Email penetration testing part – #1

Greetings,

Hope everyone is safe and Secure

In this series of Blogs, we will be learning how to do Email Penetration Testing. Methodology to carry out in Pentesting Email

We will be doing lots of Things in this Series of Blogs. They are

1. Introduction to Email Security
2. Commonly Used Email Service Protocols
3. Prerequisites for Email Penetration Testing
4. Email Pentesting Steps
5. SMTP Fingerprinting
6. Directory Harvesting Attacks
7. NTLM Overflows Attack
8. Crack Email Passwords
9. Checking against Phishing and Spamming Attack
10. Perform Email bombing
11. Check against CLSID Extension and VBS attachment Vulnerability
12. Performing Fragmented Message vulnerability Test
13. Recommendations.

So Let’s Dive in

Today we are going to see first Four Steps of our Objective only.

INTRODUCTION TO EMAIL SECURITY

These days People tend to store their Private Information, Business Information in Emails as Repositories.

Everyone is using Internet and Email These days, that’s what gives Confidence to hackers as well. Attackers can find ways easily to compromise the security of Email Systems and access the user’s Sensitive Information.

COMMONLY USED EMAIL SERVICE PROTOCOLS

PREREQUISITES FOR EMAIL PENETRATION TESTING

1. Should Possess the Knowledge of Email Terminology and Concepts.
2. Official documents giving you Permission to test the Email Security of the Client Organization
3. Clearly read Rules of Engagement (ROE) before proceeding.
4. Armory of Tools
5. Incase if it is a white Box testing
   1. Common email Policy of Organization & how it is maintained
   2. Official Mail Server IP address, domain Name, etc.
   3. A test email ID and address to perform penetration testing.
      

STEPS FOR EMAIL PENETRATION TESTING

STEP1 : Perform SMTP Service Fingerprinting.
STEP2 : Perform directory Harvest Attacks
STEP3: Enumerate enabled SMTP subsystems and features
STEP4: Perform SMTP Password Bruteforcing
STEP5: Perform NTLM overflows attack through SMTP authentication
STEP6: Test for SMTP open relay
STEP7: SMTP User Enumeration
STEP8: Perform POP3 password brute-forcing
STEP9: Perform IMAP brute-forcing.
STEP10: Test for IMAP process manipulation attack
STEP11: Check for known vulnerabilities in mail servers and hosts
STEP12: Check the patch status of mail server and host systems
STEP13: Try to crack email passwords
STEP14:Check whether anti-Phishing tools are enabled
STEP15:Check whether anti-spamming tools are enabled
STEP16:Try to perform email bombing
STEP17:Perform CLSID extension vulnerability test
STEP18:Perform VBS attachment Vulnerability Test
STEP19:Perform double file extension vulnerability test
STEP20:Perform long file name vulnerability test
STEP21:Perform malformed file extension vulnerability test
STEP22: Perform access exploit vulnerability test
STEP23:Perform fragmented message vulnerability test
STEP24:Perform long subject attachment checking test
STEP25:Perform no file attachment vulnerability test

We will be performing all the steps to Email penetration Testing in the Upcoming Blogs

Stay tuned with our Pentesting Series of Blogs.

Learn more, secure enough.

Thanks, Bye!

Author:
Sam Nivethan V J
Security Analyst & Infosec Train