Penetration testing on a Windows operating system involves a systematic approach to identify, exploit, and document security vulnerabilities. The process typically follows a five-to-seven-phase methodology: Planning, Reconnaissance, Scanning, Exploitation, Post-Exploitation, and Reporting
1. Pre-Engagement and Planning
Before any technical action, define the scope and legal boundaries.
Define Scope: Identify which Windows systems (e.g., workstations, servers, Active Directory) are included.
Rules of Engagement (ROE): Establish timeframes, approved tools, and prohibited actions to avoid damaging production systems.
Legal Authorization: Obtain written consent to conduct testing.
2. Reconnaissance (Information Gathering)
Gather information about the target to identify potential entry points.
Passive Recon: Use open-source intelligence (OSINT) to find information without directly interacting with the target.
Active Recon: Use techniques like WHOIS lookup, DNS interrogation, and network mapping to identify target IP addresses and operating system versions.
3. Scanning and Enumeration
Identify open ports, services, and specific vulnerabilities on the Windows machine.
Port Scanning: Use Nmap to find open ports (e.g., 445 for SMB, 3389 for RDP).
Vulnerability Scanning: Use automated tools like Nessus or OpenVAS to identify missing patches or misconfigurations.
Enumeration: Perform deeper, manual probing to identify active user accounts, shared folders, and active directory structures.
4. Exploitation
Attempt to bypass security controls by exploiting identified vulnerabilities.
Exploit Frameworks: Use Metasploit to deploy exploits targeting vulnerabilities such as MS17–010 (EternalBlue).
Credential Attacks: Use tools like John the Ripper or Hashcat to crack weak passwords.
Client-Side Attacks: Use social engineering or malicious, crafted files
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Windows OS Penetration Testing Procedures at Vsasf Tech ICT Academy Enugu was originally published in Coinmonks on Medium, where people are continuing the conversation by highlighting and responding to this story.

