home | O'Reilly's CD bookshelfs | FreeBSD | Linux | Cisco | Cisco Exam  


sendmailSearch this book
Previous: 22.2 The Environment Chapter 22
Next: 22.4 The Configuration File

22.3 SMTP Probes

Although SMTP probes can be legitimate uses of the network, they can also pose potential risks. They are sometimes used to see whether a bug remains unfixed. Sometimes they are used to try to gather user login names or to feed a program unexpected input in such a way that it breaks and gives away root privilege.

22.3.1 SMTP debug

An "unfixed bug" probe can use the SMTP debug and showq commands. The SMTP debug command allows the local sendmail to be placed into debugging mode (as with the -d command-line switch; see Section 37.1, "The Syntax of -d" ) from any other machine anywhere on the network. The SMTP showq command allows outsiders to view the contents of the mail queue.

If SMTPDEBUG (see Section 18.8.42, SMTPDEBUG ) is defined when sendmail is compiled, the SMTP debug and showq commands are allowed to work; otherwise, they are disabled. SMTPDEBUG should be defined only when modifying the sendmail code and testing a new version. It should never be defined in an official release of sendmail . To see whether it has been defined at your site, run the following command:


telnet localhost 25

Trying ...
Connected to localhost.
Escape character is '^]'.
220 localhost sendmail 8.8.4 ready at Fri, 13 Dec 1996 06:36:12 -0800


500 Command unrecognized


221 localhost.us.edu closing connection
Connection closed by foreign host.

When connected, enter the command debug . If you get the answer 500 Command unrecognized , you know that SMTPDEBUG is not enabled. If, on the other hand, you get the answer 200 Debug set , SMTPDEBUG is defined on your system, and you should immediately take steps to correct the situation. Either contact your vendor and request a new version of sendmail , or get the sendmail source and compile it with SMTPDEBUG undefined.

When SMTPDEBUG is undefined and an outsider connects to the local machine and attempts to execute the debug or showq commands, sendmail will syslog (3) a message like the following:

Jul 22 07:09:00 here.domain sendmail[192]: "debug" command from there.domain 


This message shows the name of the machine that attempts the probe, or ( there.domain ), and the IP address of that machine. Note that this message is logged only if the LogLevel ( L ) option (see Section 34.8.33, LogLevel (L) ) is nonzero.

22.3.2 SMTP vrfy and expn

You may be dismayed to learn that the login names of ordinary users can be used to break into a system. It is not, for example, all that unusual for a user to select a password that is simply a copy of his or her login name, first name, last name, or some combination of initials. A risk of attack can arise from outsiders guessing login names. Any that they find can be used to try to break in, and the SMTP vrfy gives an attacker the means to discover login names.

The SMTP vrfy command causes sendmail to verify that it will accept an address for delivery. If a user's login name is given, the full name and login name are printed:

vrfy george

250 George Washington <george@wash.dc.gov>

Here, the 250 SMTP reply code (see RFC821) means a successful verification. [7] If the user is unknown, however, sendmail says so:

[7] See the F=q flag ( Section 30.8.36, F=q ) for a way and reason to change this SMTP reply code to 252.

vrfy foo

550 foo... User unknown

The SMTP expn command is similar to the vrfy command, except that in the case of a mailing list, it will show all the members of that list. The SMTP expn command causes sendmail to expand (show all the recipients) of an address. To illustrate the risk, consider that many sites have aliases that include all or a large segment of users. Such aliases often have easily guessed names, such as all , everyone , or staff . A probe of all , for example, might produce something like the following:

expn all

250-George Washington <george@wash.dc.gov>
250-Thomas Jefferson <tj@wash.dc.gov>
250-Ben Franklin <ben@here.us.edu>
250-Betsy Ross <msflag@ora.com>
250 John Q. Public <jqp@aol.com>

With well-designed passwords these full and login names can safely be given to the world at large. But if one user (say jqp ) has a poorly designed password (such as jqpublic ), your site's security can easily be compromised. [8] Note that not all uses of vrfy or expn represent probes. Some MUAs, [9] for example, routinely vrfy each recipient before sending a message.

[8] The fingerd (8) utility can also reveal login IDs.

[9] The GNU fingerd (8) daemon also uses vrfy to provide mailbox information.

SMTP vrfy and expn commands are individually logged in a form like one of the following:

Sep 22 11:40:43 yourhost sendmail[pid]: other.host: vrfy all
Sep 22 11:40:43 yourhost sendmail[pid]: []: vrfy all
Sep 22 11:40:43 yourhost sendmail[pid]: other.host: expn all
Sep 22 11:40:43 yourhost sendmail[pid]: []: expn all

This shows that someone from the outside ( other.host in the first and third examples) attempted to probe for usernames in the mailing list named all . In the second and last examples the probing hostname could not be found, so the IP address is printed instead (in the square brackets). Note that this form of logging is enabled only if the LogLevel ( L ) option (see Section 34.8.33 ) is greater than 5.

Pre-V8 versions of sendmail do not report SMTP vrfy or expn attempts at all. Some versions of sendmail (such as the HP_UX version) appear to verify but really only echo the address stated.

V8 sendmail allows vrfy and expn services to be selectively accepted or rejected on the basis of the setting of the PrivacyOptions ( p ) option (see Section 34.8.47, PrivacyOptions (p) ). For best security we recommend this setting:

O PrivacyOptions=goaway

Previous: 22.2 The Environment sendmail Next: 22.4 The Configuration File
22.2 The Environment Book Index 22.4 The Configuration File