re: Mail Server problem / query

From: Mel Drews (flyingdervish_at_hotmail.com)
Date: 04/14/05

  • Next message: Joachim Schipper: "Re: Netcat through Squid HTTP Proxy"
    To: m_davison@talk21.com
    Date: Thu, 14 Apr 2005 11:03:10 -0700
    
    

    When I discovered a client who had a server allowing this kind of forwarding
    I flagged it as a vulnerability. Our staff CISSP said not to worry about
    it, that most mail servers do this. I tested our own (Postfix) and found
    that it was doing the same. Found a way in postfix to change this. It does
    require having 2 mail servers. One is your filtering system that performs
    virus and spam checks; the other is your internal system. This is best
    practice anyway. Every network should either have 2 mail servers or a
    hosted mail service. We'll call the external facing system that does the
    scanning the "relay server". Make a change to postfix's main.cf file
    specifying a check_sender_access table. The table you create will list all
    of your internal users' legitimate email addresses. Hash tables are fairly
    easy to deal with but may not be suitable for larger networks. There are a
    variety of different kinds and I am not an expert on this topic. But at
    least this may point you in a direction to investigate. One solution I have
    seen involved pulling a list of internal email addresses from the internal
    mail server via ldap query and parsing the list into a hash table with a
    perl script. With this configuration, the internal mail server will still
    accept mail from internal users, but the relay server will only accept mail
    from external users.

    For more info, see the section re: check_sender_access in the postfix
    configuration documentation at postfix.org
    http://www.postfix.org/postconf.5.html

    Further information: With MS Exchange, there does not appear to be any way
    to shut off this behavior. With Exchange 2003 and Outlook 2003 combination,
    there's at least a half-assed effort to alert users to the problem. With
    older versions, Exchange automatically resolves the purported sender address
    to the internal Global Address List user display name if the purported
    sender is internal. With the new combination, if the message was sent from
    an external IP, the name will not be resolved. So the user sees the mail
    from: address as the raw smtp address instead. Of course, how many users
    will pick up on that?

    Hope this helps

    m_davison@talk21.com wrote:
    ---------------------------------------------------------
    Hi all, I hope you can help with this. I have been
    testing a server for open-relay and found that I could
    connect from an external machine and send mails using
    a MAIL FROM (the local domain) and a RCPT TO (the
    local domain) - now this may seem fine as internal
    users will need to send mail to other internal users
    but my query is whether there are mail servers which
    can be configured to recognise that the connection was
    an external address and therefore that the MAIL FROM
    address was invalid. eg I can send a mail from the CEO
    of the company to his own secretary asking her to copy
    his hotmail address on all future mails and to the
    secretary, this mail seems perfectly valid yet me
    (prospective attacker) outside the comapany may now
    receive loads of sensitive mails (assuming the
    secretary is the type who doesn't like to query things
    and ask questions) - thanks in advance.

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