An advanced penetration testing methodology should be comprehensive and follow a structured approach. Here is a detailed methodology focusing on the reconnaissance phase, along with a checklist for each step.
- Passive Reconnaissance:
Passive reconnaissance involves collecting information about the target without directly engaging or interacting with the target systems. This phase is essential to gain a better understanding of the target and its environment.
Checklist:
- Identify the target organization’s public presence (websites, social media accounts, news articles, etc.)
- Gather information on employees (names, roles, email addresses, etc.) from sources like LinkedIn or data leaks
- Enumerate domain names and subdomains using tools like DNSDumpster, crt.sh, and sublist3r
- Analyze DNS records (A, AAAA, MX, NS, TXT, etc.) using online tools or dig command
- Identify IP address ranges and ASN information using services like ARIN or RIPE
- Collect open-source intelligence (OSINT) using tools like theHarvester, recon-ng, or Maltego
- Search for any known vulnerabilities or breaches related to the target organization
- Active Reconnaissance:
Active reconnaissance involves direct interaction with the target systems to gather more information about them. This phase helps to identify potential attack vectors and vulnerabilities.
Checklist:
- Perform network scanning to identify live hosts using tools like Nmap, Masscan, or Zmap
- Enumerate open ports and running services on the target hosts with Nmap or similar tools
- Fingerprint the operating systems and services using Nmap’s OS and version detection or tools like p0f
- Enumerate network shares, user accounts, and other information using SMB enumeration tools like SMBMap or enum4linux
- Enumerate web applications and directories using tools like Dirbuster, Gobuster, or ffuf
- Identify web application technologies using tools like Wappalyzer or BuiltWith
- Perform SSL/TLS analysis using tools like SSLyze or TestSSL.sh to identify potential vulnerabilities or misconfigurations
- Enumerate SNMP information, if applicable, using tools like snmpwalk or snmp-check
- Active Directory Reconnaissance (for internal pen testing):
In an internal penetration test, enumerating Active Directory (AD) information is essential to understanding the target environment, identifying potential attack paths, and planning further attacks.
Checklist:
- Enumerate domain information (domain controllers, domain functional level, etc.) using tools like net or PowerShell commands
- Enumerate user accounts, groups, and organizational units (OUs) using tools like ADExplorer, BloodHound, or PowerShell commands
- Enumerate group memberships and identify high-privileged accounts (e.g., Domain Admins, Enterprise Admins)
- Identify potentially interesting accounts or groups (e.g., Backup Operators, service accounts)
- Enumerate computer accounts and identify potentially interesting systems (e.g., servers, workstations with sensitive data)
- Enumerate Group Policy Objects (GPOs) and analyze them for potential misconfigurations or vulnerabilities
- Enumerate trust relationships between domains, if applicable
By following this methodology and checklist, you will have a comprehensive understanding of the target environment, which will help you plan and execute further penetration testing activities effectively. Remember to always conduct penetration tests ethically and with proper authorization.
