SMTP Enumeration

SMTP

• port: 25/tcp

Connect

$ nc -nv $IP 25
Ncat: Version 7.92 ( https://nmap.org/ncat )
Ncat: Connected to 10.11.1.217:25.
220 hotline.localdomain ESMTP Postfix
VRFY noone^M
550 5.1.1 <noone>: Recipient address rejected: User unknown in local recipient table

CRLF

SMTP servers often expect CRLF line endings, so use ^V^M (Ctrl-V Ctrl-M) to enter carriage returns in the terminal; note that ^V does not get echoed.

VRFY Username Enumeration

Related:userenum See SecLists for username wordlists.

#!/usr/bin/env python
import socket
import sys
 
if len(sys.argv) != 3:
    print("Usage: {} <ip> <usernames-file>".format(sys.argv[0]))
    sys.exit(1)
 
with open(sys.argv[2]) as f:
    s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
    connect = s.connect((sys.argv[1],25))
    banner = s.recv(1024)
    for username in f:
        username = username.rstrip('\n')
        s.send(('VRFY ' + username + '\r\n').encode('ascii'))
        result = s.recv(1024)
        if b'rejected' not in result:
            print(username)
    s.close()
 

EXPN User and Mailing List Enumeration

Verify whether jacob is a mailbox / jacob is a valid user:

EXPN jacob
250 [email protected]

List all members of the users mailing list / check whether users mailing list exists:

EXPN users
[email protected]
[email protected]
[email protected]
250 [email protected]

The - indicates that it’s not the last line.