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Special Forums Cybersecurity how to hide the IP in the email header? Post 7217 by Neo on Thursday 20th of September 2001 11:34:15 PM
Old 09-21-2001
It is not a just a matter of spoofing the sending IP. SMTP is based on TCP which is connection oriented. The exploit most commonly used is when one or more intermediate SMTP relays are used to relay the mail combined with dirty tricks in the SMTP protocol exchange.

I agree with PxT that there are not too many defensible scenarios to send anonymous email or mask the originating machine. The potential for abuse may far outweigh the benefit for good.
 

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auth-relaytest(1)					      General Commands Manual						 auth-relaytest(1)

NAME
auth-relaytest - attempt to use authenticated SMTP to relay to a DSBL-compliant host SYNOPSIS
auth-relaytest [-tv] ntlm <ip address[:port]> auth-relaytest [-tv] (cram-md5|login) <username> <password> <ip address[:port]> DESCRIPTION
auth-relaytest attempts to connect to the specified <ip address> on the specified port (default is port 25) and tries to use the supplied authentication data to relay mail through the host. auth-relaytest uses the sender_user, sender_domain, target_user, target_domain, and auth-message parameters from dsbl.conf(5) by default. If the auth-message parameter is not present, the message parameter is used instead. In the first mode of operation shown, auth-relaytest attempts to authenticate using anonymous NTLM authentication. A well-known bug in cer- tain Microsoft SMTP server implementations (described at http://www.microsoft.com/technet/security/bulletin/MS02-011.asp) will allow relay- ing for any client that authenticates in this way. In the second form of operation, auth-relaytest attempts to authenticate using either the cram-md5 or login variant of SMTP AUTH, using the supplied username and password. OPTIONS
-t Test mode. Instead of using the target_domain parameter from dsbl.conf(5), the test_target_domain parameter is used instead. This is useful for sending a test message to yourself, perhaps to check that the server is actually relaying the messages. -v Verbose mode. Details of the SMTP transaction are written to standard output. AUTHORS
Paul Howarth <paul@city-fan.org> Ian Gulliver <ian@penguinhosting.net> SEE ALSO
dsbl.conf(5), spamtrap(1), relaytest(1) 2004-01-06 auth-relaytest(1)
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