AdPentestAI-Python

Active Directory penetration testing framework with automatic Domain Controller detection.

Features

• Auto DC Detection — discovers Domain Controllers via DNS SRV records, LDAP RootDSE probes, and port fingerprinting
• Subnet expansion — scans /24 first, widens to /23 if no DC found
• Domain auto-discovery — extracts domain name from LDAP RootDSE defaultNamingContext
• DC FQDN resolution — multi-source FQDN lookup with live LDAP probe fallback, forward DNS verification
• DC-aware tool execution — passes discovered domain, DC IP, and FQDN to tools
• 29 AD/SMB/Kerberos/ADCS/Email tools — 12 cross-platform binaries + 3 Windows-native PowerShell + 3 Kerberos attack + 4 ADCS certificate attacks + 5 Email protocol enumeration
• SMB pentesting — null session detection, share enumeration, SMB signing detection, credential testing
• Windows-native tools — built-in PowerShell enumeration for LDAP, SMB, and AD forest discovery (no external dependencies on Windows)
• Cross-platform — runs on Linux, macOS, and Windows with platform-specific optimizations
• Auto-install — missing tools installed automatically via apt/pip/git (or native on Windows)
• Safety — dry-run is the default; --scope-confirmed required for authorization

DC Detection Strategies

1. DNS SRV — queries _ldap._tcp.dc._msdcs.<domain>, _kerberos._tcp.dc._msdcs.<domain>, etc.
2. LDAP RootDSE — anonymous bind to extract domain, forest level, hostname
3. Port fingerprint — checks Kerberos (88), LDAP (389/636), Global Catalog (3268/3269)
4. Subnet sweep — Kerberos port 88 quick-scan on /24, expands to /23, then /22 if no DCs found

SMB Pentesting Capabilities

• Null session detection — checks if targets allow anonymous SMB access (IPC$)
• Share enumeration — discovers available SMB shares via CrackMapExec and smbmap
• SMB signing detection — identifies if SMB message signing is enforced (via nmap scripts)
• Credential testing — attempts connection with guest/empty credentials via impacket tools
• Secretsdump — extracts NTLM hashes and session keys when null credentials work
• PsExec simulation — tests command execution capability via impacket psexec

Kerberos/Kerberoasting Attack Vectors

• GetUserSPNs — enumerates service principal names (SPN) via LDAP (custom implementation, no impacket needed)
• AS-REP Roasting — targets accounts with DONT_REQUIRE_PREAUTH flag for offline cracking
• Kerberoasting — extracts and cracks service account tickets via TGS-REQ requests
• Requires: null/guest credentials or valid domain account (LDAP access for SPN enumeration)
• Output formats: .txt files compatible with Hashcat/John for cracking
• Implementation: Pure Python LDAP-based tools (ldap3, no external binaries)

ADCS Certificate Attack Vectors

• Shadow Credentials — exploits ADCS to inject shadow credentials for account takeover via certificate-based authentication
• ESC1 — template misconfiguration allowing client authentication without enrollment agent
• ESC3 — enrollment agent misconfig enabling privilege escalation via certificate requests
• ESC9 — object control abuse via ADCS certificate manipulation
• Tools: Certipy-AD automated enumeration and exploitation
• Attack chain: certificate enumeration → template analysis → credential extraction → privilege escalation

Windows-Native Tools

PowerShell enumeration (built-in, no external dependencies on Windows):

• powershell_ldap_enum — LDAP RootDSE queries via .NET DirectoryServices
• powershell_smb_enum — SMB share enumeration via Get-SmbShare
• powershell_ad_recon — Forest/domain/DC discovery via AD API

Python-based Enumeration Engines:

• enum_windows_py — Pure Python enum4linux-ng replacement (LDAP + SMB + policy enumeration)

  • Null session detection and exploitation
  • Domain policy extraction (password complexity, lockout settings)
  • SMB share discovery via impacket
  • Works on Windows, Linux, macOS
  • Uses ldap3 + impacket (already required dependencies)

• SPNEnumerator — Custom LDAP-based Service Principal Name enumeration

  • Direct LDAP queries to extract SPNs without impacket.examples.GetUserSPNs
  • Anonymous LDAP bind capability
  • Hashcat/John compatible output format
  • Pure Python implementation (ldap3 only)

Cross-platform Tools:

• 12 binary tools (nmap, masscan, crackmapexec, smbmap, bloodhound, etc.)
• All tools auto-install via apt/pip/git based on platform

Email Protocol Enumeration & Credential Testing

Pure Python email enumeration (no external dependencies):

• SMTP User Enumeration — Discover valid email addresses via:

  • SMTP VRFY command (traditional user discovery)
  • SMTP RCPT TO validation (validate recipient addresses)
  • Service banner detection (Exchange/Postfix/Sendmail identification)
  • Ports: 25 (plain), 465 (SMTPS), 587 (SMTP TLS)

• Credential Testing with Protocol Fallback — Automatic fallback chain:

  • Primary: SMTP AUTH (ports 25, 465, 587)
  • Fallback: POP3 AUTH (ports 110, 995)
  • Fallback: IMAP AUTH (ports 143, 993)
  • Tests multiple credentials until success or all protocols exhausted
  • Supports TLS/SSL connections for secure ports

• Email Service Detection — Identify email infrastructure:

  • Exchange on-premises (2016, 2019, 2021)
  • Office 365 cloud detection (outlook.office365.com routing)
  • Server banner parsing and version detection
  • Concurrent port scanning for email services

• Implementation: Pure Python using standard library (smtplib, poplib, imaplib)

  • No external tool dependencies
  • Cross-platform (Windows, Linux, macOS)
  • Works on any Python 3.10+ environment

Output Format:

• Valid users discovered via SMTP enumeration
• Working credentials (username, password, protocol, server, port)
• Email service type and version
• Protocol availability (which protocols respond on target)
• Comprehensive failure logging for debugging

Run

# Dry-run (check tools, detect DCs, preview commands)
python -m adpentest --target 10.0.0.1 --mode dry-run --scope-confirmed

# Active scan with auto DC detection
python -m adpentest --target corp.local --mode active --scope-confirmed

# With custom timeout, no auto-install
python -m adpentest --target 192.168.1.10 --mode active --scope-confirmed --timeout 600 --no-auto-install

# With custom DNS servers (fallback to public DNS on failure)
python -m adpentest --target 192.168.1.10 --mode active --scope-confirmed --dns-server 1.1.1.1,1.0.0.1

# With custom DNS timeout (in seconds)
python -m adpentest --target 192.168.1.10 --mode active --scope-confirmed --dns-timeout 5.0

DNS Configuration

The framework supports flexible DNS resolver configuration with automatic fallback:

CLI Arguments

• --dns-server <servers> — Comma-separated list of custom DNS servers (e.g., 8.8.8.8,8.8.4.4)
• --dns-timeout <seconds> — DNS query timeout in seconds (default: 3.0)

Environment Variables

• DNS_SERVERS — Comma-separated DNS servers (e.g., export DNS_SERVERS=8.8.8.8,8.8.4.4)
• DNS_TIMEOUT — DNS query timeout in seconds (e.g., export DNS_TIMEOUT=5.0)

Priority Order

1. CLI Arguments (--dns-server, --dns-timeout) — Highest priority
2. Environment Variables (DNS_SERVERS, DNS_TIMEOUT)
3. System Default DNS — Automatically detected from system configuration
4. Public DNS Fallback — Automatically uses 8.8.8.8, 8.8.4.4, 1.1.1.1, 1.0.0.1 if others fail

Examples

# Use custom DNS servers from CLI
python -m adpentest --target corp.local --mode active --scope-confirmed --dns-server 192.168.1.1,8.8.8.8

# Use environment variables for DNS
export DNS_SERVERS=192.168.1.1,1.1.1.1
export DNS_TIMEOUT=5.0
python -m adpentest --target corp.local --mode active --scope-confirmed

# Combine CLI with custom timeout
python -m adpentest --target corp.local --mode active --scope-confirmed --dns-server 8.8.8.8 --dns-timeout 10.0

Resolver Behavior

• System DNS is queried first by default
• Automatic fallback to public DNS (Cloudflare, Google) on timeout or resolution failure
• Detailed logging shows which resolver is used and why (system, environment, CLI, or fallback)
• All DNS functions (SRV records, PTR lookups, forward resolution) use centralized configuration

Requirements

• Python 3.10+
• dnspython, ldap3, httpx

This project does not authorize testing by itself. Operators must supply an explicitly authorized scope.