Penetration Testing Phases

OpenSploit's five-phase penetration testing methodology with automated phase transitions and tool recommendations.

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OpenSploit follows a structured penetration testing methodology with five phases. The agent automatically transitions between phases based on findings, though you can override this manually.

Phase Overview

Reconnaissance → Enumeration → Exploitation → Post-Exploitation → Reporting

1. Reconnaissance

Goal: Discover what’s running on the target

The first phase focuses on understanding the attack surface:

Port scanning (TCP/UDP)
Service detection and version identification
OS fingerprinting
Web technology detection

Key Tools:

nmap - Port scanning and service detection
web-fingerprint - Web technology identification
whatweb - Additional web fingerprinting

Example:

> Perform reconnaissance on 10.10.10.1

Running nmap full port scan...
Found open ports: 22/tcp (SSH), 80/tcp (HTTP), 443/tcp (HTTPS)
Detected OS: Linux (Ubuntu)
Web server: nginx 1.18.0

2. Enumeration

Goal: Gather detailed information about discovered services

With services identified, enumerate them deeply:

Directory and file discovery
Vulnerability scanning
Version-specific CVE research
Application mapping

Key Tools:

ffuf / gobuster - Directory bruteforcing
nikto - Web vulnerability scanning
nuclei - Template-based scanning
cve-lookup - CVE research

Example:

> Enumerate the web application on port 80

Running directory scan...
Found: /admin, /api, /uploads, /backup
Running nuclei vulnerability scan...
Found: CVE-2021-XXXXX in detected CMS

3. Exploitation

Goal: Gain initial access to the target

Attempt to exploit discovered vulnerabilities:

SQL injection testing
Credential attacks
Known vulnerability exploitation
Custom exploit execution

Key Tools:

sqlmap - SQL injection
hydra - Credential brute-forcing
metasploit - Exploitation framework
exploit-runner - Custom exploits

Example:

> Test the login form for SQL injection

Running sqlmap on /login endpoint...
Vulnerability found: time-based blind SQL injection
Extracting database schema...
Found credentials in users table

4. Post-Exploitation

Goal: Escalate privileges and maintain access

After gaining initial access:

Privilege escalation
Credential harvesting
Lateral movement
Persistence mechanisms

Key Tools:

privesc - Privilege escalation enumeration
ssh - Remote access
tunnel - Port forwarding and pivoting
mysql / mongodb - Database access

Example:

> I have SSH access as www-data. Escalate privileges.

Running privilege escalation checks...
Found: SUID binary /usr/bin/find
Exploiting via: find . -exec /bin/sh \; -quit
Gained root access

5. Reporting

Goal: Document findings and generate reports

Aggregate all findings into a professional report:

Finding categorization by severity
Evidence collection
Remediation recommendations
Multiple output formats

Output Formats:

Markdown
HTML
PDF (planned)

Severity Levels:

Critical - Immediate exploitation possible
High - Significant security impact
Medium - Moderate risk
Low - Minor issues
Info - Informational findings

Phase Transitions

OpenSploit automatically transitions phases based on:

Trigger	Transition
Ports/services discovered	Recon → Enumeration
Vulnerabilities identified	Enumeration → Exploitation
Initial access gained	Exploitation → Post-Exploitation
Objectives completed	Any → Reporting

Phase-Appropriate Tools

Each phase has recommended and discouraged tools:

Phase	Recommended	Discouraged
Reconnaissance	nmap, web-fingerprint	sqlmap, metasploit
Enumeration	ffuf, nuclei, nikto	exploitation tools
Exploitation	sqlmap, hydra	reconnaissance tools
Post-Exploitation	privesc, tunnel	scanning tools