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Corporation in the Middle Lee Brotherston @synackpse #BSidesTO Edition

Corporation In The Middle - BSidesTO Edition

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Page 1: Corporation In The Middle - BSidesTO Edition

Corporation in the Middle

Lee Brotherston!@synackpse

#BSidesTO

Edition

Page 2: Corporation In The Middle - BSidesTO Edition

MITM vs Everything Else

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Detection

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o_O

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How, what, why, when?

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Capture all the Packets

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PCAP Toolstcpdump wireshark

tshark !

mergecap tcpsplice tcptrace captcp

pcapdiff tcpflow snort

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SYN

ServerClient

SYN/ACK

ACK

HTTP Request

HTTP Response (Header & Data)

More Data……

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SYN

ServerClient

SYN/ACK

ACK

RST/PSH/ACK

HTTP Response

HTTP Request

?

??

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HTTP/1.1 200 OK!Content-Type: text/html; charset=ISO-8859-1!Content-Script-Type: text/javascript!Connection: close!Cache-Control: no-store, no-cache, must-revalidate, max-age=0!Expires: -1!Pragma: no-cache!!

<html><head><noscript><meta http-equiv="refresh" content="0;URL=http://64.71.251.10/noscript.pl?policy=72&category=ByteCap-075&"></noscript><title></title><script type="text/javascript">var version=2; var webServer="http://64.71.251.10";</script><script type="text/javascript" src="http://64.71.251.10/ByteCap-075-EO-English/index.js"></script></head><noscript><frameset><frame src="http://64.71.251.10/noscript.pl?policy=72&category=ByteCap-075&"></frameset></noscript><body style="margin:0;"><script type="text/javascript">Bulletin("policy=72&category=ByteCap-075&");</script></body></html>

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Packet Headers

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TCPDUMPip[6] = 0 and tcp[14:2] = 1

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Wire/TSharktcp.window_size_value eq 1

and ip.flags.df == 0

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Snortalert tcp $EXTERNAL_NET any -> $HOME_NET any (msg:"INJECTION

suspected TCP injection"; flow:stateless; window:1; fragbits:!D; sid:31337)

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But wait, there’s more….

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SYN

ServerClient

SYN/ACK

ACK

RST/PSH/ACK

HTTP Response

HTTP Request

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SYN

ServerClient

SYN/ACK

ACK

HTTP Request

HTTP Response (Header & Data)

Data

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HTTP/1.1 200 OK!Content-Type: text/html; charset=ISO-8859-1!Content-Script-Type: text/HTML!Connection: close

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Profiling Target Acquisition

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Retention Timerewrite ^(.*)$ /index.php;!

!

!

!

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OoB Indexingrewrite ^(.*)$ /index.php;!

+!/etc/hosts!

+!.htaccess

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Document Format!

<html>!<head>!<title>Oh Hai</title>!</head>

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Document Format<!doctype html>!<html>!<head>!<title>Oh Hai</title>!</head>

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– PIPEDA, 4.9 Principle 9 — Individual Access !

“Upon request, an individual shall be informed of the existence, use,

and disclosure of his or her personal information and shall be given access to that information.”

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Mapping the Network

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Traceroute (8 bits of goodness)

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ttl=1

ttl expiry

ttl=2

ttl expiry

ttl=1

reply

ttl=2 ttl=1ttl=3

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2 7.40.72.1! 3 209.148.241.61! 4 66.185.81.221! 5 69.63.251.242! 6 69.63.249.26! 7 *!!

2 7.40.72.1! 3 209.148.241.61! 4 *! 5 *! 6 69.63.249.26! 7 *!

tcptraceroute

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Intercept Portscanningfor i in `jot 65535 1`!do !tcptraceroute -f4 -m5 host $i!done >> $i.log

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2 7.11.164.41! 3 66.185.90.37! 4 209.148.224.205! 5 209.148.224.242!!

!

!

6 4.31.208.129

2 7.11.164.41! 3 66.185.90.37! 4 209.148.224.214! 5 209.148.224.209! 6 209.148.228.218! 7 209.148.228.217! 8 209.148.224.254! 9 4.31.208.129

tcptraceroute redux

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Intercept Portscanning Reduxnmap -sS —-ttl 64 host

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Which Interface?

My Server

DestinationMe

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Scapysendp(Ether(dst="be:ef:11:11:11:11", src="31:33:7a:aa:aa:aa")/IP(src="11.11.11.11", dst="55.55.55.55",ttl=(1,30), options=IPOption('\x07'))/TCP(sport=3125, dport=80, flags="S"), iface="en1")

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So, that network…

Internal Management LAN

extWebServer = "http://64.71.255.194";!intWebServer = “http://172.19.11.72";

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SYN

ServerClient

SYN/ACK

ACK

RST/PSH/ACK

TTL = 1

TTL = 2

TTL = 3

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What?

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HTTP/1.1 200 OK!Date: Thu, 22 May 2014 14:29:09 GMT!Server: PerfTech!Last-Modified: Thu, 17 Apr 2014 14:42:01 GMT!Accept-Ranges: bytes!Content-Length: 2387!Connection: close!Cache-Control: no-store, no-cache, must-revalidate, max-age=0!Expires: -1!Pragma: no-cache!Content-Type: application/x-javascript

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Hints in Scripts// Copyright 2005-2011 PerfTech, Inc., All Rights Reserved.!!

!

!

displayUrl = "http://www.perftech.com/console/original.html";!

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Why So Bothered?

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Why Metadata Matters• They know you rang a phone sex service at 2:24 am and spoke

for 18 minutes. But they don't know what you talked about.!!

• They know you called the suicide prevention hotline from the Golden Gate Bridge. But the topic of the call remains a secret.!!

• They know you spoke with an HIV testing service, then your doctor, then your health insurance company in the same hour. But they don't know what was discussed.

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GET / HTTP/1.1!Host: squarelemon.com!User-Agent: Mozilla/5.0 (X11; Ubuntu; Linux i686; rv:25.0) Gecko/20100101 Firefox/25.0!Accept: text/html,application/xhtml+xml,application/xml;q=0.9,*/*;q=0.8!Accept-Language: en-US,en;q=0.5!Accept-Encoding: gzip, deflate!Cookie: _pk_ses.4.9b83=*!Connection: keep-alive!If-Modified-Since: Fri, 18 Oct 2013 14:45:41 GMT!Cache-Control: max-age=0

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What could possibly go

wrong?Photo Attribution: Tom - @tdawks

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I learnt Stuff!

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–Johnny Appleseed

“Type a quote here.”

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Internet provider subscriber communications system US 8793386 B2

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Internet advertising method and system using Web page US 8005717 B2

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– Hanlon’s Brotherston’s Razor

“Never attribute to malice that which is adequately explained by stupidity Enhancing Shareholder

Value.”

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Thank you!Lee Brotherston!

@synackpse!