SMTP Penetration Testing

Automate SMTP security testing for mail server vulnerabilities.

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

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This Skill helps security teams automate comprehensive SMTP security testing to identify vulnerabilities such as open relays, user enumeration, weak authentication, and misconfigurations in mail servers.

Core Features & Use Cases

  • Automated discovery & banner grabbing: Identify server details and supported features.
  • Enumeration & relay testing: Detect valid users and potential open relays.
  • Brute-force & TLS checks: Assess credential strength and encrypted communication.
  • Use Case: Example workflow for assessing a corporate mail server in a controlled, authorized engagement.

Quick Start

Run an authorized assessment against target-smtp.example.com using the included workflow and toolchain.

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 for open relays and user enumeration?

Automate SMTP security testing by running an authorized assessment workflow that performs banner grabbing, user enumeration, open relay testing, and brute-force authentication validation against target mail servers. This identifies server vulnerabilities and misconfigurations using tools like nmap and hydra.

What is SMTP user enumeration and how does it expose mail server vulnerabilities?

SMTP user enumeration identifies valid email accounts on a mail server by analyzing server responses to specific commands. It exposes vulnerabilities by revealing valid usernames, which attackers can target for brute-force authentication attacks or phishing campaigns.

Can I test DKIM, SPF, and DMARC configurations during an SMTP penetration test?

Yes, you can test DKIM, SPF, and DMARC configurations during an SMTP penetration test. The assessment includes analyzing these email authentication protocols to detect misconfigurations that could allow email spoofing or unauthorized message delivery on target infrastructure.

Do I need written authorization to run an SMTP brute-force assessment on a corporate mail server?

Yes, you need written authorization to run an SMTP brute-force assessment on a corporate mail server. This security testing requires explicit permission to access the target SMTP infrastructure, ensuring the evaluation of credential strength remains legal and compliant.

What tools are required to perform TLS testing and open relay checks on SMTP servers?

Required tools for TLS testing and open relay checks include nmap, smtp-user-enum, hydra, and metasploit, along with wordlists for brute-force discovery. These tools validate encrypted communication and detect potential relay vulnerabilities on target servers.

What is the best way to assess weak authentication and TLS misconfigurations in cloud mail systems?

The best way to assess weak authentication and TLS misconfigurations in cloud mail systems is running an end-to-end automated security assessment. This applies authorized brute-force authentication checks and TLS/SSL validation to identify credential strength and encrypted communication vulnerabilities.