SMTP Penetration Testing

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

Updated Jan 12, 2026
One-click install
npx skills add https://github.com/giosuetedeschi-spec/bobu-website --skill smtp-penetration-testing-giosuetedeschi-spec
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: SMTP Penetration Testing
Source: https://github.com/giosuetedeschi-spec/bobu-website/tree/main/.claude/skills/smtp-penetration-testing
Command: npx skills add https://github.com/giosuetedeschi-spec/bobu-website --skill smtp-penetration-testing-giosuetedeschi-spec

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This skill addresses the critical need for identifying vulnerabilities in mail server configurations, such as open relays, weak authentication, and information disclosure, which are frequently exploited by attackers.

Core Features & Use Cases

  • Vulnerability Assessment: Detects open relays, weak authentication, and missing security headers.
  • User Enumeration: Identifies valid email addresses through VRFY, EXPN, and RCPT command testing.
  • Security Hardening: Provides actionable recommendations to secure SMTP infrastructure against unauthorized access and spoofing.

Quick Start

Use the SMTP Penetration Testing skill to perform a comprehensive security assessment on the mail server at 192.168.1.100.

Frequently Asked Questions about SMTP Penetration Testing

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

FAQPage Schema
How do I check an SMTP server for open relay vulnerabilities?

To check for open relay vulnerabilities on an SMTP server, conduct a penetration test using Nmap and Netcat to attempt unauthorized mail routing. This identifies misconfigurations that allow external message spoofing.

How does SMTP user enumeration work during a network security audit?

SMTP user enumeration identifies valid email addresses by analyzing server responses to VRFY, EXPN, and RCPT commands. This technique exposes valid accounts during a network security audit for further targeted attacks.

Do I need Hydra and Metasploit to test weak authentication on mail servers?

Yes, you need Hydra and Metasploit to test weak authentication on mail servers. These tools execute protocol-specific testing and command injection analysis required to evaluate SMTP server security configurations.

Can I use SMTP penetration testing for mail server hardening?

Yes, you can use SMTP penetration testing for mail server hardening. The assessment detects missing security headers and weak authentication, providing actionable recommendations to secure infrastructure against unauthorized access.

What is the best way to detect information disclosure in SMTP configurations?

The best way to detect information disclosure in SMTP configurations is conducting a comprehensive security assessment using Nmap. This protocol-specific testing identifies exposed user data and server vulnerabilities during audits.