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Armitage and Metasploit Penetration Testing Lab Raphael Mudge [email protected] Twitter: @armitagehacker

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Page 1: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Armitage and Metasploit Penetration Testing Lab

Raphael [email protected]: @armitagehacker

Page 2: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Penetration Testing

Armitage and Metasploit Penetration Testing Lab

Page 3: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Overview

Personal Introduction Penetration Testing Process Course Overview

Page 4: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Introduction – R. Mudge

Previous Experiences Penetration Tester Regional CCDC Red Team x 5 USAF Security Researcher Armitage for Metasploit

Other Experiences WordPress Grammar Checker Programming Language

Page 5: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Penetration Testing

What? Test security by doing what bad guys might do

Page 6: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Penetration Testing

Why? Motivate desire to make changes to improve security

Page 7: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Penetration Testing

How? Demonstrate risk

Page 8: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Types of Penetration Tests Open Source Research Network Social Engineering Wireless Web Applications Mobile

Page 9: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Penetration Testing Process Information Gathering Reconnaissance Access Post-Exploitation

Page 10: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Network Attack Process

Page 11: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Motivation

Page 12: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Motivation

Page 13: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Course overview

1.Penetration Testing2.Metasploit 3.Getting Access4.Post Exploitation5.Maneuver

Page 14: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Goals

• Install Metasploit• Get Access to Hosts• Post-exploitation

Page 15: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Learning Check

Who is Raphael Mudge?

Why Penetration Test?What are we doing today?

Page 16: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Metasploit

Armitage and Metasploit Penetration Testing Lab

Page 17: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Overview

What is Metasploit? Modules Metasploit Console Armitage

Page 18: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

What is Metasploit?

Page 19: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

What is Metasploit?

Metasploit Linux Modules

Programs msfconsole

/bin/bash RPC Daemon sshd

Page 20: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Modules

Page 21: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Modules

Page 22: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Modules and Magic the Gathering

© 1995-2011 Wizards of the Coast

Page 23: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Module Organization

Page 24: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Metasploit Command Sets

Metasploit Console Manage Database Manage Sessions Configure and Launch Modules

Meterpreter Post-exploitation activities

Page 25: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Console Cheat Sheet

use module - start configuring module

show options - show configurable options

set varname value - set optionexploit - launch

exploit modulerun - launch

non-exploit

sessions –i n - interact with a session

help command - get help for a command

Page 26: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

msfconsole

Open ended Works in many places One task / host at a time

Page 27: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

What is Armitage? A GUI for Metasploit Goal: Avoid this…

Page 28: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Armitage

Page 29: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Armitage Sightings…

Page 30: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Console Demo

Page 31: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Learning Check

What is a session?What is a payload?What do exploits do?

Page 32: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Getting Access

Armitage and Metasploit Penetration Testing Lab

Page 33: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Overview

Remote Exploits Exploit-free Attack Client-side Exploits

Page 34: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Network Attack Process

Page 35: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Remote Attack

1. NMap Scan2. Analyze Scan Data3. Choose an Exploit4. Select a Payload5. Launch Exploit!

Page 36: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Which exploit do I use? Answer: These.

Name Where

ms08_067_netapi Windows XP/2003 era

ms09_050_smb2_negot..

Windows Vista SP1/SP2

ms03_026_dcom Windows 2000

Page 37: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Why did my exploit fail?

Firewall Non-vulnerable software Service is hung The universe is taunting you Non-reliable exploit Bad day Mis-configured exploit Could not establish session

Page 38: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Exploit-free Attack

1. Choose a payload2. Generate executable3. Set up a multi/handler

Page 39: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

PayloadsName Note

windows/meterpreter/reverse_tcp Connects to one port

windows/meterpreter/reverse_tcp_allports

Tries every ports in sequence

windows/meterpreter/reverse_https Speaks HTTPS (!!!!)

java/meterpreter/reverse_tcp Any platform with Java

linux/x86//shell_reverse_tcp

osx/x86/shell_reverse_tcp

Page 40: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Client-side Attack

1. Fingerprint sample of victims2. Choose an Exploit3. Launch Expoit 4. Spam victims (or wait for them)!

Page 41: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Which exploit do I use? Answer: These.Name Where

java_signed_applet Social engineering; any where Java applets run

ms11_003_ie_css_import

Internet Explorer 7/8 (requires .NET)

ie_createobject Internet Explorer 6

Page 42: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Learning Check

Which module listens for a connection from a payload?

Which exploit works against Windows XP SP2, port 445?

Page 43: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Post-Exploitation

Armitage and Metasploit Penetration Testing Lab

Page 44: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Overview

Command Shell Privilege Escalation Spying on the User File Management Process Management Post Modules and Loot

Page 45: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Network Attack Process

Page 46: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Demo Demo Demo

Page 47: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Learning Check

Which Meterpreter command takes a screenshot?

Which Meterpreter command is most useful to you?

Page 48: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Maneuver

Armitage and Metasploit Penetration Testing Lab

Page 49: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Overview

Pivoting Scanning Attacking

Page 50: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Network Attack Process

Page 51: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Demo Demo Demo

Page 52: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Learning Check

Which module gives a session on a Windows host using credentials or hashes?

Which scan should you do before setting up a pivot?

Page 53: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Network Attack Process

Page 54: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Resources

Armitage and Metasploit Penetration Testing Lab

Page 55: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Free Metasploit Course

http://www.offensive-security.com/metasploit-unleashed

Page 56: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Metasploit Homepage

http://www.metasploit.com

Page 57: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Armitage Homepage

http://www.fastandeasyhacking.com

Page 58: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

BackTrack Linux

http://www.backtrack-linux.org/

Page 59: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Pen Test & Vuln Analysis Course @ NYU

http://pentest.cryptocity.net

Page 60: Armitage and Metasploit Penetration Testing Lab Raphael Mudge rsmudge@gmail.com rsmudge@gmail.com Twitter: @armitagehacker

Armitage and Metasploit Penetration Testing Lab

Raphael [email protected]: @armitagehacker