SMTP Penetration Testing

Assess SMTP servers for open relays, user enumeration, and weak authentication.

Updated Jan 8, 2026
One-click install
npx skills add https://github.com/AndyAnh174/BanThuoc-SEO --skill smtp-penetration-testing-andyanh174
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: SMTP Penetration Testing
Source: https://github.com/AndyAnh174/BanThuoc-SEO/tree/main/.agent/skills/smtp-penetration-testing
Command: npx skills add https://github.com/AndyAnh174/BanThuoc-SEO --skill smtp-penetration-testing-andyanh174

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill requires nmap, netcat, hydra, smtp-user-enum, metasploit-framework, and includes scripts (resource) and references (resource) components.

What problem does it solve?

This Skill helps identify and mitigate security vulnerabilities in SMTP servers, preventing unauthorized access, email spoofing, and data breaches.

Core Features & Use Cases

  • Vulnerability Assessment: Detects open relays, user enumeration flaws, and weak authentication.
  • Security Hardening: Provides actionable recommendations to secure mail server configurations.
  • Use Case: A security analyst needs to assess the security posture of a company's mail server before a major product launch. This Skill will systematically test for common SMTP vulnerabilities.

Quick Start

Perform a comprehensive SMTP penetration test against the mail server at 'mail.example.com'.

Frequently Asked Questions about SMTP Penetration Testing

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I test my SMTP server for open relay and user enumeration vulnerabilities?

To test an SMTP server for open relay and user enumeration vulnerabilities, this Skill analyzes SMTP banners and enumerates users via VRFY, EXPN, and RCPT commands to identify configuration flaws.

What is SMTP user enumeration and how does it expose email server weaknesses?

SMTP user enumeration is a technique that exposes email server weaknesses by querying commands like VRFY and EXPN to verify valid usernames, which can lead to unauthorized access and data breaches.

How to perform a brute-force attack on SMTP credentials using Hydra and Metasploit?

To perform a brute-force attack on SMTP credentials, you can use tools like Hydra and Metasploit-framework to systematically test weak authentication mechanisms and identify vulnerable accounts on the target mail server.

Does this SMTP penetration testing approach require Nmap and Netcat to check TLS configurations?

Yes, this SMTP penetration testing approach requires Nmap and Netcat alongside smtp-user-enum to comprehensively check TLS and SSL configurations and detect security misconfigurations on the target server.

Can I assess the security posture of a mail server before a product launch using this method?

Yes, you can assess the security posture of a mail server before a product launch by conducting a systematic security assessment to detect open relays, weak authentication, and user enumeration flaws.

What are the limitations of SMTP penetration testing for preventing email spoofing?

Limitations of SMTP penetration testing include its focus on identifying vulnerabilities like open relays and weak authentication rather than directly implementing fixes, requiring manual hardening to fully prevent email spoofing.