Individual skill

performing-email-security-testing

Offensive email security assessment covering SMTP open relay, SPF/DKIM/DMARC bypass, email header injection, and email-based attack vectors during authorized penetration tests.

internal/tools/skills/data/web-application-security/performing-email-security-testing/SKILL.md

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Nov 9, 2026

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Nov 9, 2026
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Apache-2.0

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# Performing Email Security Testing

## When to Use

- During Phase 15 (Email Security Testing) of the methodology
- When the target has email infrastructure (MX records, webmail, contact forms)
- When testing for email spoofing or phishing susceptibility
- When the application handles email input (forms, notifications, password resets)
- When testing email-based authentication flows (magic links, OTP via email)

### How to CONFIRM a Hit (avoid false negatives)

- **Positive signal**: a spoofed message actually **passes/bypasses SPF, DKIM, and DMARC and is delivered** to the inbox; an open relay actually **delivers** a third-party message; or CRLF header injection actually **adds a recipient/header** in the received mail.
- Confirm by delivery to your controlled test inbox (agentmail) and by reading the **received `Authentication-Results` headers** (spf=pass/none, dmarc=pass/none) — a DNS record showing `~all`/`p=none` is suggestive but delivery is the proof.
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