RE: ESTMP Exploits & Security

From: Dante Mercurio (Dante_at_webcti.com)
Date: 03/17/04

  • Next message: Bill Geschwind: "RE: SPYWARE detection"
    Date: Wed, 17 Mar 2004 13:34:42 -0500
    To: "JTH" <jth@visi.com>, <security-basics@securityfocus.com>
    
    

    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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  • Next message: Bill Geschwind: "RE: SPYWARE detection"

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