RE: Email Pen-testing

From: Reava, Jeffrey (jeffrey.reava_at_pfizer.com)
Date: 03/22/04

  • Next message: Meidinger Chris: "RE: how to alert company of security hole"
    To: Blake <netspan@hotmail.com>, pen-test@securityfocus.com
    Date: Sun, 21 Mar 2004 23:32:41 -0500
    
    

    "Doing a pen-test...A friend of mine suggested [sending] a backdoor
    trojan attachment via an email. If they clicked on it, the backdoor
    performs [miscellaneous evil things] ... I think this type of testing is
    becoming more relevant nowadays, especially with whats out there..."

    >> Absolutely more relevant. Why would an attacker do any more work then
    they have to in order to get what they want? Every organization with
    assets worth protecting should fully expect that they're going to get
    Googled, their staff and operations profiled, and their end users
    attacked directly. It happened to Valve software last September, rather
    spectacularly: http://mac.ign.com/articles/453/453038p1.html?fromint=1

    "I spoke with a previous customer of mine about the idea. He said he
    would be very upset if he was not told prior to that type of test as
    part of normal pen-testing...Generally speaking, my code of ethics
    doesn't allow me to social engineer. I don't like lying and misleading
    people. Also people tend to hate you after they've been punk'd."

    >> With the IE and Outlook holes, it may not even be necessary to
    socially engineer anyone. You'd just need a small number of "high value"
    targets to send messages to.

    What's your ideas on the email pen-tesing?

    >> Even if it puts the success of your efforts at risk, I think you need
    to get permission to go this road. You can still mine for information
    without lying, but walking that line will take some serious effort.
    Check out http://www.csoonline.com/read/050103/snooping.html

    If you make people feel stupid, they'll definitely hate you. But if you
    approach it within some reasonable bounds and they give you small pieces
    that individually appear innocent and yet make your technical attack
    much more focused and effective, your client will benefit by recognizing
    the problem because the gap in their policies and practices will be
    painfully evident.

    Jeff

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