How to be a Better Penetration Tester

Penetration testing is a crucial security practice for organizations of all sizes. It primarily involves finding, exploiting and remedying existing cybersecurity vulnerabilities in an organization’s network, systems, applications and data. Becoming an effective penetration tester requires a mix of technical and conceptual skills in order to successfully identify, analyze and test security flaws.

What is a Penetration Tester?

A penetration tester is a security professional who works with organizations to find, test and help fix security issues in their IT systems on an ongoing basis. Penetration testers are typically employed or contracted by organizations to identify potential security issues before they become an active threat. Usually, penetration testers have intense knowledge of different computer networks and information systems and can use specialized tools to detect any potential vulnerabilities or weaknesses that can be exploited.

Penetration testers use a variety of techniques to identify and exploit security vulnerabilities. These techniques include manual testing, automated testing, and social engineering. Manual testing involves the tester manually inspecting the system for potential vulnerabilities. Automated testing involves the use of automated tools to scan the system for potential vulnerabilities. Social engineering involves the tester attempting to gain access to the system by exploiting the human element of the system.

Technical Skills for Penetration Testing

To become a successful penetration tester, having a strong knowledge of different computer networks, servers, firewalls, web applications and system components is essential. As a penetration tester, it is also important to be familiar with different operating systems such as Linux, Mac OS X, Windows and BSD, as well as various scripting languages like Python, Bash, Go, or Ruby. Additionally, it is beneficial to understand how commonly used protocols like TCP/IP and HTTP work.

In addition to the technical skills, penetration testers should have a good understanding of security principles and best practices. This includes knowledge of encryption algorithms, authentication protocols, and secure coding practices. It is also important to have a good understanding of the different types of attacks that can be used to exploit vulnerabilities in systems and networks. Finally, it is beneficial to have experience with different security tools and frameworks, such as Metasploit, Nmap, and Burp Suite.

What Tools Do Penetration Testers Use?

Penetration testers typically use a combination of open source and commercial security tools to better understand the target system’s infrastructure and its potential vulnerabilities. Open source tools such as Nmap, Nessus and Metasploit are commonly used for reconnaissance and vulnerability detection, while commercial tools usually provide more advanced functionality such as automated vulnerability assessment.

In addition to these tools, penetration testers may also use specialized hardware and software to gain access to the target system. This could include physical access devices such as lock picks, or software-based tools such as password crackers. The goal of these tools is to gain access to the system and identify any potential vulnerabilities that could be exploited.

Understanding Network Infrastructure

Penetration testers need to understand different network infrastructure elements such as routers, switches, firewalls and WAPs, as well as the protocols involved (e.g. TCP/IP and DNS). Additionally, being knowledgeable about security measures such as Access Control Lists (ACLs), Virtual Private Networks (VPNs) and Intrusion Detection Systems (IDS) will increase the effectiveness of security tests.

It is also important for penetration testers to understand the different types of attacks that can be used to exploit vulnerabilities in a network infrastructure. Common attack types include Denial of Service (DoS), Distributed Denial of Service (DDoS), SQL injection, Cross-Site Scripting (XSS), and Man-in-the-Middle (MITM). By understanding these attack types, penetration testers can better identify potential weaknesses in a network and develop strategies to mitigate them.

Learn the Principles of Ethical Hacking

For penetration testers, understanding ethical hacking principles is essential in order to perform their job successfully. Ethical hacking is the process of attempting to penetrate networks or individual computers in order to evaluate the security posture of a given system by identifying potential weaknesses before malicious hackers can exploit them. It is important for penetration testers to maintain a professional stance and adhere to ethical guidelines when conducting security tests.

Understand Different Types of Security Testing

Security testing entails various subtypes such as vulnerability assessment, web application testing and network penetration testing. Vulnerability assessments involve identifying weaknesses in the system that could potentially be exploited by unauthorized parties. Web application testing looks for untested inputs or flaws in web-related applications such as APIs or SQL servers. Network penetration tests attempt to access various parts of the target system using different methods.

Exploit Frameworks and Techniques

Penetration testers might need to take advantage of popular exploit frameworks such as Metasploit or Kali Linux in order to test different security scenarios. For example, Metasploit can be used to assess network infrastructure such as firewalls, routers and web servers for possible vulnerabilities. Additionally, understanding popular exploitation techniques such as cross-site scripting or buffer overflow attacks is necessary in order to identify potential flaws in a system.

Stay Up-to-Date with Security Trends

For any security specialist, staying current with recent security trends is essential. Penetration testers need to understand the latest threats that can emerge from newly found software vulnerabilities. Keeping up with these developments will help penetration testers assess systems more accurately and capture breaches that may not have been detected before with traditional methods.

Developing Reporting Skills

After performing several tests on a system, one of the most important areas of penetration testing is creating accurate reports. Reports need to include an overview of all tests performed on a system along with any identified weaknesses or potential security issues that can be exploited. In addition, it is important to include advice on how to remediate vulnerabilities in order to protect against malicious attacks. It's not enough to own a system, you must provide mitigation information and ways to prevent future attacks.

Professional Certifications

Many people choose to pursue professional certifications within the penetration testing industry. Certifications demonstrate your knowledge in the field and can be advantageous when searching for employment as a penetration tester. The OffSec Certified Professional (OSCP) is a common penetration testing certification companies want to see. Yet the Practical Network Penetration Tester (PNPT) is more highly regarded in the industry and allows for a better overall learning experience. If you're just getting started, the eLearnSecurity Junior Penetration Tester v2 (eJPTv2) is a great introduction to penetration testing.

Additional certs to consider might include the CREST Registered Penetration Tester or the SANS GIAC Cloud Penetration Tester (GCPN) or the SANS GIAC Penetration Tester (GPEN) or even the CompTIA Pentest+ which is great certification for managers and leaders of penetration testing teams that do not need the hands-on skills.

Plenty of other options are available too, including certifying in the tools themselves like the Kali Linux Certified Professional (KLCP) or the OffSec macOS Researcher (OSMR) certification. And once you get your first penetration testing role, you will likely want to continue your learning with more advanced certifications like the eLearnSecurity Certified Penetration Tester eXtreme (eCPTX) or the OffSec Certified Expert 3 (OSCE3) and others. There's far too many certifications to list and no perfect certification to achieve. So, choose what works best for you and your goals as a penetration tester.

Network with Other Professionals

Networking is always beneficial for any type of career field, but it is especially true for penetration testing. Networking with other professionals in the field can provide great opportunities for advancement through sharing information and ideas. There are many online forums, groups and conferences dedicated specifically to penetration testing which can be invaluable when trying to learn more about the field.

How to Find Penetration Testing Jobs

As penetration testing becomes more mainstream and important to organizations, more jobs have been created within the industry. It is possible to find penetration testing jobs through job listing sites such as Indeed or LinkedIn or by contacting specific organizations directly. Additionally, networking can provide great insight into potential job opportunities in the field.

What to Expect as a Penetration Tester

Most penetration testing jobs require extensive working knowledge of networking principles, web application technologies such as HTML, CSS and JavaScript as well as scripting skills. It is also necessary to be able to identify potential security risks by utilizing different tools and techniques. Additionally, being able to interpret data from logs and reports efficiently is important for proper security testing. Working as a penetration tester can often require long hours due to the complexity of some networks but it can also be an enjoyable experience when successful exploits are uncovered.

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