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rahmatullahboss
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SMTP Penetration Testing

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

Updated Jan 4, 2026
Search Tags:#security#penetration testing#encryption#smtp#relays#email servers
One-click install
npx skills add https://github.com/rahmatullahboss/multi-store-saas --skill smtp-penetration-testing-rahmatullahboss
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: SMTP Penetration Testing
Source: https://github.com/rahmatullahboss/multi-store-saas/tree/main/.agent/skills/SMTP%20Penetration%20Testing
Command: npx skills add https://github.com/rahmatullahboss/multi-store-saas --skill smtp-penetration-testing-rahmatullahboss

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) and references (resource) components.

What problem does it solve?

This Skill addresses the need for security assessment of SMTP servers by identifying vulnerabilities such as open relays, user enumeration, and weak authentication.

Core Features & Use Cases

  • Vulnerability Detection: Find open relays and insecure configurations that could be exploited for spam or unauthorized access.
  • User Enumeration: Discover valid email addresses using SMTP commands and tools.
  • Security Hardening: Provide recommendations to enhance SMTP server security, including TLS enforcement and SPF/DKIM/DMARC deployment.
  • Use Case: An organization wants to verify if their mail server is vulnerable to relay abuse and to detect valid users for further security audits.

Quick Start

Use the SMTP penetration testing skill to scan your mail server for open relays, enumerate users, and check TLS support by running targeted nmap and command-line tools.

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 relays?▼

Test SMTP servers for open relays by executing targeted nmap and command-line scripts to identify insecure configurations that allow unauthorized mail routing. This process detects vulnerabilities that could be exploited for spam relay abuse.

What is SMTP user enumeration and how does it work?▼

SMTP user enumeration discovers valid email addresses on a mail server by analyzing responses to specific SMTP commands. This technique helps map valid accounts for further security audits and infrastructure assessments.

How can I check if my mail server supports TLS encryption?▼

Check mail server TLS encryption support by evaluating the server's encryption configurations using command-line testing tools. This verifies whether secure transport is enforced and identifies missing encryption protocols.

Can I test SMTP authentication weaknesses using nmap?▼

Yes, you can test for weak authentication on SMTP servers by running targeted nmap scripts and command-line utilities. This identifies weak login mechanisms and credentials susceptible to brute force or unauthorized access.

What security hardening recommendations apply after an SMTP penetration test?▼

After an SMTP penetration test, security hardening recommendations include enforcing TLS, deploying SPF, DKIM, and DMARC records, and closing open relays. These actions secure email infrastructure against abuse and spoofing.

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