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Penetration Testing Basics: Your First Steps into Ethical Hacking

Jason J. Boderebe
4 min read
#penetration-testing #ethical-hacking #cybersecurity #security-testing

Penetration Testing Basics: Your First Steps into Ethical Hacking

Penetration testing is one of the most exciting and challenging fields in cybersecurity. It combines technical skills, creative thinking, and ethical responsibility to help organizations strengthen their security posture.

What is Penetration Testing?

Penetration testing, often called “pen testing” or “ethical hacking,” is the practice of testing a computer system, network, or web application to find security vulnerabilities that an attacker could exploit. Unlike malicious hackers, penetration testers work with explicit permission to help organizations identify and fix security weaknesses.

Core Phases of Penetration Testing

1. Reconnaissance

The first phase involves gathering information about the target system. This includes:

  • Passive reconnaissance: Collecting publicly available information
  • Active reconnaissance: Directly interacting with the target system
  • Social engineering: Gathering information through human interaction

2. Scanning and Enumeration

Once you have initial information, the next step is to:

  • Identify live systems and open ports
  • Determine services running on those ports
  • Enumerate system details and potential entry points

3. Gaining Access

This phase involves:

  • Exploiting identified vulnerabilities
  • Gaining initial access to systems
  • Escalating privileges when possible

4. Maintaining Access

  • Installing backdoors or persistence mechanisms
  • Ensuring continued access for further testing
  • Documenting access methods

5. Covering Tracks

  • Removing evidence of the penetration test
  • Cleaning up any files or changes made
  • Ensuring system stability

Essential Tools for Beginners

Network Scanning

  • Nmap: The gold standard for network discovery and port scanning
  • Masscan: High-speed port scanner for large networks
  • Zmap: Internet-wide network scanner

Vulnerability Assessment

  • Nessus: Comprehensive vulnerability scanner
  • OpenVAS: Open-source vulnerability assessment tool
  • Nikto: Web server scanner

Exploitation Frameworks

  • Metasploit: The most popular exploitation framework
  • Cobalt Strike: Commercial penetration testing platform
  • Empire: Post-exploitation framework

Web Application Testing

  • Burp Suite: Comprehensive web application security testing platform
  • OWASP ZAP: Free web application security scanner
  • SQLmap: Automated SQL injection testing tool

Setting Up Your First Lab

Virtual Environment

  1. VMware Workstation or VirtualBox for virtualization
  2. Kali Linux as your primary testing distribution
  3. Metasploitable as a vulnerable target system
  4. DVWA (Damn Vulnerable Web Application) for web app testing

Network Setup

  • Create an isolated network for your lab
  • Use NAT or host-only networking to prevent accidental external access
  • Document your lab network topology

Always Remember:

  • Written Permission: Never test systems without explicit written authorization
  • Scope Definition: Clearly define what systems and techniques are allowed
  • Data Protection: Handle any discovered data with extreme care
  • Responsible Disclosure: Report vulnerabilities through proper channels

Professional Certifications

  • CEH (Certified Ethical Hacker): Entry-level certification
  • OSCP (Offensive Security Certified Professional): Hands-on practical certification
  • GPEN (GIAC Penetration Tester): Advanced penetration testing certification

Common Vulnerabilities to Practice

OWASP Top 10

  1. Injection flaws (SQL, NoSQL, OS commands)
  2. Broken authentication and session management
  3. Sensitive data exposure
  4. XML External Entities (XXE)
  5. Broken access control
  6. Security misconfigurations
  7. Cross-Site Scripting (XSS)
  8. Insecure deserialization
  9. Using components with known vulnerabilities
  10. Insufficient logging and monitoring

Building Your Methodology

Develop a Consistent Approach

  1. Pre-engagement: Define scope, rules of engagement, and objectives
  2. Intelligence Gathering: Collect information about the target
  3. Threat Modeling: Identify potential attack vectors
  4. Vulnerability Analysis: Identify and prioritize vulnerabilities
  5. Exploitation: Attempt to exploit identified vulnerabilities
  6. Post-Exploitation: Determine the impact of successful exploits
  7. Reporting: Document findings and provide remediation recommendations

Next Steps

Continuous Learning

  • Practice on legal platforms like HackTheBox, TryHackMe, and VulnHub
  • Join cybersecurity communities and forums
  • Attend security conferences and workshops
  • Stay updated with the latest security research and vulnerabilities

Career Paths

  • Internal Penetration Tester: Working for a single organization
  • Consultant: Working for a security consulting firm
  • Bug Bounty Hunter: Finding vulnerabilities for rewards
  • Red Team Member: Simulating advanced persistent threats

Conclusion

Penetration testing is a field that requires continuous learning and ethical responsibility. Start with the basics, practice in legal environments, and always remember that the goal is to improve security, not to cause harm.

The journey from beginner to expert penetration tester is challenging but rewarding. Focus on building a strong foundation in networking, operating systems, and security concepts before diving into advanced exploitation techniques.

Always test ethically and legally - only on systems you own or have explicit written permission to test. The cybersecurity community thrives on trust and responsible disclosure.

Ready to start your penetration testing journey? Check out our HomeLab setup guide to build your own testing environment.