SMTP user enumeration for fun and profit

Sometimes it is desirable to enumerate all (or as much as possible) email recipients at given domain. This can be done by establishing SMTP connection to corresponding mail server that can be found via DNS MX record and getting the server to verify your guesses for email usernames or addresses.

There are three major approaches to do this:

  • Using VRFY request that is meant to verify if there is user with corresponding mailbox on the server. Server would respond with status code 250 if address is valid, 251 if it’s not, 252 if it cannot be determined.
  • Using EXPN request that is meant to give a list of subscribers to a mailing list. Some email servers consider every user to be in a list of single member, others do not. On success, server would respond with status code 250 and a list of subscribers in implementation-specific format.
  • Using RCPT request that is designed to add one more recipient to the email being sent out. On success the SMTP server would respond with status code 250 or 251. Note that the SMTP protocol disallows more than 100 recipients being sent the same email message and that for some servers the limit may be lower.

We will be primarily focusing on recipients that use Gmail/GSuite/Google Workspaces for their email service. Let us use some Unix tools to manually check-and-verify some email addresses on domain peopledatalabs.com.

As a first step, we need to find out a hostname of mail server for this domain. We use dig(1) for this:

$ dig -t MX peopledatalabs.com

; <<>> DiG 9.10.6 <<>> -t MX peopledatalabs.com
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 44234
;; flags: qr rd ra ad; QUERY: 1, ANSWER: 5, AUTHORITY: 0, ADDITIONAL: 1

;; OPT PSEUDOSECTION:
; EDNS: version: 0, flags:; udp: 512
;; QUESTION SECTION:
;peopledatalabs.com.		IN	MX

;; ANSWER SECTION:
peopledatalabs.com.	3600	IN	MX	1 aspmx.l.google.com.
peopledatalabs.com.	3600	IN	MX	10 alt3.aspmx.l.google.com.
peopledatalabs.com.	3600	IN	MX	10 alt4.aspmx.l.google.com.
peopledatalabs.com.	3600	IN	MX	5 alt1.aspmx.l.google.com.
peopledatalabs.com.	3600	IN	MX	5 alt2.aspmx.l.google.com.

;; Query time: 66 msec
;; SERVER: 8.8.8.8#53(8.8.8.8)
;; WHEN: Sat Apr 02 13:50:38 EEST 2022
;; MSG SIZE  rcvd: 162

Now we can use NetCat to establish SMTP connection to SMTP server:

$ nc aspmx.l.google.com 25
220 mx.google.com ESMTP i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

Let us start a SMTP transaction by sending HELO and MAIL FROM messages:

HELO test.example.org
250 mx.google.com at your service
MAIL FROM: <a@example.org>
250 2.1.0 OK i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

So far, so good. We’re getting valid responses to our requests. Let us try sending VRFY request to check an email address we know to be valid:

VRFY <support@peopledatalabs.com>

We get a response that is inconclusive and fails to give us an answer whether this address is valid:

252 2.1.5 Send some mail, I'll try my best i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

We get the same response if we try to verify a made up email address:

VRFY <fakefakefake@peopledatalabs.com>
252 2.1.5 Send some mail, I'll try my best i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

Thus we conclude that VRFY method is not applicable to enumerate addresses on Google-hosted email domains.

But what about EXPN method? Let us try it:

EXPN <support@peopledatalabs.com>
502 5.5.1 Unimplemented command. i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

This seems to be explicitly unsupported. Only option left is trying RCPT method, which succeeds:

RCPT TO: <support@peopledatalabs.com>
250 2.1.5 OK i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp
RCPT TO: <fakefakefake@peopledatalabs.com>
550-5.1.1 The email account that you tried to reach does not exist. Please try
550-5.1.1 double-checking the recipient's email address for typos or
550-5.1.1 unnecessary spaces. Learn more at
550 5.1.1  https://support.google.com/mail/?p=NoSuchUser i23-20020a2ea237000000b002495e9ab777si3826740ljm.545 - gsmtp

By using RCPT verb, we can conclusively verify if email address at Google-managed email domain is valid or not.

Now let’s try doing the same step in Python REPL with dnspython and smtplib modules:

>>> import dns.resolver
>>> answers = dns.resolver.resolve('peopledatalabs.com', 'MX')
>>> answers
<dns.resolver.Answer object at 0x109101910>
>>> answers[0]
<DNS IN MX rdata: 1 aspmx.l.google.com.>
>>> str(answers[0].exchange)
'aspmx.l.google.com.'
>>> smtp_hostname = str(answers[0].exchange)
>>> conn = smtplib.SMTP(smtp_hostname)
>>> conn.helo('test.example.org')
(250, b'mx.google.com at your service')
>>> conn.mail('FROM: <a@example.org>')
(250, b'2.1.0 OK u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp')
>>> conn.vrfy('support@peopledatalabs.com')
(252, b"2.1.5 Send some mail, I'll try my best u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp")
>>> conn.vrfy('fakefakefake@peopledatalabs.com')
(252, b"2.1.5 Send some mail, I'll try my best u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp")
>>> conn.expn('support@peopledatalabs.com')
(502, b'5.5.1 Unimplemented command. u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp')
>>> conn.rcpt('support@peopledatalabs.com')
(250, b'2.1.5 OK u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp')
>>> conn.rcpt('fakefakefake@peopledatalabs.com')
(550, b"5.1.1 The email account that you tried to reach does not exist. Please try\n5.1.1 double-checking the recipient's email address for typos or\n5.1.1 unnecessary spaces. Learn more at\n5.1.1  https://support.google.com/mail/?p=NoSuchUser u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp")
>>> conn.quit()
(221, b'2.0.0 closing connection u30-20020ac25bde000000b00449fff281b7si4479810lfn.313 - gsmtp')

A simple Python script that takes a wordlist and domain via CLI arguments to enumerate SMTP users at given domain would look like the following:

#!/usr/bin/python3

import smtplib
import sys

import dns.resolver  # requires dnspython


def make_smtp_conn(smtp_hostname):
    conn = smtplib.SMTP(smtp_hostname)

    conn.helo("gmail.com")
    conn.mail("FROM: <a@gmail.com>")

    return conn


def main():
    if len(sys.argv) != 3:
        print("Usage:")
        print("{} <wordlist> <domain>".format(sys.argv[0]))
        return

    domain = sys.argv[-1]

    answers = dns.resolver.resolve(domain, "MX")

    if len(answers) == 0:
        print("Error: no MX records found for {}".format(domain))
        return -1

    in_f = open(sys.argv[1], "r")

    smtp_hostname = str(answers[0].exchange)

    conn = make_smtp_conn(smtp_hostname)

    n = 0

    for line in in_f:
        line = line.strip()

        email_addr = line + "@" + domain

        status, _ = conn.rcpt(email_addr)
        if status == 250:
            print(email_addr)

        n += 1
        if n % 99 == 0:
            conn.quit()
            conn = make_smtp_conn(smtp_hostname)

    conn.quit()


if __name__ == "__main__":
    main()

Let us create a very basic wordlist with some entries from RFC 2142 and other common words found in email addresses:

abuse
noc
security
postmaster
hostmaster
usenet
news
webmaster
www
uucp
ftp
support
info
sales

Running the above script with this wordlist on peopledatalabs.com domain prints the following valid email addresses to standard output:

$ python3 smtp_enum.py basic_wordlist.txt peopledatalabs.com
abuse@peopledatalabs.com
security@peopledatalabs.com
postmaster@peopledatalabs.com
support@peopledatalabs.com
sales@peopledatalabs.com

If we wish to be more serious about enumerating a significant portion of email addresses at any given domain we need to take a proper care to acquire or generate a proper wordlist. Quality of the wordlist largely makes or breaks the success of SMTP user enumeration. If you know that email addresses at certain company follow a certain pattern and are based on names and surnames of employees (e.g. john.smith@example.org) you would want to generate your wordlist based on this pattern. You may also want to look into public wordlists (e.g. from danielmiessler/SecLists repo) to use them as starting point for creating your own.

Furthermore, email providers do have some countermeasures against SMTP enumeration. For example, I found that Google starts reporting all email addresses as non-existent if the above script launches bunch of checks repeatedly from single IP address in a short timeframe - probably due to triggerring some rate limits. This should be addressable by introducing delays into code (SMTP connection may need to be re-established) or by spreading the traffic across multiple connections tunneled through SOCKS proxies. I would not recommend doing this sort of shenanigans at non-trivial scale from home IP adddress. Some email providers also reject the SMTP transaction if source domain address is weird (e.g. example.org). This can be fixed by simply using a domain with a popular email service in HELO and MAIL messages in the beginning.

What are the possible applications of SMTP user enumeration? Growth hackers can use it to source email addresses for cold outreach or ad targeting. OSINT investigators can use it to cover more ground in their research. Penetration testers and social engineers can leverage email list gathered via SMTP enumeration for further attacks. When it comes to bug bounties, SMTP username enumeration is generally not considered to be a vulnerability by itself as RCPT method cannot truly be prevented due to RCPT request being an integral part of a regular email sending flow, but one could argue that it’s a security problem if it is too easy to perform. For example, someone received $300 bounty for reporting that VRFY method is possible on a certain server, besides other problems with SMTP (see HackerOne report #138315).

Trickster Dev

Code level discussion of web scraping, gray hat automation, growth hacking and bounty hunting


By rl1987, 2022-04-02