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Server Penetration Testing Roadmap

G5 Cyber Security

TL;DR

This guide provides a structured approach to server penetration testing, covering reconnaissance, scanning, exploitation, post-exploitation, and reporting. It’s designed for both beginners and those looking to refine their methodology.

1. Planning & Scope Definition

  1. Define the scope: Clearly identify which servers are in scope. Get written permission!
  2. Rules of Engagement (ROE): Document acceptable testing methods, prohibited activities (e.g., denial-of-service), and contact information for emergencies.
  3. Gather Information: Collect server names, IP addresses, operating systems (if known), network diagrams, and any publicly available documentation.

2. Reconnaissance

Passive information gathering without directly interacting with the target servers.

  1. DNS Enumeration: Use tools like nslookup or online DNS records lookups to find subdomains and associated IP addresses. 
    nslookup example.com
  2. WHOIS Lookup: Identify the owner, contact information, and registration details of the domain. 
    whois example.com
  3. Search Engines (Google Dorking): Use advanced search operators to find sensitive information exposed online.
    Example: site:example.com filetype:pdf
  4. Social Media & Public Repositories: Search for employee names, technologies used, and potential vulnerabilities mentioned publicly.

3. Scanning

Active information gathering to identify open ports, services, and potential vulnerabilities.

  1. Port Scanning (Nmap): Discover open ports and running services. 
    nmap -sV -T4 -A
  2. Service Version Detection: Identify the versions of running services to pinpoint known vulnerabilities. Nmap’s -sV flag is useful for this.
  3. Vulnerability Scanning (Nessus, OpenVAS): Use automated vulnerability scanners to identify potential weaknesses.
    • Configure scans appropriately based on the target environment.
    • Review scan results carefully; false positives are common.

4. Exploitation

Attempting to gain access to the server using identified vulnerabilities.

  1. Exploit Research: Search for publicly available exploits on platforms like Exploit-DB or Metasploit.
    • Match exploits to the specific versions of running services.
  2. Metasploit Framework: A powerful framework for developing and executing exploits. 
    msfconsole
  3. Manual Exploitation: If an exploit isn’t readily available, consider manual exploitation techniques based on the vulnerability.
  4. Web Application Testing (if applicable): Test for common web vulnerabilities like SQL injection, cross-site scripting (XSS), and remote file inclusion (RFI).

5. Post-Exploitation

Actions taken after gaining access to the server.

  1. Privilege Escalation: Attempt to gain higher privileges on the system.
    • Look for misconfigured services, kernel vulnerabilities, or weak passwords.
  2. Data Gathering: Collect sensitive information such as user accounts, passwords, and configuration files.
  3. Maintaining Access (Optional): Establish a persistent backdoor to maintain access (with permission!).

6. Reporting

Documenting the findings of the penetration test.

  1. Executive Summary: A high-level overview of the testing process and key findings for non-technical stakeholders.
  2. Technical Report: Detailed documentation of all identified vulnerabilities, exploitation steps, and remediation recommendations.
  3. Remediation Recommendations: Provide specific steps to fix identified vulnerabilities.
    • Prioritize vulnerabilities based on severity and impact.

Resources

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