Penetration Testing mailing list archives

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


From: "Hill, Pete" <Pete.Hill () sit-up tv>
Date: Tue, 16 Sep 2008 10:23:03 +0100

Sorry Tim, but I think you have missed the point a little as have a
number of others.

The secretary was not the one with access to the file.  The secretary
was the secretary at the education centre that staged the attack.  All
she did was request the file from "Joes" companies helpdesk.  

-----Original Message-----
From: listbounce () securityfocus com [mailto:listbounce () securityfocus com]
On Behalf Of Tim March
Sent: 15 September 2008 23:52
To: pen-test () securityfocus com
Subject: Re: EXAMPLE: Why OOO is *BAD* [WAS: Re: OOO FLAME]


I didn't miss the point -- just found the story questionable.


T.

Pablo Cardoso wrote:
Tim, I'm guessing you missed the point. The secretary called the 
tech-support of Joe's company, she was the one requesting the 
/etc/shadow file from the server :P!!!

Excellent scenario, Jon, thanks for sharing!

Regards,
Pablo Cardoso

On Mon, Sep 15, 2008 at 2:39 AM, Tim March <march.tim () gmail com>
wrote:
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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