification provides a comprehensive understanding of the target network’s structure, allowing the pen tester to focus their efforts on specific systems or areas that may be more vulnerable to exploitation.

This information is crucial for planning and executing further stages of the penetration testing process effectively.

Pen Test Life Cycle: Exploitation Phase

The pen test life cycle exploitation phase involves leveraging identified vulnerabilities to gain unauthorized access to the target systems.

This phase is where the pen tester actively attempts to exploit weaknesses in the target environment, demonstrating the potential impact an attacker could have if those vulnerabilities were to be exploited maliciously.

Exploiting Vulnerabilities

Exploiting vulnerabilities is a core component of the pen test life cycle’s exploitation phase.

After identifying specific vulnerabilities, the pen tester utilizes various techniques, tools, and exploits to exploit these weaknesses. This can include leveraging software vulnerabilities, misconfigurations, or weaknesses in the target system’s defences.

By successfully exploiting vulnerabilities, the pen tester demonstrates the potential consequences of these security weaknesses and provides concrete evidence to support the need for remediation and mitigation efforts.

Gaining Access to Systems

Once vulnerabilities have been successfully exploited, the pen tester moves on to accessing the target systems unauthorised. This typically is done by bypassing or circumventing authentication mechanisms, gaining control over user accounts, or exploiting privileges to gain entry into restricted areas.

Gaining access to systems allows the pen tester to:

• • Further explore the target environment.
  • Gather sensitive information.
  • Assess the potential impact an attacker could have if they were to infiltrate the organization’s systems.

Escalating Privileges

In the escalation of privileges phase, the pen tester aims to elevate their level of access within the compromised systems. This involves acquiring higher-level privileges, such as administrative or root access, which grants the pen tester more control and broader access within the target environment.

Privilege escalation techniques can include exploiting:

• • Misconfigurations
  • Weak access controls
  • Vulnerabilities within the system itself.

By escalating privileges, the pen tester demonstrates the potential for an attacker to gain extensive control over the compromised systems and emphasizes the importance of robust privilege management and access control mechanisms.

Overall, this stage highlights the potential impact of vulnerabilities and emphasizes the need for proactive security measures to prevent unauthorized access within your organisation’s systems.

Pen Test Life Cycle: Post-Exploitation Phase

The post-exploitation phase in the pen test life cycle occurs after the successful compromise of a system and involves various activities aimed at maintaining access, covering tracks, and exploring further within the target environment.

Maintaining Access

This is where the pen tester aims to ensure they maintain their unauthorised access to the compromised system or network without being detected. To do this, the pen tester must establish persistence by setting up backdoors, creating hidden user accounts, or deploying remote access tools.

By maintaining access, the pen tester can continue to explore the target environment, gather additional information, and assess the potential extent of damage an attacker could cause if they were to retain access undetected.

Covering Tracks

An essential aspect of the post-exploitation phase for a pen tester is for them to cover their tracks. Covering their tracks involves erasing or hiding evidence of penetration testing activities.

The pen tester will try to remove any traces that could lead to your organisation identifying their unauthorised access. This can include deleting log files, modifying timestamps, altering system logs, or removing any indicators of unauthorized access.

Covering tracks helps maintain the integrity of the assessment and allows the organization to focus on addressing the identified vulnerabilities rather than investigating the testing itself.

Pivoting to Other Systems

Pivoting to other systems is a technique employed in the post-exploitation phase of the pen test life cycle, allowing the pen tester to expand their reach within the target environment.

Once access is gained to a compromised system, the pen tester explores potential pathways and vulnerabilities that could lead to other systems within the network.

Pivoting to other systems enables the identification of additional security weaknesses, and highlights the importance of implementing robust network segmentation and access controls to prevent unauthorized access to your organisation’s systems.

Summary

By maintaining access and covering their tracks effectively, pen testers are able to demonstrate the potential impact an attacker could have if they were to maintain undetected access to critical systems.

Pen Test Life Cycle: Reporting Phase

The reporting phase is a crucial stage in the pen test life cycle, where the pen tester documents the findings, recommendations, and actions taken during the assessment.

Documenting Findings and Recommendations

In the pen test life cycle, documenting findings and recommendations is a key aspect of the reporting phase. The pen tester should carefully record and document all the vulnerabilities, weaknesses, and security issues found during the assessment.

This includes:

• • Providing a detailed description of each vulnerability.
  • Its potential impact.
  • The steps required to remediate or mitigate the identified risks.

Additionally, the pen tester should offer recommendations for improving your organisation’s overall security posture based on their assessment findings.

Thorough documentation of findings and recommendations will help your organisation understand any vulnerabilities found so that you can take appropriate actions to enhance your security defences.

Presenting the Report to Stakeholders

This stage is where the pen tester communicates the assessment findings, recommendations, and overall results to relevant stakeholders, such as management (you), your IT teams, and any other key decision-makers.

They should also ensure the report can be understood by both technical and non-technical decision-makers.

The presentation of the report is an opportunity for the pen testers to highlight the significance of the identified vulnerabilities and the importance of addressing them promptly to ensure your organisation’s security to protect valuable assets.

Follow-up Actions

The follow-up actions in the reporting phase of the pen test life cycle involve you collaborating with all stakeholders to implement the recommended remediation measures.

This includes discussing and prioritizing:

• • The identified vulnerabilities based on their severity.
  • The potential impact.
  • The feasibility of mitigation.

It is crucial to establish a clear roadmap for addressing the identified issues and assigning responsibilities to the relevant teams or individuals. Regular communication and coordination among stakeholders are necessary to ensure that the recommended actions are implemented effectively and within the desired timeframe.

Follow-up actions aim to close the identified security gaps, strengthen defences, and reduce the organization’s risk exposure.

Summary

In conclusion, the reporting phase of the pen test life cycle involves documenting the findings and recommendations, presenting the report to stakeholders, and taking follow-up actions to address the identified vulnerabilities.

The comprehensive report serves as an IT roadmap that your organization can use to enhance its security posture and make informed decisions to mitigate risks.

Effective communication and collaboration among stakeholders is essential to ensure that the recommended actions are carried out and the organization’s security is improved as a result.

Tips To Pass Pen Test

Preparing for and successfully passing a pen test requires a combination of technical expertise, effective communication, and a methodical approach.

Here are some key tips to excel in the pen test life cycle:

Understand the Purpose:

Before thinking about how to pass a penetration test, it’s essential to first understand its purpose.

A pen test is conducted to identify vulnerabilities and weaknesses in your business’s security systems. Recognize that the goal is not to pass or fail but rather to uncover areas that require improvement. This mindset shift will help you approach the test constructively.

Hire a Reputable Penetration Testing Team:

Engaging a reputable and experienced pen tester is crucial.

Look for professionals who hold industry certifications and have a track record of successful assessments. They should be well-versed in the latest attack techniques and possess a deep understanding of security best practices.

Provide Adequate Information:

To ensure an effective penetration test, it’s important to provide your testing team with comprehensive information about your systems, networks, and applications. Share network diagrams, documentation, access credentials, and any relevant security policies.

This enables the testers to simulate real-world attack scenarios and identify potential vulnerabilities accurately.

Define Clear Objectives:

Clearly define the objectives and scope of the penetration test in collaboration with your testing team. Determine which systems and applications will be targeted, and outline any specific compliance requirements or regulations the pen tester should consider during the assessment.

This helps to focus the testing efforts and ensures that the areas of highest concern are adequately evaluated.

Regularly Patch and Update Systems:

Keeping your systems up to date with the latest security patches and software updates is critical.

Penetration testers often exploit known vulnerabilities to assess your defences. By regularly patching and updating your systems, you can minimize the chances of successful attacks during the test.

Perform Vulnerability Scanning:

Before undergoing a penetration test, consider conducting vulnerability scanning. This automated process identifies common vulnerabilities and misconfigurations in your systems.

By addressing these issues proactively, you can minimize potential risks and provide a more secure environment for the penetration testers to assess.

Address Previously Identified Issues:

If your business has previously undergone a penetration test and vulnerabilities were identified, make sure to address and remediate those issues before the next assessment.

This demonstrates a commitment to improving your security posture and can lead to a more successful test outcome.

Learn from the Test Results:

Once the penetration test is complete, carefully review the findings and recommendations provided by the testing team.

Treat the test as a valuable learning opportunity. Prioritize the identified vulnerabilities based on severity, and develop an action plan to address them. Regularly assess and reassess your security practices to ensure continuous improvement.

Conclusion

In conclusion, to pass the pen test, focus on preparation and knowledge enhancement, emphasize effective communication and collaboration, and maintain attention to detail with a methodical approach.

By continuously improving your technical skills, fostering good communication, and meticulously conducting the assessment, you’ll be better equipped to navigate the complexities of the pen test life cycle and achieve successful results.

Contact Us

The ins and outs of cybersecurity can be confusing and difficult to deal with as a business owner.

If you need advice on your cybersecurity and how to create an advanced cybersecurity posture for your business, contact us here at Jera.

We have over 20 years of experience in IT Support and IT security and would be more than happy to have a chat about your business’s cybersecurity.

Or alternatively, learn more about your cybersecurity and pen tests with Jera’s cybersecurity courses online. Contact us to learn more.