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Advanced Tutorial: Man in the Middle

Attack Using SSL Strip Our Definitive
Guide

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PMP Practice Exams

We got a lot of great feedback from our first Man in the Middle Video so we decided to double-down
and give you guys some really juicy MitM demos and analysis. Our Ethical Hacking students have been
really excited about this one during classes, so I wanted to share some of the good stuff here.
This one shows how to use SSLStrip with a MitM attack. We first give a demo of the attack and in the
next two videos you can really gain an understanding and the practical knowledge of how it functions.
If you want to follow along, everything is really within BackTrack4, but the individual

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DEMO OF THE MitM ATTACK WITH SSLSTRIP:

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Microsoft
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About the Author

Keatron Evans

Keatron, one of the two lead

authors of "Chained Exploits:
Advanced Hacking Attacks From

EXPLANATION OF HOW IT WORKS PART 1:

Start to Finish", is a Senior

Instructor and Training Services
Director at InfoSec Institute.

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Director at InfoSec Institute.

Keatron is regularly engaged in
training and consulting for
members of the United States
intelligence community, military,
and federal law enforcement
agencies. Keatron specializes in
penetration testing

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CONTINUED EXPLANATION OF HOW IT WORKS PART 2:

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Want to learn more?? The InfoSec Institute Ethical Hacking course goes indepth into the techniques used by malicious, black hat hackers with
attention getting lectures and hands-on lab exercises. While these hacking
skills can be used for malicious purposes, this class teaches you how to use
the same hacking techniques to perform a white-hat, ethical hack, on your
organization. You leave with the ability to quantitatively assess and measure
threats to information assets; and discover where your organization is most
vulnerable to black hat hackers. Some features of this course include:

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By Keatron Evans | November 19th, 2010 | Hacking | 27 Comments

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About the Author: Keatron Evans

Keatron, one of the two lead authors of "Chained Exploits: Advanced Hacking Attacks
From Start to Finish", is a Senior Instructor and Training Services Director at InfoSec
Institute. Keatron is regularly engaged in training and consulting for members of the
United States intelligence community, military, and federal law enforcement agencies.
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Keatron specializes in penetration testing and digital forensics. In addition to training, Keatron serves as
Senior Security Researcher and Principle of Blink Digital Security which performs penetration tests and
forensics for government and corporations.

27 Comments

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crazyred

a year ago

Hello keatron, i want to study your class for Backtrack 5 . can i study from internet?

Vaskez

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2 years ago

Ah, I just saw one of your other comments - maybe the certificate ISN'T automatically accepted by the client, the
method relies on the client just clicking through OK and not worrying about warning messages about the certificate?
correct?

Vaskez

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2 years ago

Hi Keatron - or anyone that can answer. Very nice videos, but I don't quite understand one of the steps in the
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EXPLANATION OF HOW IT WORKS PART 1: video. I understand certificate chaining, but why would the client
accept a certificate for e.g. google.com.infosecinstitute.co... when it wants to get to
issues a fake valid certificate, why would it get accepted when the name doesn't exactly match? Even if the
browser's set up to match & accept *.google.com - it'd still have to END in google.com
top-level domain, no? what am I missing, why is the certificate accepted from the MITM? thanks a lot

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Peter Andrews

2 years ago

Is there a workaround if we don't have a trusted certificate to issue leaves from?

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Richard Arnold

3 years ago

Keatron
Excellent video. I have been trying to conduct this on my own but I have no luck finding arp spoof on the net. The one
that I found was a rar file. I am not sure on how to load that successfully. Can you advs.
Richard Arnold

George

Reply Share

3 years ago

Hey this is awesome man. Keep up the good work. Wonderfull

keatron

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3 years ago

Ananya, make sure you can actually ping the target ip's. Usually when you can't arp them it's because you can't
communicate with them.
Kyubi, you can comment out the rule you added. You can also remove it by entering the exact command again, but
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add the -D option. You can also do iptables -L -n -v --line to see a list of rules. Then once you find the line you added,
enter iptables -D (number of the line which is your rules).

Steven

Reply Share

3 years ago

To the people having trouble: The most obvious reason of why is because this video should have been trashed and
redone, there are so many mistakes, breeze-overs of important aspects, and not to mention the authentication
attempts he makes in the video aren't even using SSL!! just HTTP, you can even see this in his ettercap output near
the end.
I will make a video that clearly documents how to edit your etter.conf file (btw, ananya it should be located at
/etc/etter.conf if it isn't there I would re-configure ettercap via dpkg) how to add (and REMOVE) needed changes to
IPTABLES, as well as show you how to write these steps into a script using variables for your target, instead of
having 9 term-emus open.

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Ananya Sethi

3 years ago

performed the steps exactly as mentioned. But the response to

#arpspoof -t 192.168.196.129 192.168.196.2
is
arpspoof: couldn't arp for host 192.168.196.129
also i m using ubuntu and there is no file etter.conf in path mentioned so cudn't modify that too.

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kyubi

3 years ago

@Amnesiac : you have to check on the file "ssstrip.log".. try typing "tail -f sslstrip.log" in the terminal

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kyubi

3 years ago

hello sir.. i was thinking.. how could you then bring back the original settings of the IPtables after you have stop doing
all the MITM attack thing.. will it auto set it self to default after you stop doing the MITM attack.. thanks please
response..

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Amnesiac

3 years ago

hi, i tried everything in this post, even tried different posts but i cant get the sslstrip program to capture anything, it
runs fine, i have set my iptables and ports, arpspoofs working and i also use ettercap, but when i get to the point of
actually getting the packets i get nothing, i just get this:
sslstrip 0.9 by Moxie Marlinspike running
and it doesnt capture anything. Any ideas??? Im using backtrack 5.

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Keatron Evans

3 years ago

@Ronnie. Check out our online courseware offerings. Just go to our main website www dot infosecinstitute dot c0m
then select the online courses link.

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Keatron Evans

3 years ago

@DJ. I've been experimenting since I was 13 or 14. Been doing this professionally about 14 years.

DJ

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3 years ago

I think this is fantastic. I've been getting Cisco certifications and am relatively new to the network security realm.
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wanted to thankyou for spending the time to compile this site; and wanted to ask you how long you have been
researching and experimenting with pen testing to become so good.

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ronnie short

4 years ago

great video so you do classes what about online ?

Reply Share

Zacharius

4 years ago

i might have to take a trip to Chi for a class...im at ITT and im learning this aswell...very interesting and great video!

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Joel Carlson

4 years ago

I don't think this information is completely correct. SSLStrip does not certificate chain by signing a valid certificate
from a leaf certificate. It just redirects a https to an http thus removing the need for certificates, at least for the client
to mitm session. Everything else appears correct. The automatic leaf signing use to be done by sslsniff, however,
that doesn't work any more since nowadays most browsers check the basicconstraints which verify the entire chain.
Correct me if I am wrong. The guy who created sslstrip has a great explaination in his blackhat 2009 whitepaper.

Keatron

Reply Share

4 years ago

The way it works is it picks out HTTP traffic from port 80 and then packet forwards onto a different port (10,000 in this
case).
SSLStrip is at the same time listening on that port and removes the SSL connection before passing it back to the
user.
Ettercap then picks out the username & password.
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Yes, there would be an additional SSL warning that says this certificate cannot be validated or something of that
nature. Whether or not the victim gets that message depends on the browser they're using, how the browser is
configured, etc. Using this method takes that possibility out of the equation completely.

Kateter

Reply Share

4 years ago

Why is the client redirected to HTTP instead of HTTPS? Will there be additional SSL warning pop-ups if the client
keeps the SSL-session to the SSL Strip box, that decrypts it with the certificate that was presented and then
establishes a new SSL-session to yahoo.com instead of redirecting the client to a HTTP-page? It would still be
possible to capture the content and the client keeps the HTTPS url?

Keatron

Reply Share

4 years ago

@Pieface and Gary. Working on something for it guys. Thanks.

Pieface

Reply Share

4 years ago

"So for the next video, can you show us how to detect that there is a man in the middle, or a security technique
where a man can not get into the middle?"
+1
id like to see counter measure video if possible.
thx

Keatron

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4 years ago

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@Gary. No problem.

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Gary Fisher

4 years ago

So for the next video, can you show us how to detect that there is a man in the middle, or a security technique where
a man can not get into the middle?

Matt

Reply Share

4 years ago

Just came across your site/videos and I like them a lot; keep them up!!

Reply Share

Keatron Evans

4 years ago

@Aaron. Yes we do classes in Chicago all the time after all we're based in the area! What type of class are you
looking for? You can start by looking at our course catalog, then come back here and discuss.
http://www.infosecinstitute.co...

Reply Share

Aaron Klutz

4 years ago

This is freaking awesome! I'd heard about being able to do this, but this is the first time I've ever seen it proven.
Keatron I'm in Chicago. Do you do classes here?

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1 comment 25 days ago

tipkin I really like

two guys discussing

Robin Hii please helpD:\tel>telnet

192.168.0.140Connecting To

Overview of Automated Malware Analysis in the

Cloud
1 comment 11 days ago

Does Blackhat Accurately Depict Cyberwarfare?

1 comment 14 days ago

Marc Great analysis

.asm "Therefore we can be fairly certain that this

of the security elements

current sample is malicious, because valid

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