SMTP Penetration Testing

Purpose

Conduct comprehensive security assessments of SMTP (Simple Mail Transfer Protocol) servers to identify vulnerabilities including open relays, user enumeration, weak authentication, and misconfiguration. This skill covers banner grabbing, user enumeration techniques, relay testing, brute force attacks, and security hardening recommendations.

Prerequisites

🧠 Knowledge Modules (Fractal Skills)

1. Required Tools

2. Required Knowledge

3. Required Access

4. Phase 1: SMTP Architecture Understanding

5. Phase 2: SMTP Service Discovery

6. Phase 3: Banner Grabbing

7. Phase 4: SMTP Command Enumeration

8. Phase 5: User Enumeration

9. Phase 6: Open Relay Testing

10. Phase 7: Brute Force Authentication

11. Phase 8: SMTP Command Injection

12. Phase 9: TLS/SSL Security Testing

13. Phase 10: SPF, DKIM, DMARC Analysis

14. Essential SMTP Commands

15. SMTP Response Codes

16. Enumeration Tool Commands

17. Common Vulnerabilities

18. Legal Requirements

19. Technical Limitations

20. Ethical Boundaries

21. Example 1: Complete SMTP Assessment

22. Example 2: User Enumeration Attack

23. Example 3: Open Relay Exploitation

24. For Administrators