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SMTP Penetration Testing

Automate SMTP server security testing for open relays and weak authentication.

Updated Apr 6, 2026
Search Tags:#penetration testing#network security#SMTP#security assessment#email security
One-click install
npx skills add https://github.com/gerald-ica/dev-tool-configs --skill smtp-penetration-testing-gerald-ica
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: SMTP Penetration Testing
Source: https://github.com/gerald-ica/dev-tool-configs/tree/main/gemini/skills/smtp-penetration-testing
Command: npx skills add https://github.com/gerald-ica/dev-tool-configs --skill smtp-penetration-testing-gerald-ica

SYSTEM DOCUMENTATION & REQUIREMENTS

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

What problem does it solve?

This Skill automates SMTP security testing to help identify and assess potential vulnerabilities in SMTP servers, ensuring the integrity and security of email communications.

Core Features & Use Cases

  • Security Assessment: Comprehensive assessment of SMTP server security, including open relays, user enumeration, weak authentication, and misconfiguration.
  • User Enumeration: Discover valid email addresses for further security analysis.
  • Open Relay Testing: Identify if the server allows unauthorized relay of emails.
  • Brute Force Authentication: Test for weak SMTP credentials.
  • TLS/SSL Security Testing: Evaluate encryption configuration.
  • SPF, DKIM, DMARC Analysis: Check email authentication records for security.

Quick Start

Perform an SMTP security test on a target server using the SMTP Penetration Testing skill.

Frequently Asked Questions about SMTP Penetration Testing

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

FAQPage Schema
How do I automate SMTP security testing to check for open relays and user enumeration?▼

SMTP security testing identifies server vulnerabilities including open relays, user enumeration, weak authentication, and misconfiguration. It applies to IT security and compliance workflows to ensure email communication integrity through comprehensive automated scanning and testing.

How do I test for weak SMTP credentials and brute force authentication?▼

Test for weak SMTP credentials by executing brute force authentication attacks against the target server. This process identifies weak login credentials and misconfigurations, ensuring robust authentication mechanisms protect against unauthorized access.

Do I need to install nmap and metasploit to perform SMTP penetration testing?▼

Yes, comprehensive SMTP penetration testing requires nmap, netcat, hydra, smtp-user-enum, and metasploit. These dependencies provide the necessary network scanning, brute force, and exploitation frameworks to identify and assess server vulnerabilities.

Can I check SPF, DKIM, and DMARC records during an SMTP security assessment?▼

Yes, an SMTP security assessment includes SPF, DKIM, and DMARC analysis to check email authentication records. It also evaluates TLS/SSL encryption configuration to identify potential security misconfigurations and ensure robust email security.

What is the best way to discover valid email addresses through SMTP user enumeration?▼

Discover valid email addresses through automated SMTP user enumeration using smtp-user-enum. This technique identifies existing user accounts on the target server for further security analysis and vulnerability assessment.

Why does my SMTP server allow unauthorized email relay and how can I test for it?▼

SMTP servers allow unauthorized relay due to misconfigurations. Test for open relay vulnerabilities by automating security scans to identify if the server permits unauthorized email routing, ensuring proper configuration and preventing abuse.

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