Penetration Testing mailing list archives

RE: EXAMPLE: Why OOO is *BAD* [WAS: Re: OOO FLAME]


From: "Alexandru Bradescu-Popa" <alexbp () alexbp ro>
Date: Mon, 15 Sep 2008 17:53:39 +0300

Interesting security procedures they have. Help-desk with access on
/etc/shadows. No written request for high sensitive files. They'll pass with
flying colors any security audit.

______________________________________________________________
Frank, whatever it is, just write it down and put it on my desk where I
can't find it.
Henry Blake - M*A*S*H

-----Original Message-----
From: listbounce () securityfocus com [mailto:listbounce () securityfocus com] On
Behalf Of Tim March
Sent: 15 septembrie 2008 08:39
To: pen-test () securityfocus com
Subject: Re: EXAMPLE: Why OOO is *BAD* [WAS: Re: OOO FLAME]


A secretary with access to the '/etc/shadow' file... and the means to 
pull it off of the machine and in to her email client... *giggles to self*



T.

Jon Kibler wrote:
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Hash: SHA1

Erin Carroll wrote:
List,

Let's take Ray's tangent and run with it. What (if any) ways are OOO
messages useful from a pen-test perspective? How would you use the
knowledge
that someone is away/on vacation in a pen-test? Would you alter your
techniques or target those accounts specifically in the hopes that brute
force or other account specific techniques might have a window to go
unnoticed?

I'm just trying to get a conversational ball rolling here. I know where I
would modify my tactics but I'm curious to see what members say. I know
that
one area many companies are historically weak is in logging of security
events. Or rather, in having someone actually pay attention to all those
alerts.



Okay, since I started this, you're on!

Real world example...

I was teaching a pen-test bootcamp several years ago. One of the
students (who I will call 'Joe') pooh-poohed the whole OOO message
issue. He even indicated that he used them all the time, that they were
harmless, and they saved him from getting calls to his cell phone at
roaming rates when he was out of town. (This was back in the days before
nationwide calling plans.)

I then sent Joe a test email message at his work email address. I got
back an OOO message saying that he would be out of the office for two
weeks of training and would only have very limited email at night. His
signature line showed that he was the dep-CSO for his organization.

I then displayed the email for the whole class to discuss. Next, I
proposed that we demonstrate why OOO messages are an issue.

What I proposed was to social engineer the help desk into providing
sensitive information. Rather arrogantly, he said, "Sure, why not? Those
guys are well trained and would never fall for anything you could
contrive." We then got permission (in writing) from the CIO, the CSO,
and the organization's legal department to do the social engineering
attack.

Next, I wrote up a script for a secretary (who I will call 'Sue') at
that ed center to use to call the organization's help desk. It basically
went as follows:

   Sue: "Hi, I'm Sue with abc training company. One of your employees,
Joe, is taking a security course from us and he forgot that he was
supposed to bring the /etc/shadow file from the user file store server.
He needs it to use in class to test password cracking. He asked that you
please gzip it and email it to him."

   Help Desk: "Okay, but I will have to check with his manager first."

   Sue: "Oh, Joe said that if you needed to verify that he was taking a
course from us, just send him an email and the OOO reply it will have
everything you need to know."

   Help Desk: "Alright, give me a minute. (Pause) Okay, I guess this has
everything I need. But, it says that he has limited email access; does
he want it sent to his office email address?"

(This just shows that help desks are trained to be helpful!!! Despite
continual security awareness training, the possibility that this might
be social engineering attack never even occurred to this guy!)

   Sue: "No, I was just about to tell you that he asked to have you it
send to his Hotmail address, which is: joe.... () hotmail com."

   Help Desk: "Okay, no problem, he should have it in about 5 minutes."

Needless to say, we had just created the hotmail account a few minutes
prior to the phone call.

In just a couple of minutes, we owned the shadow file from the file
server where all user accounts have their data stored. In other words,
we now pwned the passwords for every one of his users.

After that b-slap with a clue-by-4, Joe started singing a different tune.

Jon K.
- --
Jon R. Kibler
Chief Technical Officer
Advanced Systems Engineering Technology, Inc.
Charleston, SC  USA
o: 843-849-8214
c: 843-224-2494
s: 843-564-4224
http://www.linkedin.com/in/jonrkibler

My PGP Fingerprint is:
BAA2 1F2C 5543 5D25 4636 A392 515C 5045 CF39 4253


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-- 
Tim March
P: +61 (0)406 577 276
E: march.tim () gmail com

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Securing Web Applications
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