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RE: ESTMP Exploits & Security
From: "Dante Mercurio" <Dante () webcti com>
Date: Wed, 17 Mar 2004 13:34:42 -0500

I seem to remember a firewall or gateway product that distinguished
telnet attempts to an SMTP service by the fact that a manual telnet
session sends each character in a separate packet, and a true mail
connection does not.

I don't remember much detail, but may be a good place to start.

M. Dante Mercurio
dante () webcti com
Consulting Group Manager
Continental Technologies, Inc
www.webcti.com

-----Original Message-----
From: JTH [mailto:jth () visi com] 
Sent: Wednesday, March 17, 2004 12:12 PM
To: security-basics () securityfocus com
Subject: RE: ESTMP Exploits & Security


-----Original Message-----
From: Jeff McLaughlin [mailto:JMclaughlin () springsgov com]
Sent: Wednesday, March 10, 2004 9:50 AM
To: security-basics () securityfocus com
Subject: RE: ESTMP Exploits & Security

I'm looking for info on exploits and security of ESMTP when you telnet

into port 25.  I understand how to telnet in and send email via the 
command line
but trying to understand the security implications of being able to do
this.
I am currently looking at this on Exchange 5.5.

Does ESMTP from the command line need to be "accessible" for the apps 
to work or enabled to troubleshoot?

Are their DDOS attacks or hacks against ESMTP?

Is there a best practice to secure ESMTP

I've been able find info about ESMTP (commands) but not much info on 
the potential security risks.

Also, exploits with telnetting to 110 i.e., POP3 ??

Warning, this rambles, and I haven't had much coffee. ;)

I'd like some information on this as well. From what I understand, 25
must be open and accept incoming mail without any sort of
authentication. The risk of being an open relay is mitigated by only
accepting mail for the local domain. However, no checking is ever done
(that I have seen) to determine if the sender of a message is _also_
from the local domain.

This is nice from a penetration testing aspect, because I can get an
email from my client, write an email that looks like he or she wrote it,
send it through the _client's_ SMTP server, and if I asked employees to
do something, more often than not, they will. For example, I've sent a
security "survey" out that requested the user go to a website and login
to fill out the survey. From what I've seen, users will use their
network credentials in this situation. This (from what I've read) is how
the Beagle viruses (and probably others) have propagated.

This has been the biggest hole I have identified, but it doesn't seem to
be considered a hole. And I haven't seen any way to prevent this from
happening, either. 

I've heard mention of a postfix SMTP gateway, but that's not a very good
solution for many of my clients. 

An alternative has been to try to find a configuration change to make.
Is there a way to filter incoming email based on the FROM: header? If
so, I could deny incoming mail with an internal FROM: address. Another
solution I've heard of is third-party software that behaves similarly.

I've also seen mention of enabling/requiring SMTP AUTH, effectively
breaking the mail server, as most servers do not use this.

Another solution is to utilize public-key cryptography, but for many of
my clients this is an administrative and educational nightmare. In this
vein, perhaps an integrated public-key crypto email server solution is
better, where the keys, signing & verification are performed on the
server. This may keep internal mail internal.

So what do you all think. Have you seen solutions, are you even aware of
this [apparent] design flaw in SMTP?


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any course! All of our class sizes are guaranteed to be 10 students or less
to facilitate one-on-one interaction with one of our expert instructors.
Attend a course taught by an expert instructor with years of in-the-field
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of an Ethical Hacker to better assess the security of your organization.
Visit us at:
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