SMTP Penetration Testing

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

1|Updated Dec 15, 2025
One-click install
npx skills add https://github.com/jokken79/YuKyuDATA-app1.0v --skill smtp-penetration-testing-jokken79
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: SMTP Penetration Testing
Source: https://github.com/jokken79/YuKyuDATA-app1.0v/tree/main/.agent/skills/smtp-penetration-testing
Command: npx skills add https://github.com/jokken79/YuKyuDATA-app1.0v --skill smtp-penetration-testing-jokken79

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

This skill helps security professionals rapidly identify SMTP server vulnerabilities, including open relays, user enumeration capabilities, weak authentication, and TLS misconfigurations, reducing exposure and hardening posture.

Core Features & Use Cases

  • Banner grabbing and version disclosure to assess exposure.
  • User enumeration and open-relay testing to verify access controls and abuse potential.
  • Brute-force authentication testing, TLS/SSL checks, and SPF/DKIM/DMARC analysis for defense-hardening.
  • Remediation guidance and best practices for securing SMTP infrastructure.

Quick Start

Begin an initial SMTP security assessment by discovering services on the target server, capturing the banner, and testing for open relay.

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 for an open relay on an SMTP server?

To test for an open relay on an SMTP server, you simulate sending an email from an external address to an external domain through the target server. This SMTP security assessment identifies misconfigurations that allow unauthorized mail routing and spam abuse.

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

Yes, you can analyze SPF, DKIM, and DMARC configurations during an SMTP penetration test. This evaluates email spoofing protections and domain authentication policies to verify defense-hardening against phishing and fraudulent mail delivery.

What is the best way to enumerate SMTP users on a corporate mail server?

The best way to enumerate SMTP users is by probing the server with commands like VRFY, EXPN, or RCPT TO. This security assessment verifies access controls by identifying valid email addresses and existing accounts on the target infrastructure.

How does TLS misconfiguration testing work for SMTP security assessments?

TLS misconfiguration testing works by initiating STARTTLS handshakes with the mail server to evaluate certificate validity, protocol versions, and cipher suite strength. This identifies weak encryption settings that expose email traffic to interception.

Does this SMTP security assessment provide remediation guidance for weak authentication?

Yes, the SMTP security assessment provides remediation guidance and best practices after detecting weak authentication. It delivers actionable hardening recommendations to secure mail server credentials and prevent brute-force attacks.

Can I perform SMTP banner grabbing to assess mail server exposure?

Yes, you can perform SMTP banner grabbing to capture the server greeting and software version disclosure. This initial assessment step evaluates service exposure and identifies potential vulnerabilities in the target mail server implementation.