Louisiana State University

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LSU Master's Theses Graduate School

2014

Ethical Hacking Using Penetration Testing

Bharath Kumar Koopari Roopkumar
Louisiana State University and Agricultural and Mechanical College, [email protected]

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Koopari Roopkumar, Bharath Kumar, "Ethical Hacking Using Penetration Testing" (2014). LSU Master's Theses. 3238.
https://digitalcommons.lsu.edu/gradschool_theses/3238

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ETHICAL HACKING USING PENETRATION TESTING

A Thesis

Submitted to the Graduate Faculty of the

Louisiana State University and
Agricultural and Mechanical College
in partial fulfillment of the
requirements for the degree of
Master of Science

in

The Division of Electrical and Computer Engineering

by
Bharath Kumar Koopari Roopkumar
B.Tech., Jawaharlal Nehru Technological University, 2012
December 2014
 ACKNOWLEDGEMENTS

Dr. Suresh Rai has been the inspirational and wonderful person who introduced me to the

world of Networks. I sincerely thank him for the opportunity to work with him. I thank him for

immense guidance, patience and moral support towards my completion of master’s program.

My sincere thanks go to Dr. Jerry Trahan and Dr. Ramachandran Vaidyanathan for their

consent to be the committee members and for their valuable suggestions in improving this

document. I also thank Dr. Trahan for approving the proposal of purchasing new equipment for

the lab which helped me for this research.

Besides my advisor and the committee, I would like to sincerely thank Mr. Mark Hovey

for providing me financial support throughout my masters. I am thankful to him and Mr. Tim

Nguyen-Pham for helping me with computer equipment for my research.

Deepest gratitude to my parents Mr. Koopari Roop Kumar and Mrs. Koopari Padma, and

to my family for their love, and blessings. I sincerely thank my dear friend Ms. Krishna Kumari

Maddali for all the moral support and guidance.

ii
 TABLE OF CONTENTS

ACKNOWLEDGEMENTS ....................................................................................................... ii

LIST OF TABLES ..................................................................................................................... vi

LIST OF FIGURES ................................................................................................................... vii

LIST OF ABBREVIATIONS .................................................................................................... x

ABSTRACT ............................................................................................................................... xii

1. INTRODUCTION ................................................................................................................. 1
1.1 Pentester ................................................................................................................... 1
1.2 Border Gateway Protocol ......................................................................................... 2
1.3 Motivation and Thesis Layout ................................................................................. 2
1.3.1 Thesis Goal ............................................................................................... 4
1.3.2 Thesis Layout ............................................................................................ 5

2. PENETRATION TESTING – AN OVERVIEW .................................................................. 6

2.1 Basic Concepts ......................................................................................................... 6
2.1.1 Black-Box ................................................................................................. 6
2.1.2 White-Box ................................................................................................. 7
2.1.3 Gray-Box................................................................................................... 7
2.2 Systematic Approach ............................................................................................... 10
2.2.1 Planning and Preparation .......................................................................... 11
2.2.2 Information Gathering and Analysis ......................................................... 11
2.2.3 Vulnerability Detection ............................................................................. 12
2.2.4 Penetration Attempt .................................................................................. 13
2.2.5 Analysis and Reporting ............................................................................. 13
2.2.6 Cleaning Up .............................................................................................. 14
2.3 Tools and Frameworks ............................................................................................. 14
2.5 Objectives and Benefits ........................................................................................... 17

iii
 2.6 Conclusion ............................................................................................................... 17

3. BORDER GATEWAY PROTOCOL .................................................................................... 18

3.1 BGP Attributes ......................................................................................................... 19
3.1.1 Path Attributes .......................................................................................... 19
3.1.2 BGP Messages .......................................................................................... 19
3.2 Conclusion ............................................................................................................... 21

4. RELATED WORK ................................................................................................................ 22

4.1 Cisco Packet Tracer ................................................................................................. 22
4.1.1 Access Attacks .......................................................................................... 23
4.1.2 LAN Attacks ............................................................................................. 25
4.2 Graphical Numeric Simulator 3 ............................................................................... 28
4.2.1 ASA Configuration ................................................................................... 29
4.3 Cisco Configuration Professional ............................................................................ 33
4.3.1 Configure .................................................................................................. 33
4.3.2 Monitoring ................................................................................................ 34

5. IMPLEMENTATION ............................................................................................................ 35
5.1 Laboratory Setup ...................................................................................................... 35
5.1.1 Procedure .................................................................................................. 39
5.1.2 Tools and Services on PCs........................................................................ 40
5.2 Network Penetration Testing ................................................................................... 41
5.2.1 Layer 3 Assessment .................................................................................. 42
5.2.2 Layer 2 Assessment .................................................................................. 49
5.3 Application Penetration Testing .............................................................................. 57
5.3.1 Planning and Preparation .......................................................................... 57
5.3.2 Information Gathering and Analysis ......................................................... 57
5.3.3 Vulnerability Detection ............................................................................. 59
5.3.4 Penetration Attempt .................................................................................. 64
5.3.5 Analysis and Reporting ............................................................................. 71
5.3.6 Cleaning Up .............................................................................................. 71

iv
6. CONCLUSION AND FUTURE WORK .............................................................................. 73

REFERENCES .......................................................................................................................... 75

APPENDICES ........................................................................................................................... 79
Appendix 1: Laboratory Configurations ........................................................................ 79
Appendix 2: Topology and Outputs of Cisco Tools ...................................................... 80
Appendix 3: Supportive Screenshots for Pentesting ...................................................... 83
Appendix 4: Tools and Frameworks .............................................................................. 85

VITA .......................................................................................................................................... 91

v
 LIST OF TABLES

2.1 Tools ................................................................................................................................. 15

2.2 Frameworks....................................................................................................................... 16

A1.1 PC Configurations ............................................................................................................. 79

A1.2 Router Configurations ....................................................................................................... 79

A4.1 Tools Description .............................................................................................................. 85

A4.2 Frameworks Description ................................................................................................... 90

vi
 LIST OF FIGURES

1.1 A Procedure Prototype for Pen Testing ............................................................................ 2

2.1 Penetration Testing Layout ............................................................................................... 7

2.2 Types of Testing Based on the Concentration .................................................................. 9

2.3 Step by Step Pen Testing .................................................................................................. 10

3.1 Scope of BGP .................................................................................................................... 18

3.2 The Process of BGP Connection Establishment ............................................................... 20

5.1 Lab Topology for Demonstrating Application Attacks .................................................... 36

5.2 Lab Topology for Layer 3 Penetration Attacks ................................................................ 37

5.3 Lab Topology for Layer 2 Penetration Attacks ................................................................ 37

5.4 Actual Laboratory Setup ................................................................................................... 38

5.5 TCP Syn Flood Attack Script ........................................................................................... 42

5.6 Wireshark Analysis on the Victim .................................................................................... 43

5.7 Output Indicting Defense to TCP Syn Attack................................................................... 44

5.8 Python Code for LAND Attack ........................................................................................ 45

5.9 Wireshark Analysis of LAND Attack ............................................................................... 46

5.10 Filtered Packet during Defense ........................................................................................ 47

5.11 Python Code for IP Spoofing Attack ............................................................................... 48

vii
5.12 Wireshark Analysis of IP Spoofing Attack ...................................................................... 48

5.13 Nmap Scan Indicating the Active Hosts .......................................................................... 50

5.14 Python Code for Cam Flooding Attack ........................................................................... 51

5.15 Wireshark Analysis of Cam Flooding.............................................................................. 51

5.16 Cam Flooding On the Switch Console............................................................................. 52

5.17 Mac Spoofing Code ......................................................................................................... 53

5.18 Wireshark Analysis for Mac Spoofing ............................................................................ 53

5.19 Indicating Security Violation ........................................................................................... 54

5.20 STP Attack Python Code ................................................................................................. 55

5.21 Wireshark Analysis of STP Attack .................................................................................. 55

5.22 Switch Port Verification .................................................................................................. 56

5.23 Telnet on the Victim ........................................................................................................ 59

5.24 Network Scanning Via Ping Sweep ................................................................................. 60

5.25 Scanning Using Nmap ..................................................................................................... 61

5.26 Vulnerability Scan Using Nmap ...................................................................................... 63

5.27 Dradis and Nessus Results for .Xml File ......................................................................... 63

5.28 Auxiliary Scan Using Metasploit for Mssql .................................................................... 65

5.29 Password Cracking Using Hydra ..................................................................................... 66

viii
5.30 Logging Into the Target Machine .................................................................................... 66

5.31 Exploit and Payload Results ............................................................................................ 67

5.32 Windows Server 2003 Exploitation ................................................................................. 68

5.33 Results for Metasploitable Exploit................................................................................... 69

5.34 Remote Desktop Connection to the Target ...................................................................... 70

A2.1 Topology Used to Configure the ASA on GNS3 ............................................................ 80

A2.2 Communication between the LAN and DMZ ................................................................. 80

A2.3 Security Levels to the LAN, DMZ and WAN Areas in the Network ............................. 81

A2.4 Topologies Used in CPT to Implement the CCNA Security .......................................... 82

A3.1 Successful Exploit to Windows 2008 Server .................................................................. 83

A3.2 Resolving IP Address with DNS Lookup ....................................................................... 83

A3.3 BGP Peers and IP Route ................................................................................................. 84

ix
 LIST OF ABBREVIATIONS

ACL - Access Control List

AAA - Authentication Authorization Accounting
ASA - Adaptive Security Appliance
BPDU - Bridge Protocol Data Units
BGP - Border Gateway Protocol
CDP - Cisco Discovery Protocol
CCNA - Cisco Certified Network Associate
DNS - Domain Name System
DN Sec - Domain Name System Security Extensions
DMZ - Demilitarized Zone
DTE-DCE - Data Terminal Equip - Data Communications Equipment
DTP - Dynamic Trunking Protocol
EBGP - External Border Gateway Protocol
FTP - File Transfer Protocol
GNS3 - Graphical Network Simulator
GNOME - GNU Network Object Model Environment
GUI - Graphical User Interface
HTTP - Hyper Text Transfer Protocol
IP - Internet Protocol
ISP - Internet Service Provider

IIS - Internet Information Services

IDS - Intrusion Detection System
ISSAF - Information Systems Security Assessment Framework
IBGP - Internal Border Gateway Protocol
ICMP - Internet Control Message Protocol
JtR - John the Ripper
LSU - Louisiana State University
LAN - Local Area Network

x
MTU - Maximum Transmission Unit
NIST - National Institute of Standards and Technology
NAT - Network Address Translation
OSPF - Open Shortest Path First
OSSTMM - Open Source Security Testing Methodology Manual
OWASP - Open Web Application Security Project
PCI - Payment Card Industry
POP3 - Post Office Protocol
PSTN - Public Switched Telephone Network
QoS - Quality of Service
QEMU - Quick EMUlator
RAM - Random Access Memory
RIP - Routing Information Protocol
SQL - Structured Query Language
SSL - Secure Socket Layer
SMB - Server Message Block
SPF - Sender Policy Framework
SOA - Service Oriented Architecture
STP - Spanning Tree Protocol
TCP - Transmission Control Protocol
TLD - Top Level Domain
UDP - User Datagram Protocol
VPN - Virtual Private Network
VNC - Virtual Network Computing
VLAN - Virtual Local Area Network
VOIP - Voice over IP
WAN - Wide Area Network
WASC - Web Application Security Consortium

xi
 ABSTRACT

This thesis provides details of the hardware architecture and the software scripting, which

are employed to demonstrate penetration testing in a laboratory setup. The architecture depicts an

organizational computing asset or an environment.

With the increasing number of cyber-attacks throughout the world, the network security is

becoming an important issue. This has motivated a large number of “ethical hackers” to indulge

and develop methodologies and scripts to defend against the security attacks. As it is too onerous

to maintain and monitor attacks on individual hardware and software in an organization, the

demand for the new ways to manage security systems invoked the idea of penetration testing.

Many research groups have designed algorithms depending on the size, type and purpose of

application to secure networks [55].

In this thesis, we create a laboratory setup replicating an organizational infrastructure to

study penetration testing on real time server-client atmosphere. To make this possible, we have

used Border Gateway Protocol (BGP) as routing protocol as it is widely used in current networks.

Moreover, BGP exhibits few vulnerabilities of its own and makes the security assessment more

promising. Here, we propose (a) computer based attacks and (b) actual network based attacks

including defense mechanisms. The thesis, thus, describes the way penetration testing is

accomplished over a desired BGP network. The procedural generation of the packets, exploit, and

payloads involve internal and external network attacks.

In this thesis, we start with the details of all sub-fields in the stream of penetration testing,

including their requirements and outcomes. As an informative and learning research, this thesis

discusses the types of attacks over the routers, switches and physical client machines. Our work

xii
also deals with the limitations of the implementation of the penetration testing, discussing over the

vulnerabilities of the current standards in the technology. Furthermore, we consider the possible

methodologies that require attention in order to accomplish most efficient outcomes with the

penetration testing. Overall, this work has provided a great learning opportunity in the area of

ethical hacking using penetration testing.

xiii
 1. INTRODUCTION

How can any organizational network be tested for vulnerabilities in both software and

hardware aspects to analyze and potentially strengthen the security? How can a network be secured

from the hackers attacking routers and switches to manipulate the services?

This chapter addresses such type of questions with an overview for the need for network

security and essentials of penetration testing in the current world with the example network

breaches. We also consider the application of Border Gateway Protocol (BGP) and its

implementation as in the current internet systems. In brief, this chapter deals with the motivational

aspects and provides a brief layout of the thesis.

1.1 Pentester

The network security is one of the major concerns of any information system. As the size

of the system grows, the possibility of weak configurations increases which in turn create a security

loop hole. Security breaches create many complications. For example, recent Home Depot and

Target cyber security breaches have brought them a loss of approximately 60 million card numbers

to cyber thieves. Similarly, the network breach over JP Morgan’s bank in the recent past is likely

to cause a huge financial loss [18]. These incidents serve as a wakeup call to many big industries

all over the world. The need to secure networks for all the individual organizations, irrespective of

the size and purpose of the organization, has become much more important as it helps protect their

clients’ sensitive information and investments. Providing a secure networking environment against

offensive attacks is promising. The demand for the ability of an individual to test a network for

vulnerabilities has led to an evolution of a “Pentester” in the recent times [19], meaning a person

who performs penetration testing to analyze a specific network. Through penetration testing,

1
pentesters can help identify vulnerabilities/threats and provide the most dynamic way of protecting

certain networks [20]. Figure 1.1 illustrates this concept.

Figure 1.1: A Procedure Prototype for Pen Testing [40]

1.2 Border Gateway Protocol

Unlike other protocols in the routing systems, BGP is the called layer 4 protocol [38].

Current version of BGP being 4 is widely used by the ISPs for internal routing. BGP runs over

port 179 to establish a TCP connection. Note that BGP holds different kinds of protocols together

in a system of internet. One of the most concerned limitation of BGP is its high vulnerability [45].

Penetration testing on a network running BGP provides a most appropriate relation to the current

infrastructure scenario and also helps for future study.

1.3 Motivation and Thesis Layout

Networks have always been a part of all organizations’ infrastructure enabling software

applications such as file transfer, server features, website, etc. to run over it. In the present world,

2
irrespective of the size of the organization, networking capability has become an essential

requirement. For most people, awareness of networks is limited to having a wireless modem used

for household appliances. But without an individual’s interference, networks are preconfigured for

the mobile phones, desktop, laptops, etc.

Even though every household and organization involves networks and their applications,

there are a lot of concerns regarding their maintenance. One of the most typical but serious issues

that every network potentially needs to survive is the security breach. There are network intruders

everywhere, ranging from a neighbor exploiting an individual’s wireless setup to targeting

international banks and credit card companies for confidential information. For a person, a prior

knowledge of the network principles is important to ensure network security. Network engineers

and system administrators are always behind these loop holes in the network to spot and fix. But

not every flaw in any network is accessible to the network administrator as it requires deeper study

of the vulnerabilities and unfixed bugs.

This thesis is inspired by such security issues. The need for better understanding certain

network to be able to track down the bug is also a key motivation. There are many challenges in

understanding the knowledge-base of weakness and designing a robust network. To be able to test

a layout in parallel, study the vulnerabilities, pretentiously attack any network to practically

visualize the possibility of intrusion and to finally develop ways and means to provide a security

wall are few of those tasks.

Prototyping this kind of defensive mechanism on well programmed open source software

from major designers has become relatively understandable. There is a lot of research and equally

lot of experts who have developed systems to demonstrate a security assessment. With the help of

the pre-scripted modules from various developers, the job of testing a network has become much

3
more comfortable. The challenge to demonstrate this kind of infrastructure for performing

penetration testing is the main motto of this project. The following network assets count to be

major issues in our work;

 Challenge in deploying and creating a network infrastructure replicating real world

network using BGP protocol.

 Elaborating the study of vulnerabilities in such type of networks.

 Dealing with physical Cisco routers, switches, Linux and Windows servers.

 Exploitation and gaining access to test the stability of the weak network system.

1.3.1 Thesis Goal

In the field of penetration testing, considerable work has been accomplished to educate an

ethical hacker in building strong knowledge base using various online tools and virtual software

applications. This thesis is aimed to work beyond the software and provide a visually practical and

experimental implication of the tough tasks of designing network layout and performing tests. The

algorithms, layouts and the infrastructure presented in this thesis provide a bird’s eye view of how

a practical network is established with various entities. Also, this thesis focuses on how an attacker

could possibly attack the system and how a network engineer could protect the system. Usage of

BGP as routing protocol defines a complicated network setup. This work helps elaborate the

penetration testing in much more practical manner with more detailing in learning troubleshooting

techniques. This thesis would be a strong startup for the information base regarding penetration

testing, for students and also for beginners in penetration testing.

4
1.3.2 Thesis Layout

The layout of the thesis is as follows. Chapter 2 reviews the concept of penetration testing

in detail including a discussion on related tools and frameworks used. Chapter 3 deals with the

basics of BGP and also explains the relation to the project. Chapter 4 discusses the related work

including the previous achievements and the supportive research that have helped develop the

aimed concepts. Chapter 5 starts with the laying out of the network infrastructure and further

describes a systematic approach carried out to reach the goal with network layout sketch, screen

shots, configurations, code files and block diagrams. Chapter 6 involves a discussion about the

research contributions and the challenges faced during the experimentation, with appropriate

conclusion statements and likely enhancements of this thesis in future. Finally, Appendix 1 and

Appendix 2 provide details about configurations, topology and firewalls. We have also included

some additional screen shots for penetration testing in Appendix 3. Appendix 4 lists the description

of tools and frameworks used in this thesis.

5
 2. PENETRATION TESTING – AN OVERVIEW

Penetration testing is a process of systematic testing of hardware and software systems that

involve in creating a complicated network for data storage and transmission. It is a method of

understanding and evaluating the security ability of a network by simulating pretentious attacks

and exploits. This understanding helps in elaborating the depth of the security system of any

organization. This chapter considers all the different types of penetration testing based on the type

of approach and also on the type of concentration. An overview of the different phases of

penetration testing is described with block diagrams. Further, a description of the various tools that

a pentester used are briefly listed. Towards the end, objectives and benefits of this testing

methodology are explained.

2.1 Basic Concepts

“Penetration testing is the simulation of an attack on a system, network, piece of equipment

or other facility, with the objective of proving how vulnerable that system or “target” would be to

a real attack [24]”. This process is carried out by a potential ethical hacker. In simple words, it is

the procedural auditing of the security features of an established network or application.

Based on the type of approach, penetration testing is classified into three types [23], namely

Black box, White box and Gray box. Figure 2.1 illustrates the scope of this classification scheme.

This also narrows down the classification into two major types i.e. external and internal. In simple

words, it depends on whether the attacker system is inside the network or is targeting from outside

the network.

6
2.1.1 Black-Box

The Black-Box penetration testing is the most practical attack that a tester implements

without having any prior knowledge of the target systems. It is the most effective way to evaluate

a system for its security controls [23]. In simple words, the penetration tester would have no access

to any sort of information regarding the network, making a real world type of attack. This

eliminates the application type, location of the network, types of physical equipment, etc. The

attacker has to study the target completely from scratch in a systematic way to reach his goal. The

aim of the black box attack on a network is to study the cyber warfare attack completely.

Figure 2.1: Penetration Testing Layout [41]

7
2.1.2 White-Box

The White-Box provides a formal way of testing certain infrastructure as the tester is

provided all the basic information that understands the network layout, IP address and the

application details [22]. With this basic knowledge of the target network, the tester would be able

to infiltrate the network’s infrastructure with the key goal to mitigate the weak points. The tester

basically works from inside the network and establishes concrete base to setup a strong system. In

simple words, the tester and the organization work hand in hand to enable a tough security system.

2.1.3 Gray-Box

By the name, the Gray-Box is the combination of white box and black box types of

penetration testing. Here, the tester is partially provided with the target system’s infrastructure.

This type is not popular in the usual classification [23]. The available information may include the

server IP address or the source code of the application. The tester might not always test the system

from inside the network, rather pretend to be a hacker to test the robustness of the network

environment.

Furthermore, based on the assessment requirements, penetration testing typically can be

divided into four types [26]. Figure 2.2 illustrates this classification scheme.

a) Applications

Applications based penetration testing is mainly the focused on the vulnerabilities in the

data monitoring applications along with the firewall security issues. Also, the client-server

communication based applications that transfer information to sources might have critical loop

holes that count big for the target system. In the current scenario, a lot of major web-based

8
applications have wide proven vulnerabilities that are yet to be mitigated. These aspects are

concentrated while testing the network for its security using penetration testing.

Figure 2.2: Types of Testing Based on the Concentration [42]

b) Network

Network based penetration testing is one the major aspects in performing a testing over an

organization’s network. Based on the scale of the organization, the physical network might reflect

security gaps that usually go unnoticed during the setup. To ensure an unbreakable network and

maintain a strong back bone, penetration testing is performed on routers, switches, modems and

hubs to fill in the gaps. It is a process where a tester ethically attacks the network operations in an

organization to find flaws, vulnerabilities using exploits and aims to patch and fix the loop holes.

c) Physical

The scope of weakness in this area would be the unauthorized physical access to the target

machines in an organization. Authentications and restricted access are thoroughly reviewed and

tested while dealing with the physical technique penetrating testing. This plays a major role as it

9
helps gather information of the target system in a much more comfortable way of physically being

inside the network. This is concentrated to synthesize the effectiveness of the authorization

authentication and access to the physical systems.

d) Social

Social engineering targets on the social websites that can easily be reached using Google

and other engines. With the high social exchange over websites like Facebook, LinkedIn and

Twitter, a huge amount of information is being shared that could be a starting point of the attackers

to build on. Also, public meetings, human interaction are the main weaknesses that are focused on

by the attackers [25]. This particular field of penetration testing is useful to evaluate the

unauthorized access to the confidential information.

2.2 Systematic Approach

A successful penetration testing methodology is the integration of a step by step procedure

that a tester has to follow. Our work is illustrated in the same manner as the steps involved in this

methodology. Figure 2.3 illustrates these steps.

Figure 2.3: Step by Step Pen Testing [43]

10
 From the figure, the steps can be further amortized into six stages for better understanding

as follows:

2.2.1 Planning and Preparation

Depending on the type of the penetration testing, planning and preparation is the first phase

and could be a general meeting among the owners of the organization and the testers or a complete

background of the target network. This is usually the approach a tester follows to familiarize the

organization regarding every single approach and method that would be involved during the

procedure with a lucid aim and scope [27]. Simply it’s the phase where the tester gets to know

about the target system’s background and scales his methodologies with a major objective to

exploit all possible vulnerabilities and provide a mitigation method to most of those with genuine

detailing. This agenda also involves the privacy policy agreement, deadlines, and scheduling.

2.2.2 Information Gathering and Analysis

This phase, otherwise called as “Reconnaissance,” involves gathering information

regarding the target. With the knowledge acquired during the planning and preparation phase, the

tester in this phase sets a platform to gather network and application information of the

organization’s system as much as possible. This phase needs clear understanding with proper

management so as not to consist of intuitions and guesses. This phase plays a major role in the

penetration testing as the amount of information gathered would be proportional to the amount of

successful exploits. The main aim of this phase is to analyze the network layout for IP addresses,

server names, applications that maintain a database, contact information, and study possible

vulnerabilities based on the software [28]. The information can be gathered using the online

sources that involve news channels, websites, social media and also by using Linux tools.

11
 This can be further divided into passive and active based on the method of acquiring

information. Passive is when information is gathered by searching online and researching on the

background of the organization, without interfering with the organization itself. Active is when the

process involves the interaction with the organization like banner grabbing.

For example: If the target system is LSU, the attacker can very easily find out the website

on Google by just making a search about LSU. With the website, getting the server name, domain

names, Internet service provider, the IP address and the range of the host names, operating systems,

database application and the security level can be analyzed using a variety of open source tools

that are available free of cost online. We shall discuss more about this in the following pages of

this write up.

2.2.3 Vulnerability Detection

This phase is otherwise termed as Scanning, as it involves scanning the network based on

the information that is available and the respective tools. Elaboration of this phase completely

depends on the tester as the vulnerabilities of operating systems and applications are always

existing, and the manufacturer works to fix these bugs from time to time. A detailed knowledge of

the vulnerabilities in various platforms is very essential to perform this phase successfully [29]. It

can be further divided into three major areas based on the type of scanning that is being performed

[30].

i) Network Scan

This area concentrates on knowing information regarding all the host machines that are on

the network. This scan involves scanning the network’s server to gather information of individual

hosts on the network. This scanning helps the tester identify the IP address, operating system, and

server information. Ping sweep is the most general way to accomplish this type of scanning.

12
 ii) Port Scan

Once the tester acquires information about a specific host, the port scanning helps identify

the open ports on the system and the applications that are actively taking part in the host

maintenance.

iii) Vulnerability Scan

This scan helps spot possible vulnerabilities in the host machine’s operating system or the

server applications or the ports that are open for the various protocols.

Scanning phase paves a path to be able to perform attacks on the vulnerable system and/or

network.

2.2.4 Penetration Attempt

Here the tester accumulates all the possible packages that suit for exploitation of the type

of the vulnerabilities examined during the vulnerability scan. With the scans resulting in open

ports, application designers, and operating system information, the tester sends out exploits

followed by payloads to run on the host machine timely to ensure the success of the exploitation

[31]. During the process, the tester has to populate the packages with all the available information

including the target machine’s IP address. The successful exploitation brings a consensus on the

security level of the organization’s network layout.

2.2.5 Analysis and Reporting

If the penetration testing is performed officially for an organizational purpose, clean

documentation needs to be provided as the result of the process. This is termed as the Analysis and

Reporting phase, wherein the tester lists down all the procedures and methodologies that were used

to perform all the above phases including the mitigation and security level scoring. This

13
documentation comes in very handy to analyze the vulnerabilities and watch for attacks over these

for expanded security. Also, for future reference this would help in the information gathering

phase.

2.2.6 Cleaning Up

After the whole procedure of exploring vulnerabilities and providing a mitigation

methodology, a reverse procedure to clear all the modifications is mandatory, as the organization

would not want any trace of the path paved towards vulnerabilities and the applications that are

run on the target systems. This is basically undoing the setup, demonstration and exploitation.

Implementation of this systematic approach helps achieve the most efficient penetration

testing outcome.

2.3 Tools and Frameworks

For the purpose of offensive security, there are many tools out in the market that help

penetration testers and network managers to test and build a secure network layout. Most of them

are free, open source tools developed for the purpose of ethical hacking and are specifically

designed for usage with Linux machines. Different phases of penetration testing can be

accomplished using suitable tools. There are scanning tools, testing tools, working platforms,

vulnerability detection tools, etc. Among those are the list of the tools in Table 2.1 that we have

used to demonstrate this security assessment. A detailed description of their usage and sources are

tabulated in Appendix 4.

14
 Table 2.1: Tools

No Tool Reference Type

1. Brutus [10] Password cracker

2. Dradis [48] Scan report organizer

3. DNStuff [11] DNS report generator

4. Hydra [49] Password cracker

5. Hping [13,14] Packet crafter

6. John the Ripper [17] Password cracker

7. Kali Linux [1] Offensive OS

8. Metasploitable [50] Vulnerable OS

9. Metasploit [2,3,4] Security project

10. Maltego [51] Network visualizer

11. Nmap [7] Network scanner

12. Netcraft [8] Scanning Website

13. Nessus [15,16] Vulnerability scanner

14. Netcat [12] Network utility

15. Python [52] Programming language

16. Scapy [53] Packet crafter

17. Ubuntu [6] Linux flavor

18. Wireshark [54] Packet analyzer

15
 Also, there are various frameworks that pentester adapts for security assessment. These

frameworks are widely accepted as they meet requirements of industry standard frameworks [34].

Table 2.2 lists the most commonly used frameworks.

Table 2.2: Frameworks

No Framework Reference Type

1. WASC [34] Web Application Security Consortium

2. OSSTMM [34] Open Source Security Testing Methodology Manual

3. OWASP top 10 [34] Open Web Application Security Project

4. ISSAF [34] Information Systems Security Assessment Framework

5. NIST [34] National Institute of Standards and Technology

Also, some of the most widely assessed vulnerabilities using these frameworks include the

following [34].

 Sql injection

 Hidden backdoors

 Cross site scripting

 Cross test request forgery

 Command injection

 Bypassing authentication

The above listed vulnerabilities are difficult to trace but are inclined to the absolute usage

of frameworks. Most network security companies employ pentesters based on their ability to

exploit these vulnerabilities.

16
2.5 Objectives and Benefits

Penetration tests on a large scale are beneficial in tracing critical vulnerabilities on any

organizational network, helping individual companies to either advance their technology or

enhance the security by mitigating the loop holes. The main objectives of a successful penetration

include security incidents identification, determining the ease of the vulnerable aspects, and

examining the extent of reachability. Benefits include proving the status of network infrastructure

with detailed reports and identification of critical network points that are attack prone. These tests

performed regularly protect an organization’s security potential [37].

2.6 Conclusion

Penetration testing on the whole is a creative invention, upholding the network security.

Collaboration of the built in packages in the various tools on a suitable platform will help testing

procedure have a robust impact on any network. With quality objectives and supportive

environment, penetration testing is surely the highest level of network security assessment. A

complete penetration testing methodology is the one that follows a systematic approach. We in

this thesis follow this procedure aiming to ethically gain access to different operating systems to

demonstrate a pentester’s view of network security assessment. Though the penetration testing

displays limitations of data loss and the domain chaos, these completely dependent on the pentester

and not the procedure itself.

17
 3. BORDER GATEWAY PROTOCOL

BGP is an abbreviation for Border Gateway Protocol. It is an inter-domain (layer-4) routing

protocol also termed as distance vector protocol. The concept is to divide the large Internet into

small autonomous systems enabling efficient routing [32]. In these autonomous systems, the layer-

3 routing scheme is used to carry the datagram. BGP connections run on port 179 TCP. Exterior

gateway protocol is predecessor to BGP. Based on the links between routing equipment, BGP is

classified into two kinds [32]. Figure 3.1 illustrates this concept.

Figure 3.1: Scope of BGP

IBGP: This is called Internal Border Gateway protocol and describes the running of BGP

internally within an autonomous system (AS).

EBGP: This is called External Border Gateway protocol and describes the running of BGP

between two different autonomous systems.

18
3.1 BGP Attributes

BGP attributes lie in the details of its path attributes and the types of messages peers

exchange during connection establishment.

3.1.1 Path Attributes

Path attributes used in BGP are based on the type of functionality and are as follows [47].

Origin: This defines the origin of the routing information. It comprises three values: 1, 2

and 3, based on the information learned from the intra-domain routing such RIP or OSPF, or

learned from other BGP or learned from an unknown source.

AS-Path: This defines the list of autonomous systems that fall in the path from source to

destination.

Next-Hop: This defines the next router in the path to which the data packet is being

forwarded.

Mult-Exit-Disc (MED): By the name, this is used to define multiple exit paths to a

particular destination. The lowest MED is prioritized.

Local_Pref: This value is defined by the administrator depending on the routing policy

being implemented. Preference assigns values to the routes.

3.1.2 BGP Messages

BGP4 establishment typically undergo four types of messages for communication among

the Autonomous systems [33]. These messages are shared between the BGP peers in the process

of establishing a route in the network. Each message has its own specific meaning resembling a

phase of the interface. Figure 3.2 illustrates the same in a flow chart manner.

19
 Figure 3.2: The Process of BGP Connection Establishment [44]

Open: BGP opens a TCP connection and sends an open message to ensure neighborhood

relationship. Once a router receives open message, the router evaluates authentication, autonomous

system number, etc. Unless the information carried is erroneous, a keep alive message is sent back.

Notification: The BGP speaker sends out a message whenever there is an error in

connection establishment. It could be regarding the autonomous system number, IP address error

or anything else.

Update: The update message is for the router to withdraw destinations that have already

been advertised. As the router receives an update message, it automatically updates the BGP

routing table.

Keep Alive: This message is the code of confirmation among the BGP speakers to

advertise as still alive. A router ends BGP session if it doesn’t receive a keep alive from a neighbor.

20
3.2 Conclusion

With this brief study of the Border Gateway protocol, the importance is well understood.

Its application in this thesis is seen in Chapter 5 of implementation. We have used BGP as the

major routing protocol in the network for penetration testing. The reason for choosing BGP is its

application on the Internet. Also, BGP is widely used in the current routing mechanisms, making

it the best suite to replicate the real world scenario. Furthermore, the vulnerabilities, like intercept

Internet traffic discovered in BGP makes its application more interesting for future work [46].

21
 4. RELATED WORK

With the aim to research on the security configurations and applications over Cisco devices

in a LAN/WAN/VLAN network, we have studied and worked with three major Cisco tools. To

test security features on router, switch and firewall using virtual machines, these tools are the best

way to start off. The following are the tools that were initially reviewed to work virtually with

Cisco equipment.

 Cisco Packet Tracer

 Graphical Network Simulator

 Cisco Configuration Professional

4.1 Cisco Packet Tracer

We have used Cisco packet tracer to define the CCNA security terms and the mitigation

algorithms over a switch and a router. The security is aimed to defend against the attackers. The

attackers are both from inside and outside of the network. Attacks from outside are basically kinds

like brute-force, password hacking, etc. The attacks from inside are also of huge concern. Possible

threats from inside the network could be as follows.

 Usage of switches included in the network

 Accidental usage of an infected laptop

 Enabling remote communications that open a hole for broadcasting

 Attacker is adding a switch or wireless access point.

These can be widely classified into two major attack types: (a) Access attacks to switch/router and

(b) LAN attacks.

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4.1.1 Access Attacks

These include the type of attacks that let the attacker access the devices through the

management loop. Switch/Router access control security needs to be enabled to secure the devices

inside of any network. A detailed analysis of the basic access attacks is as follows.

Firstly, AAA framework is key to improve the client side security to restrict unauthorized

access. AAA stands for Authentication, Authorization and Accounting [57].

i) Authentication

This deals with the individual’s user accounts and passwords, providing authentication to

gain access to the equipment.

Router (config) # username ******

Router (config) # username ****** secret *******

ii) Authorization

This deals to set different levels of privilege depending on administrators and the users

enable privilege level 15.

Router (config) #ip access-list standard 1

Router (config) #permit **. **. **. **
Router (config) #login quiet-mode access-class 1

iii) Accounting Logging

This helps to log all the login attempts on the asset from start to shut, providing a way for

the administrators to maintain continuity files for security.

Router (config) #login on-failure log

Router (config) #login on-failure log

23
 Further, there are also other aspects such as physical security, password complexity, and

Ethernet port security that help secure a network setup. Though these seem to be trivial, for an

attacker this acts as an extra layer of penetration.

iv) Physical Security

This provides security at the console port with a password to enable the router.

Router (config) #line console 0

Router (config-line) # password ******
Router (config-line) # login
Router (config-line) # no login
Password encryption and strength provide a perfect complexity to decrypt and crack

helping to maintain and restrict users having weak passwords.

v) Encryption

“Show run” command in the usual scenario displays the password that is being used to

login into the console and others. Encryption is required to have a strong password. Md5 and level7

security can be used for this purpose as follows.

Router (config) # service password-encryption

This enables type7 encryption. But type7 is not secure anymore as there are open source

tools and websites that easily decrypt this sort of encryption. On the other hand, md5 encryption

is much more secure.

Router (config) # enable secret *********

vi) Strength

To have more specifications over the password to have a minimum number of characters

including case sensitive and symbols usage, the following needs to be configured.

Router (config) # security passwords min-length 10

The above sets a minimum length for password choice that the user needs to set.

24
 Further, timeout on the router can be modified from the default of 10 minutes to 4.

Router (config-line) # exec-timeout 2

Router (config) # login block-for 180 attempts 5 within 120

Login attempts are configured as above setting a limit to 3 minutes for a maximum of 5

attempts within 120 seconds to have more severe strengthening of logging. This fights against

brute-force and dictionary attacks.

vii) Ethernet Port

Lastly, to remotely access into the router using telnet/SSH/AUX, a few configurations on

Ethernet help maintain credible security. Also setting the enable password helps,

Router (config) #line vty 0-4

Router (config-line) # password ******
Router (config-line) #login
Router (config-line) # enable password ******

4.1.2 LAN Attacks

For this record, we have considered the LAN attacks on layer 2. The type of attacks that an

attacker might aim at weak LANs are VLAN hopping, spoofing attacks, DHCP attacks and ARP

attacks. To restrict this type of attacks the following individual ports configuration helps.

i) DTP and VLAN Configurations

Attackers try to get access to a switch to jump to other VLANs on the network. These type

of attacks let attackers broadcast domains. To not let attackers hop DTP is disabled.

DTP, in most of the Cisco devices, is automatically enabled. DTP allows ports to auto

negotiate into auto mode into the trunk. If an attacker identifies this trunk, connection to the port

and sending trunking protocol automatically lets switching into the trunk.

Switch (config) #interface range fa0/1-24

Switch (config-if-range) #switchport mode access

25
 Manually configuring modes for access, will not let ports turning into trunks. Trunking

also will be turned off by this negotiation. And creating VLAN25 which is unused, makes the

guess of the VLAN ID much complicated.

Switch (config-if-range) #switchport access vlan 25

It is suggested to not use default VLANs, but, by default all Cisco switches start as

members as manage VLAN and native VLAN in VLAN1. We need to move VLAN1. Configure

switch ports to not be configured to VLAN1. Native VLAN1 is used for backwards compatibility.

VLAN hopping technique is double tagging. When a packet goes from native VLAN trunk, VLAN

ID is stripped from the packet. If you have 2 IDs, the first will be stripped, the second will remain

and now the packet ends up on the other side with the 2nd ID.

ii) STP

STP is enabled by default on the switches. When we have multiple switches and have the

possibility of switching loops, attacker could manipulate packets and configure STP to become

Route Bridge to get all spanning tree configurations.

Switch (config-if) #spanning-tree portfast

Switch (config-if) #spanning-tree bpduguard enable

Access ports need portfast enabling to allow to move from blocking to forwarding mode

with listening and learning. So, “bpduguard” will shut the bpdu not to make the ports trunk.

iii) CDP

CDP is enabled by default. It is a layer two protocol, with a lot of information of

neighboring switches. It can be used as reconnaissance to find out about other switches and routers.

26
We need to disable CDP by default. The following command will shut down CDP. CDP is useful

only for VOIP in GNS3.

Switch (config-if-range) #no cdp enable

Switch port security is necessary to help defend against broadcast storm. Addition of storm

control measures that will broadcast all switch ports will cause DoS LAN broadcast storm attack.

Storm control is disabled by default, so we need to enable it. From the command below, if

broadcast packets go past 70% of available bandwidth, the port will shut down.

Switch (config-if-range) #storm-control broadcast level 70

iv) Port Security

Mac Address spoofing is someone imitating mac address of other devices on the network.

Port security will enable only one mac address allowed.

Switch (config-if-range) #switchport port-security maximum 3

Switch (config-if-range) #switchport port-security violation shutdown

This configuration shuts down the port. It will also protect/restrict further access to the port

until reconfiguration.

Mac address overflow attack is when the switch is allowed to be bombarded with packets

and mac address, the switch will try to save in the table with too much information piling up

causing overflow. This broadcasting of all ports, making it a hub for the attacker to all ports causes

an overflow attack. Allowing only one mac address with no new devices will help restrict this

attack. Port security is disabled by default. We need to enable it.

Switch (config-if-range) #switchport port-security mac-address sticky

27
 This helps enable the switch to remember or learn on the port. Also to age switch out, the

following has to be configured.

Switch (config-if-range) #switchport port-security aging time 200

v) Trunking Ports

To turn the ports into trunks manually and allow to go across these trunks. Also, to set

native vlan to VLAN91 instead of VLAN1, the following is configured.

Switch (config-if-range) #switchport mode trunk

Switch (config-if) #switchport trunk allowed vlan 20,60,40,91
Switch (config-if) #switchport trunk native vlan 91
Switch (config-if) #switchport nonegotiate
Switch (config-if) #spanning-tree guard root

The above configuration helps enable root guard on STP root ports which in turn help to

protect Root Bridge. If packets are sent to switch for bpdu use, do not allow it.

Hence, we have achieved manually configure all user ports, trunk ports and port security

on access points, enable portfast, BPDU guard on all access ports and root guard on STP root ports,

disable unused ports, DTP on all trunk ports, CDP on all ports. All these functionalities can be

visualized on the CLI using “show interface” command.

4.2 Graphical Network Simulator 3

We have used this particular tool to configure ASA and build a topology to visualize the

working of the firewall practically. Adaptive security appliance is a multipurpose firewall. The

ASA firewall denies traffic that is coming from outside.

28
 Three major features are as follows [56].

 Stateful inspection, this is when a user goes onto a website online, the ASA firewall

remembers the user’s information in a Stateful session table and checks with the reply that

is coming from outside. It is not going to deny this reply and allow communication.

 Packet filtering functionality on ASA firewall allows traffic from the exceptions made on

it.

 VPN support (SSL/IPsec): This helps build a VPN to protect the confidentiality of the data

traffic that is being transferred over the network.

Usually, the default security levels of the inside and the outside setup of the network are

100 and 0 with ASA firewall.

In building ASA firewall on a topology, we have used GNS3 (graphical network simulator)

to be able to use a virtual PC simulator. Also, the console in the GNS3 is putty by default. We

have preferred using secureCRT for this process. Once the installation of GNS3 is accomplished,

the IOS images for the router 2600 and 3700 have been deployed.

4.2.1 ASA Configuration

The test settings are checked to be successful under the QEMU settings on the GNS3

application to enable ASA firewall on GNS3. On ASA tab, with a name, RAM, initrd and Kernel

files have been deployed. Followed by feeding the QEMU options and Kernel command line [21]

with the following respectively.

 -vnc none –vga none –m 1024 –icount auto –hdachs 980, 16, 32

 -append ide_generic.probe_mask=0x01 ide_core.chs=0.0:980,16,32 auto nousb

console=ttyS0,9600 bigphysarea=65536

29
 After the deployment of ASA firewall on GNS3 tool, SecureCRT is enabled.

Next, we have a virtual PC simulator that comes with the GNS3 package. Installing and

operating virtual machines on this tool is just like any other virtual machine. All the settings on

the virtual machine are configured prior to that of simulating the topology as the changes in the

virtual box would only be reflected on the tool after a system reboot.

For the topology we have chosen, four virtual PCs with windows XP, Ubuntu and two

windows 2003 R2 servers are involved. These machines are left disconnected from the Internet

and the networking addresses on these are configured to be working on the topology. The addresses

include IP address, DNS information and the gateway through the network settings. Also, the

virtual Host-only Ethernet Adapters are manually added to reflect on to the main system that which

is running GNS3. Also on the network settings in the virtual box, the Network adapter is manually

configured using the same notation as in the main system to maintain synchronization.

With successful configurations of GNS3, Virtual box, secureCRT setup and ASA

configuration, the topology is built. In a basic ASA, the three zones that involve to describe it most

effectively are the LAN, WAN and DMZ [56]. With LAN counting to be the inside network, WAN

as the outside network and the DMZ as the Demilitarized Zone. LAN and DMZ interfaces on the

virtual box are setup with the proper coordinative configurations.

To build the topology on the GNS3, drag the ASA firewall, routers 3700, Ethernet switches

and clouds. Clouds are used as media of communication for the host machines to the devices. The

three clouds are named LAN, WAN and DMZ, respectively. Further, we have the configuration

on these nodes with the Ethernet ports on the main machine to sync with the machines that we are

looking forward to communicating with. Once all the elements are brought on the workspace on

30
GNS3, the connections with the proper orientation are made using the regular cable. The console

ports on the devices and the ASA device have been synchronized on the secureCRT accordingly.

Similar to that of the Cisco Packet tracer, once the topology is ready, debugging and

configuration is followed. Configuration steps on ASA are as below.

Ciscoasa >enable (to enable the ASA)

ciscoasa # configure terminal (get to the ASA privilege mode)
ciscoasa (config)#hostname ASA ( give a name to ASA)
ASA (config)# mkdir (creates a directory)
ASA (config)# mkdir NAME (names the directory)
ASA (config)# copy running-configuration disk:0/NAME/(copies conf on that directory)
ASA (config)# copy disk0:/NAME/running-configuration disk:0/NAME/startup(to launch
on start-up
ASA (config)#boot config disk0: /NAME/startup (this is saved and on startup)
ASA (config-if)# interface e0
ASA (config-if)# IP add 10.1.0.254 255.255.255.0
Similarly, configure the other two interfaces on ASA with
ASA (config-if)# IP add 192.168.5.254 255.255.255.0
ASA (config-if)# IP add 100.1.0.254 255.255.255.0
ASA (config-if)# nameif inside (to determine the security level of inside network as 100)
ASA (config-if)# security level 40 (manually assigning security)
ASA (config-if)# nameif outside (to determine the security level of outside network as 0)

Enable the http on the machine to be able to work with the ASDM.

ASA (config-if)# http 0 0 inside (to enable all the inside networks for http from remote host)

And further configure the routers on the topology as follows

31
 IP address on R1 is a

 200.0.0.1 on fa0/0
 250.0.0.1 on fa0/1
Similarly, on R2

 250.0.0.2 on fa0/1
 150.0.0.2 on fa0/0
Now that the devices and the clouds are configured, the ping from any of the systems in

the topology would successfully ping the machine. Be it the DMZ to LAN (or) DMZ to ASA (or)

LAN to ASA. Also with the security features configured on the firewall, the incoming traffic is

managed in synchronization to that of the outgoing traffic.

Further, to manage the ASA firewall using ASDM is also determined. Initially, transfer the

ASDM image to ASA so that ASDM running on the computer can manage ASA.

“Copy tftp flash:” (command to copy ASDM image)

“Show flash:” (to check the flash for verification)

To set this image for the ASA use “asdm image flash:”. ASDM is on a virtual machine to

check the communication and further manage. Startup wizard, configuration of interfaces and

specifications would finish the setup with privilege authorization. The NAT/PAT, AAA rules

along with the filtering servers, etc., are modified and tested over the ASDM.

Now on the browser in LAN, the IP address with HTTP enabled, lets ASDM run on the

browser. This indicates and enables configure the ASDM to be able to manage ASA. Further, the

ping from the DMZ and the LAN interfaces have been checked.

32
4.3 Cisco Configuration Professional

This is a real time tool that lets the administrator configure Cisco routers manually without

having to use the command line. It is more dynamic and easy.

It offers the following features [39]:

 One-click router lockdown

 Innovative voice and security auditing capabilities to check and recommend changes to

router configurations

 Monitoring of router status

 Troubleshooting of WAN and VPN connectivity issues.

The two major concentrations are monitoring and configuration of the devices. Through

the configuration tab on the tool with the devices connected, we can configure an interface, manage

security criteria over the router, or configure voice and monitor.

4.3.1 Configure

 Interface configuration: interfaces, serial, DSL, analog and digital trunks.

 Router configuration: hostname, banner, static and dynamic NAT, QoS, net flow, dynamic

and DNS.

 Security configuration: Security firewall and ACL, VPN, AAA, web filter.

 Voice Configuration: telephone settings, voice mode, PSTN, dial plans and firmware.

33
4.3.2 Monitoring

Monitoring checks the current status of a router and manages the routers by picking the

devices. This will provide an overview of the router with memory utilization and the firewall and

security features. We have implemented the same topology as that of the GNS3 with minimum

devices to work on the ASA firewall and the advanced security options.

We have used this tool to perform the basic security tests on the Cisco equipment. The aim

was to enhance security in a network over VOIP, INTRANET, and INTERNET. Further, aimed

to deploy and decide on the best security methodologies.

All the screenshots of topology and working environment related to this chapter are

displayed in Appendix 2.

34
 5. IMPLEMENTATION

A detailed description of the laboratory results of the penetration testing phases explained

in the introductory chapters will be discussed in this chapter. This involves screenshots of different

stages of performing tests with appropriate description. Implementation of BGP to design a

working laboratory network is illustrated. Also, the steps involved in different stages of the

network penetration testing procedure will be explained using python scripts, socket programming,

and command and screen captures of various tools with a detailed lab infrastructure setup.

For the purpose of application penetration testing, we have considered elaborating one case

of using Windows XP as the target machine. The rest of the operating systems and the exploits

that we have worked on are attached in Appendix 3.

5.1 Laboratory Setup

A network lab is setup which has multiple routers, switches and operating systems. Cisco

1841 and 2611 series routers and Cisco 2950 switches are used in the Lab. A WAN network

environment is designed by connecting serial interfaces on routers using DTE-DCE Cable and T1

RJ48C cables, respectively.

Figure 5.1 shows an infrastructure replicating a real world organizational network layout

set using BGP routing protocol involving autonomous systems. It can be clearly observed that the

topology involves both IBGP and EBGP configurations amongst the peers. Individual machines

and Cisco equipment are configured as indicated in the Appendix 1. Also, configuration steps,

BGP peers and IP routes are shown in Appendix 3. For this lab, we have used BGP-4 as the running

protocol on the routers as BGP is currently used by both ISPs and local networks.

35
 Figure 5.1: Lab Topology for Demonstrating Application Attacks

Since it is a lab infrastructure, having a domain with a world wide web was not possible

for various reasons. So we have configured local domains on Windows server 2003 and Windows

server 2008 machines. Routers and switches are configured with the basic network configuration

commands using BGP involving three autonomous systems as shown in the figure using hyper

terminal. These devices with the computers form a network and are checked to ping each other. In

the lab setup, Linux and Ubuntu machines are attacking machines, and the rest of the Windows

operating systems and Metasploitable are the victims.

Figure 5.2 and Figure 5.3 are the other network topologies we have used for better

understanding of the basic network security features and routing protocols. Utility of Cisco 2600

routers is predominant in these two assessments.

36
 Figure 5.2: Lab Topology for Layer 3 Penetration Attacks

Figure 5.3: Lab Topology for Layer 2 Penetration Attacks

The routers and host machines in Figures 5.2 and 5.3 are configured as displayed in the

respective figures.

37
 Figure 5.4 is displays the actual setup in the laboratory. This clearly shows various

desktop machines, routers, switches, cables, etc. Starting top left, Windows 7 laptop, 1841

routers stack showing front panel, Windows XP desktop, Ubuntu 12.04 desktop, Windows 2008

Server, Windows 2003 Server, Kali Linux desktop, Routers showing the connections made using

RJ48 straight through cables and the panoramic picture of the lab. This panorama also includes

Cisco 2950 switches, Cisco Catalyst 7000 series routers that we have used for understanding

purposes.

Figure 5.4: Actual Laboratory Setup

38
5.1.1 Procedure

 Connect the routers using suitable cables.

 Connect the LAN interfaces of the routers to the appropriate switches.

 Connect the PCs to the switches.

 Configure the IP addresses for the PCs and the routers as detailed.

 After successful configuration, the PCs should be able to ping each other.

Note: The configuration for the 1800 series routers and 2600 series is different as the

interfaces vary and so does the Cisco OS. The following steps explain a basic router configuration.

Router Configuration Outline

Router>enable # Go to the enable mode on the router

Router#configure terminal # Go to config mode
Router(config)#hostname R1 # Configures the hostname as R1
R1(config)#interface fastEthernet 0/1 # Go To the LAN interface of the router
R1(config-if)#IP address 192.168.1.1 255.255.255.0 # Configures the IP address
and subnet mask
R1(config-if)#no shutdown # Enable the interface
R1(config-if)#exit # Exit from interface mode
R1(config)#interface serial 0/0 # Go to the serial interface of the router
R1(config-if)#IP address 10.0.0.1 255.0.0.0 # Configures the IP address of the
interface
R1(config-if)#clock rate 64000 # Configures the clock rate as this is the DCE end.
R1(config-if)#no shutdown # Enable the interface
R1(config-if)#exit # Exits from the mode
R1(config)#IP route 192.168.2.0 255.255.255.0 10.0.0.2 # Configures a static
route for reaching the 192.168.2.0 network from the 192.168.1.0 network.

Also, for routers to enable and assign BGP and its peers, the following needs to be

configured.

R1#conf t
R1(config)#router bgp AS-num
R1(config-if)#neighbor **.**.**.** remote-as AS-num
R1(config-if)#network **.**.**.**

39
 PC Configuration

The TCP/IP adapter of the Linux and Windows PCs are configured as shown in the

topology, with an IP address, subnet mask and default gateway. These are configured accordingly

based on the operating system as it is completely different.

In a Windows PC, TCP/IP network adapter is configured directly from the control panels

listing. Whereas in a Linux based machine the configuration of IP address is done with the

following command in the terminal, followed by editing the script.

$ sudo nano /etc/network/interfaces

5.1.2 Tools and Services on PCs

This section lists down the various tools and frameworks that are deployed operating

systems to conduct the experimentation.

Ubuntu
 Hping
 Scapy
 Python
Kali Linux
 Nessus
 Maltego
 Dradis
 Metaspolit
Windows XP
 Hyper terminal
 Wireshark
 Tftpd 32 server
 .Net framework
 Mssql
 SSMS

40
Windows 2008 Server
 Active Directory Domain Services
 DHCP Server
 DNS Server
 File Services
 Web Server (IIS)
Windows 2003 Server
 Active Directory Domain Services
 DHCP Server
 DNS Server
 File Services
 Web Server (IIS)

5.2 Network Penetration Testing

This is the back end study of a network that involves analysis of routers and switches and

their vulnerabilities. This study understands the penetration testing methodology for testing

different types of layer 2 and layer 3 attacks and vulnerabilities on a network using packet

generation and crafting tools like Hping, Scapy, and python. The anatomy of different types of

layer 3 attacks like TCP Syn flood, Land attack, IP Spoofing and layer 2 attacks like cam-flooding,

mac-spoofing and STP based attacks are understood. The code/script that is required to generate

the attacks with the appropriate tools is analyzed. Security features like ACL, port-security, STP

BPDU Guard and configuration required to defend against the attacks are verified. A lab

infrastructure is set with Cisco routers and switches, where the WAN network environment is

simulated using T1 and DTE-DCE cables on Cisco routers and with multiple LAN networks. One

LAN network would be used for generating the attacks, and the other WAN network would be

used to analyze the anatomy of the attacks using packet analyzers like Wireshark and router/switch

console outputs.

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5.2.1 Layer 3 Assessment

In this section, we provide a detailed description of attacks that are possible over a Layer

3 routing network along with the defense mechanisms. The whole assessment is in reference to

Figure 5.2 topology.

i) TCP Syn Flood Attack

The following code is executed from the Ubuntu system, using hping3 on the command

line. The code would simulate a TCP Syn flood behavior, to the web server (IIS), which is set and

configured on the Windows XP system. Wireshark on Windows XP is started for analyzing the

packets that are sent using the code displayed in Figure 5.5.

Figure 5.5: TCP Syn Flood Attack Script

Code explanation is as follows,

 Sudo starts hping3 with admin privileges.

 –p 80 crafts the TCP segment with the destination port as 80, as a web server (IIS) runs on

port 80 in Windows XP.

 –S sets the syn flag in the TCP header. This is for crafting the TCP SYN segment.

 –c 10 sets the count as 10. The crafted TCP SYN segment would be sent ten times to the

destination that is 192.168.2.2. This can be specified as per requirement.

 192.168.2.2 Specifies the destination or the target, which is 192.168.2.2, the Windows XP

system.

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 In Figure 5.6, the first frame (No 89) shows the first TCP SYN segment, which is sent. It

can be observed that the SYN bit is set with the source IP address as 192.168.1.2 and destination

IP address as 192.168.2.2. The second frame (No 90) corresponds to the TCP SYN/ACK segment

which is sent from the IIS server to the TCP SYN segment. This is the second stage of the TCP

three way handshake. It can be observed that the goal of the attack is to keep half open connections

of TCP, and not complete the three way handshake thus attempting to exhaust the maximum

number of TCP connections allowed on the server.

Figure 5.6: Wireshark Analysis on the Victim

Note: The Wireshark capture also shows TCP [RST]. This is not part of the TCP Syn flood attack.

This is sent from the Ubuntu system, as there is no valid TCP ACK, which is required to complete

the three way handshake.

Defense

Wireshark analysis provides knowledge of the attacker’s IP address. An access control list

is configured on the R2 router, which would block packets originating from the source,

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192.168.1.2, on the serial interface of the router. This makes the attacker IP address malicious. The

details of the configuration are provided below.

R2 (Configuration)

R2(config)#access-list 10 deny 192.168.1.2

R2(config)#access-list 10 permit any
R2(config)#interface serial 0/0
R2(config-if)#IP access-group 10 in

The first line from the configuration creates a standard access list, with the number 10,

which denies IP traffic with the source address 192.168.1.2, which is the attacker’s address. The

second line allows all other traffic in the access list. This is followed by applying an access list on

the serial interface as inbound.

Verification

Once the ACL is configured, an attempt to attack fails as the packets being filtered as

shown in Figure 5.7 below. The ACL does not allow incoming traffic with the source IP as

192.168.1.2. Analysis by Wireshark will also indicate the TCP packets not reaching the server.

Figure 5.7: Output Indicating Defense to TCP Syn Attack.

TCP Syn flood can also be sent using a DDOS model, where the TCP SYN segments are

sent from multiple systems. As the source IP addresses change randomly, appropriate security

44
features would be required to mitigate the attack. The TCP intercept feature can be used for this

purpose. This is available by default on the Cisco router.

ii) Land Attack

A python file, landattack.py is created on the Ubuntu system and the code in Figure 5.8 is

populated into the file.

Figure 5.8: Python Code for LAND Attack

The code imports Scapy into the python file creating an IP object of type IP() for the

purpose of creating an IP header. With the target and source IP addresses being the destination IP

address, a TCP object of type TCP() is created, followed by mapping the destination port in the

TCP header as port 80 and the source port as 1000 (any random port number can be used). The 9th

line sets the SYN bit in the TCP header followed sending the IP packet with the TCP header. Since

the code is saved in a file with python extension, the execution is done as follows.

sudo python LANDATTACK.py

The execution of the python file is performed after the Wireshark is powered up in the

target machine to notice the received packets.

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 Figure 5.9 shows the packet, which was generated using the code. It clearly indicates that

the source and destination IP addresses in the IP header are the same as the target’s own IP address.

Also, TCP header is on destination port 80.

Figure 5.9: Wireshark Analysis of LAND Attack

Defense

Packets that have the source and destination IP addresses same as the value of the

destination IP address indicate a land attack. For defending against an attack, an ACL can be

configured on the router, which would deny packets with source and destination as the target’s IP

address. The below configuration shows how ACL can be used on a Cisco router to defend against

a land attack on the Windows XP system.

R2 (Configuration)

R2(config)#access-list 300 deny IP host 192.168.2.2 host 192.168.2.2

R2(config)#access-list 300 permit IP any any
R2(config)#interface serial 0/0
R2(config-if)#IP access-group 300 in

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 Verification

The code for land attack is generated after the ACL is set and configured. It can be observed

that the packet does not reach the server. The below screenshot shows the message from the router

(10.0.0.2) to the host 192.168.2.2 stating that the packet has been administratively filtered. This

can be observed on the Wireshark setup on Windows XP; Figure 5.10 indicates the same.

Figure 5.10: Filtered Packet during Defense

iii) IP Spoofing Attack

A python file, ipspoof.py is created on the Ubuntu system, and the code in Figure 5.11 is

populated into the file.

The code imports Scapy into the python file creating an IP object of type IP () for the

purpose of creating an IP header. The destination IP address is fed as input from the user and then

mapped to the IP header.

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 Figure 5.11: Python Code for IP Spoofing Attack

The source IP address in the IP header is the spoofed IP address, which is 172.16.0.1, with

the object of type ICMP(). The value of the ICMP header is set to 0 and the type value in the ICMP

header as 8. Since the code is saved in a file with python extension, the execution follows.

sudo python IPspoof.py

Figure 5.12 shows the source IP address in the IP packet is spoofed with the IP address

172.16.0.1, when received on the destination, which is Windows XP.

Figure 5.12: Wireshark Analysis of IP Spoofing Attack

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 Defense

An access control list is configured on the R2 router, which would block packets

originating from the source, 172.16.0.1, on the serial interface of the router. The details of the

configuration are provided below.

R2 (Configuration)

R2(config)#access-list 10 deny 172.16.0.1

R2(config)#access-list 10 permit any
R2(config)#interface serial 0/0
R2(config-if)#IP access-group 10 in

Verification

The code for IP Spoofing attack is generated after the ACL is setup and configured. The

packet does not reach the server.

Typically in a real time environment, ACLs are used to mitigate IP Spoofing attacks.

Border routers are configured to block IP packets originating from the Internet with private IP

addresses as source. The block of IP addresses is available in RFC 1918.

5.2.2 Layer 2 Assessment

We next modified the network as follows, shift the Ubuntu system to the network on which

the IIS server is configured. Configure the IP address of the system with the IP address,

192.168.2.3. Install nmap on the system.This assessment is completely in reference to the topology

indicated in Figure 5.3.

IP and Port Scanning: PC3 is configured with the IP address, 192.168.2.3. To identify the

IP addresses for the devices configured on the network and corresponding applications that are

residing on the respective systems, nmap tool is used. The tool is set and configured on PC3. The

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command nmap –PR 192.168.2.0/24, which is also known as the ARP ping scan, is used for the

purpose. The command execution gives the output, as shown in Figure 5.13.

Figure 5.13: Nmap Scan Indicating the Active Hosts

The scan has identified the IP addresses of the systems, which are currently on the network,

which are 192.168.2.1, 192.168.2.2 and 192.168.2.3, along with the respective mac-addresses and

port numbers. The port number, TCP port 80 on the system, 192.168.2.2, provides information

that a web server is set up and installed on it.

i) Cam Flooding Attack

A python file, camflood.py is created on the Ubuntu system and the code in Figure 5.14 is

populated into the file. The code generates a cam flooding attack by sending an ARP request packet

with random mac-addresses in a loop. Ubuntu system is connected to port ‘4’ on the switch in the

test.

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 Figure 5.14: Python Code for Cam Flooding Attack

The code imports the Scapy module, creates an Ethernet object of type Ethernet and then

maps the source mac-address of the Ethernet header as Random mac-addresses. This is used every

time a packet is sent as the source mac-address is to be changed for generating a cam flood attack.

This creates the destination mac-address in the Ethernet header as broadcast ram mac for the ARP

request packet. Further, this maps the destination IP address in the ARP header as the IP address

of the router and then sends a packet in a loop, which would send ARP request packets to the

router. Since the code is saved in a file with python extension, the execution is done as follows.

Figure 5.15 indicates the outcome.

sudo python camflood.py

Figure 5.15: Wireshark Analysis of Cam Flooding

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 After the code is executed, the following command on the console of the switch generates

an output as in Figure 5.16.

Switch#show mac-address-table

Figure 5.16: Cam Flooding on the Switch Console

Figure 5.16 shows that port 0/4, on which the code is executed, is filled up with random

mac-addresses, as in a cam flood attack.

Defense

In a cam flood attack, the goal of the attacker is to fill up the with mac-address table of the

switch with random mac-addresses. To prevent an attack, the port-security feature, which is

available on the switch can be used. The port-security feature would be configured to limit the

allowed mac-addresses on a switch port as 1. As only one PC would be connected to a switch port

in a typical scenario, only one mac-address is required. This would prevent an attacker to send

numerous mac-addresses through one port. The configuration is shown below.

Switch(config)# interface fastEthernet 0/4

Switch(config-if)#switchport mode access
Switch(config-if)#switchport port-security
Switch(config-if)#switchport port-security maximum 1
Switch(config-if)#switchport port-security violation restrict.

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 Verification

To verify, the command clear mac-address-table dynamic on the switch port will result in

violation and restriction for the numerous mac addresses on the switch port.

ii) Mac Spoofing Attack.

A python file, macspoofer.py is created on the Ubuntu system and the code in Figure 5.17

is populated into the file.

Figure 5.17: Mac Spoofing Code

The code upon execution, an ARP packet with a spoofed source address is sent to target switch.

Since the code is saved in a file with python extension, the execution follows. Figure 5.18 indicates

the outcome.

sudo python macspoofer.py

Figure 5.18: Wireshark Analysis for Mac Spoofing

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 It can be observed that, the source mac-address in the Ethernet header is a spoofed mac-

address (00:1b:78: ab: 9f:90).

Defense

The mac spoofing attack aims to send packets with spoofed mac-addresses. For prevention,

the port-security feature, which is available on the switch, can be used. The port-security feature

would be configured with the value of the allowed mac-address. This would typically be the mac-

address of the PC, which is connected to a specific port number. The existing configuration on

port 4 of the switch is removed before the configuration is performed.

Switch(config)# interface fastEthernet 0/4

Switch(config-if)#switchport mode access
Switch(config-if)#switchport port-security
Switch(config-if)#switchport port-security 00e0.1c3c.22b4
Switch(config-if)#switchport port-security violation shutdown.

Verification

For verification, open the switch console, and the following messages would be displayed

on the switch port. Also, it can be observed that the port progresses to shutdown state after the

spoofed mac-address is received on a specific port. Figure 5.19 indicates the same.

Figure 5.19: Indicating Security Violation

iii) STP Attack

A python file is created using the command via stpcrafter.py on the Ubuntu system and the

code in Figure 5.20 is populated into the file.

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 Figure 5.20: STP Attack Python Code

The code generates STP packets. The 4th line configures the destination mac-address of the

Ethernet frame with the multicast address for spanning tree protocol, which is 01:80: C2:00:00:00.

An object is created of type llc, as spanning tree protocols require an LLC header. Also creates an

object of type STP for creating the STP BPDU packet. A prototype is configured as type 0, for

IEEE 802.1d. STP version, bpduflags, rootid, rootmac, pathcost, bridgeid, bridgemac and portid

are all specified. Since the code is saved in a file with python extension, the execution follows.

Figure 5.21 displays the outcome.

sudo python stpcrafter.py

Figure 5.21: Wireshark Analysis of STP Attack

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 Defense

In an STP based attack, the goal of the attacker is to send BPDU packets with lower priority

value. The default priority value of Cisco switches is 32768. The STP BPDU guard provides

protection against an attack, by shutting down the ports, when an STP BPDU packet is received

on the port.

Switch(config)# interface fastEthernet 0/5

Switch(config-if)#spanning-tree bpdu-guard enable.

Verification

During the attack, if attempted after the configuration is performed, the port shuts down on

the receipt of the STP packet. This is observed on the switch console as shown in Figure 5.22.

Figure 5.22: Switch Port Verification

Apart from these attacks explained above, we have also conducted tests to examine other

possible attacks such as ARP cache poisoning, Smurf attacks and ping of death attack. The Scapy

scripts for these attacks are also generated and tested from the attacking Ubuntu machine.

Furthermore, MITM (Man in the Middle) and overlapping fragment attacks have also been

executed with successful outcomes. Thus, most of the possible modern attacks in the layer 2 and

layer 3 of TCP/IP model have been studied for network penetration testing.

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5.3 Application Penetration Testing

With the aim to design a lap to develop penetration testing mechanism concepts in a real

time environment, the details of the stages involved in the concept with the experiments conducted

are explained. We demonstrate a procedure to perform penetration testing in a complex topology

as a real time internet domain.

Functioning of a couple of applications on the attacker Linux machine are listed below;

these are helpful to evaluate the network scan and the port scan.

Dradis: Linux machine by default has this application. To start this service you need to

keep the terminal from the application>> start Dradis open. This runs on port 3004. To access

Dradis framework, the browser needs to be populated with https://localhost:3004.

Nessus: This is manually installed in Linux machine, and this runs on port number 8834.

To start this service, “service nessusd start” command is used. The following link needs to be used

https://localhost:8834, to navigate to Nessus.

5.3.1 Planning and Preparation

As discussed earlier, this is the phase where the pentester prepares a platform for

performing penetration. This makes it trivial for our experimentation as we built the topology and

the lab. So a proper listing of the target systems and the scope are prepared.

5.3.2 Information Gathering and Analysis

As this phase of the procedure deals with gathering information about the victim, the

essentials like IP address, server platform, and operating system are the focus. By definition of

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penetration testing, gathering information can be classified into active or passive based on the type

of interaction with the target system.

Ways of gathering information in a passive manner include researching about the network

by the name or website. For example, www.netcraft.com is a website that displays a network

information including IP addresses, server software information and domain name, owner, etc.

This also includes the history of the network, etc. There are a lot of other websites like DNS stuff,

domain tools to lookup the DNS, server location and so on.

Another important methodology of gathering information is through tracing the IP address

of the server. In an internal network, a regular ping through the terminal would resolve the network

IP address. “Nslookup” on the command line also resolves the IP address by host name. Using

socket programming also helps in this process. A series of code steps will resolve the host server’s

IP address from the hostname. The following is the code that can be used for gathering IP address

information.

Socket programming: Python code

import socket
import sys
try:
s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
except socket.error, msg:
sys.exit();
host = 'host_name'
try:
remote_ip = socket.gethostbyname( host )
sys.exit()
print 'IP address = ' + remote_ip

When it comes to actively gathering information, Netcat and telnet are few good tools in

the Linux terminal to gather information about the type of server. Also, metaspolit can be used to

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scan out the mssql, ftp version, etc. Figure 5.23 shows the usage of telnet to scan for the type of

server and its version. We used HEAD and HTTP combinations to communicate with server.

Figure 5.23: Telnet on the Victim

As you can see, the command telnet followed by the HTTP specification requests the server

for an HTTP response with the document headers. And in response the target machine provides a

list of header information including the server type, version and the source. In our case, the target

machine is powered by ASP.Net and is running Microsoft IIS 5.1. This information helps to

conclude on the type of platform and to further plan the procedure.

5.3.3 Vulnerability Detection

Once adequate information is acquired, scanning is followed. This is where the network is

scanned for all the host machines under the network and then are scanned for vulnerable ports

through port scan. In our case, Network scan with the DNS server is performed after obtaining the

IP address.

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 As discussed earlier, Nmap is a very handy tool on Linux machines to scan the network

and its ports. Ping sweep is a procedure that reveals the information of the host machines including

the servers’ state. The following is the syntax used to perform a ping sweep.

nmap –sP –v 192.82.46.1-3

 P-ping

 V-verbose

Figure 5.24 shows the execution outcome of the command. This command will send a ping

to all the hosts on the network and list the status of the host computers without performing the

three way handshaking. It also displays information regarding the host machine’s mac address.

This information regarding the type of operating system and the status of the host machines comes

in very handy in attacking the system.

Figure 5.24: Network Scanning via Ping Sweep

Now that the status of the host machines is analyzed, the information has to be stored in a

file format. This can be done using the following syntax that scans and saves data in .xsl file format.

nmap –A –oA nmap-scan –stylesheet=nmap.xsl 192.82.46.1-3

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 -A: enable OS detection, version

-oA: output in major formats

--stylesheet XSL style sheet

With the above command nmap corresponds to the result shown in Figure 5.25.

(a) Port Scan

(b) Trace Route

Figure 5.25: Scanning Using Nmap.

Subfigure (a) is port scan. Subfigure (b) is trace route. Subfigure (c) is browser view.

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(Figure 5.25 Continued)

(c) Browser View

Also, command executes to an output file obtained by the stylesheet, which individually

lists all the hosts with the port numbers, services and versions including smb details. Also, it clearly

shows the trace route to the target. To evaluate the level of vulnerability of each of these ports and

the ease of penetrating, Nessus and Dradis are used for vulnerability detection.

The 445 TCP port is the most critical port; we can back breach into the host through this

kind of port. The following nmap command is executed to check the vulnerability of this particular

port.

Nmap --script smb-check-vulns.nse --script-args=unsafe=1 192.82.46.3

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 As you can see in Figure 5.26, host script results in the TCP scans indicating that MS08-

067 and SMBv2 Dos are vulnerable on Windows XP and Windows 2008 server, respectively. The

file accessed in Nessus tool would display the critical ports and secure ports as below based on the

coloring as shown in Figure 5.27. Further a click on these tabs would navigate to more detailed

write up of the ports.

Figure 5.26: Vulnerability Scan Using Nmap

Figure 5.27: Dradis and Nessus Results for .Xml file

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 These Nessus and Dradis screenshots visualize comparison of the open ports of the

machine with a lucid description of the level of vulnerability as in critical, high and medium. This

vulnerabilities detection helps the pentester list down the various scripts for exploiting these

vulnerability to gain a back door access to the host machine.

5.3.4 Penetration Attempt

Once the scanning is accomplished, efforts to breach the network are followed. Here we

introduce the msfconsole, a new console designed by metaspolit to gain access to the host machines

through the vulnerable ports. Now that we have the information regarding mssql running on the

host, 192.82.46.2, Metasploit can be used to search and exploit the vulnerabilities. For this purpose,

a console designed in Metasploit is started from the services in the attacking machine. A simple

command “msfconsole” would then run the application.

Different operating systems expose different vulnerabilities. Some are well known

vulnerabilities, and many others are discovered every day in many applications. A list of the

various operating systems and their corresponding vulnerabilities that we have worked are as

follows

Windows xp - ms08_067_netapi

Windows 2003 server - ms08_067_netapi

Windows 2008 server - smb client, ms09_052

Windows 7 - smb client

Metasploitable - http, src, ftp, samba

OSX - iSight

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 All of these exploits with a respective payload help gain access to the target machines with

administrative controls. Once a session is successfully opened in the target machine, maintaining

access and further exploitation is different from one OS to another.

As mentioned earlier, scanning, exploiting and post exploiting actions can be performed

using metaspolit. Initially for the confirmation of the existence of mssql, the “search mssql”

command results in a list of the attributes that can be used. From the list, the following command

opens the console for mssql_ping.

Use auxiliary/scanner/mssql/mssql_ping

“Show options” in this console lists options needed to gather information of the server

running. Once the required details are populated with the available information, the details shown

in Figure 5.28 can be obtained.

Figure 5.28: Auxiliary scan using Metasploit for Mssql

Once the requirements are populated with the necessary details of the RHOSTS and

THREADS, the console would indicate the version and the name of the server the network is

running.

Hydra and medusa could be used to crack the password for the server. Hydra uses a

dictionary attack from the FastTrack’s wordlist.

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 Hydra –l sa –p /usr/share/set/src/fasttrack/wordlist.txt mssql://10.10.10.3

-l login

-p password

This is going to display the password of the mssql password for username ‘sa’ as shown in

Figure 5.29.

Figure 5.29: Password Cracking Using Hydra

With the cracked password and the mssql details, we now use the login module to try and

login to the mssql server on the host machine, as shown in Figure 5.30.

Use auxiliary/scanner/mssql/mssql_login

Figure 5.30: Logging Into the Target Machine

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 Now, using the login auxiliary of mssql and populating the required options would login

into the mssql on the host machine. Now mssql_exec module would let us access to the machine.

Similar to the previous steps, do the following,

Use admin/mssql/mssql_exec

When executed, this command lets the pentester add a user to the host machine with the

Windows command prompt commands.

Meterpreter is dynamic Metasploit payload that is extended over the runtime to exploit.

Mssql_payload is used in exploiting to perform the exploitation into the machine. In the packages

and scripts that are involved in Metasploit, a number of payloads are listed. Use this payload as

follows,

Set PAYLOAD windows/meterpreter/reverse- TCP

Again populating the required attributes in the options, a meterpreter session is successfully

accomplished. This accomplishment explains that the exploitation is successful. For verification,

shell as shown in Figure 5.31, opens a command prompt console of the Windows machine.

Figure 5.31: Exploit and Payload Results

This session determines the connection to the machine of the mssql holder.

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 Now the other vulnerability that we worked on is smb, netapi to exploit the Windows 2003

server machine. For this search for netapi on msfconsole use

exploit/windows/smb/ms08_067_netapi

And further with the options, it will check the host for the vulnerability. Here with the use

of the similar payload as that of the previous operation, Figure 5.32 is obtained. Subfigures (a) and

(b) show meterpreter for the Windows server 2003 machine and the shell respectively. From here,

migration into other services and file transfer is just as the operations performed on windows.

(a) Meterpreter session

(b) Shell

Figure 5.32: Windows Server 2003 Exploitation.

Subfigure (a) is meterpreter session. Subfigure (b) is shell of victim.

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 Hashdump is used to crack the passwords from the server machine. “Hashdump” is an

inbuilt service in the meterpreter and runs by just typing Hashdump. This service will copy all the

hashes from the target machine. This file is extracted using John the Ripper, which is a ripper to

decode hashdumps. A command in the format below will crack the file to display login hashes.

(c) John --format=nt2 (file location)

Finally, Metasploitable is running mysql from the report of the port scan. Similar procedure

as Windows xp, msfconsole would breach into the Metasploitable system too.

Mysql –h 10.10.10.4 –u guest –p

This command will login to the mysql and further will list databases as in Figure 5.33.

Figure 5.33: Results for Metasploitable Exploit

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 Further using the attributes in the list, access to all the information in the Metasploitable

are available.

Maintain: This phase also deals with maintaining the gained access. For this purpose,

creating a hidden user and hiding the account from the registry will ease the procedure. From

here on login into the server with the hidden user and password, the remote desktop is enabled

on the attacking machine as shown in Figure 5.34.

rdesktop –u username –p password –d domain-name 10.10.10.2

Figure 5.34: Remote Desktop Connection to the Target.

Logging into the target machine ends the basic procedure of penetration testing. A similar

procedure on the operating systems like Windows 2008 server and Windows 7 were also

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performed targeting different vulnerabilities. Exploits in 2008 server and Windows 7 also include

the following,

smb/ms09_050_smb2_negotiate_func_index

smb/ms10_006_negotiate_response_loop

These exploits have also been exploited and tested for successful attacks. Now that the

exploitation is successful, through the server, we can login to the host machines, create users,

administrators and also manage to hide from the notification center. With this kind of access to the

machine, anything is possible.

5.3.5 Analysis and Reporting

As a penetration tester, with all the experimentation procedure and results, detailed

documentation needs to be prepared for the official customer reasons. This document must also

include the mitigation techniques. Few of the most useful mitigations for intruder attacks of this

kind include the following.

 Disable all redundant services

 Timely updates on Operating sytems
 Firewall turned ON
 Credible Anti-virus
 Configure IDS/IPS at server side and having a strong DMZ

5.3.6 Cleaning Up

This phase of the penetration testing is to set back everything to its usual running conditions

to make things functional as before. In simple words, it is just undoing all the above phases. Things

like creating users, modifying files and applications, changing router configurations have to be

71
concentrated as this might lead to back drop of the functionality of an organization. Furthermore,

removing cache files and temporary files is most important as these leave traces of work. Also, let

the malicious user, if any, inside the network to gather information.

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 6. CONCLUSION AND FUTURE WORK

This chapter concludes the research with appropriate research contributions, problem

statements and aspiring future works.

This work emphasizes the importance of penetration testing in building a much more

challenging network. Furthermore, this thesis demonstrates the working of BGP in a physical

laboratory environment and employs the usage of different tools for penetration testing. We have

presented the various vulnerabilities that are commonly notified in any network. Also, we have

demonstrated a laboratory setup that replicates an organizational network.

These contributions would help enthusiasts to utilize and enhance methodologies to

discover more vulnerabilities in the scale of router and desktop integration.

The following are the crucial problem statements that are performed during the research,

 Penetration testing types, phases and applications

 Border Gateway Protocol implementation in a lab

 Vulnerabilities in the network equipment

 Vulnerabilities in different applications on host machines

This thesis elaborates a process of performing penetration tests on a real network.

Irrespective of the operating system and the usability, the vulnerabilities are tracked down using

various tools and applications. A detailed introduction to various penetration testing, BGP, testing

tools and frameworks is accompanied by its analysis in a laboratory environment. This thesis

supported the utility and the feasibility of the penetration testing methodology in different phases.

The prototype of an organizational network is demonstrated in the lab implementing the current

main internet domain protocol (BGP). In conclusion, penetration testing is the highest level of

73
assessment for any network as this examines elaborated vulnerabilities in a physical network

contributing in mitigation. Though the manufacturers of the network equipment and the servers

strive to mitigate the existing vulnerabilities, there are always new threats emerging. As the

advancements in the sophisticated technology are inevitable, so are the vulnerabilities. Successful

penetration tests with a proper methodology on a regular basis guarantee the security of any

organization fetching customer trust.

With this thesis as base, most appropriate future work would be attacking vulnerabilities

in BGP protocol to intercept traffic via sending malicious packets amongst trusted peers inside the

network. Developing Metasploit scripts with a novel aim to run successful exploits against the

defended bugs in various Windows environments using ruby language will be a good idea. Also,

fuzzer coding is fascinating to learn and design which helps sending forged packets to various

vulnerable applications. Most importantly, automating the process of penetration testing as any

other software application will help organizations to confidently secure their network with required

minimal knowledge. Furthermore, Social engineering is usually overlooked creating an unknown

back door. Logical methods in emphasizing the confidentiality during social gatherings and

websites will help restrict the information gathering by an attacker.

74
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 APPENDICES

Appendix 1: Laboratory Configurations

Table A1.1: PC Configurations

IP address: 192.82.46.2/24

PC0 (Linux) Gateway: 192.82.46.1

IP address: 192.82.46.3/24

PC1 (Ubuntu) Gateway: 192.82.46.1

IP address: 192.168.4.3/24

PC3 (Windows Server 2003) Gateway: 192.168.4.1

IP address: 192.168.4.4/24

PC4 Gateway: 192.168.4.1

Table A1.2: Router Configurations

Fast Ethernet 0/0 : 192.82.46.1

Router0 (AS 200) Serial 0/0/0 : 200.200.200.5 Serial 0/1/0 : 200.200.200.2

Fast Ethernet 0/0 :192.168.1.1

Router1 (AS 100) Serial 0/0/0 :200.200.200.1 Serial 0/1/0 :200.200.200.10

Fast Ethernet 0/0 :192.12.16.1

Router2 (AS 300) Serial 0/0/0 :200.200.200.6 Serial 0/1/0 :200.200.200.13

Fast Ethernet 0/0 :192.168.4.1

Router3 (AS 100) Serial 0/0/0 :200.200.200.9

Fast Ethernet 0/0 :192.12.20.1

Router4 (AS 300) Serial 0/0/0 :200.200.200.14

79
Appendix 2: Topology and Outputs of Cisco Tools

Figure A2.1: Topology Used to Configure the ASA on GNS3

Figure A2.2: Communication between the LAN and DMZ

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 (a) Router Side

Figure A2.3: Security Levels to the LAN, DMZ and WAN Areas in the Network. Subfigure (a)

Router side. Subfigure (b) Firewall side.

(b) Firewall side

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 (a) Topology 1

Figure A2.4: Topologies Used in CPT to Implement the CCNA Security. Subfigure (a) is

the topology 1. Subfigure (b) is the topology 2.

(b) Topology 2

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Appendix 3: Supportive Screenshots for Pentesting

Figure A3.1: Successful Exploit to Windows 2008 Server

Figure A3.2: Resolving IP Address with DNS Lookup

83
Figure A3.3: BGP Peers and IP Route

84
Appendix 4: Tools and Frameworks

i) Tabulated description of various tools used for this research

Table A4.1: Tools Description

No Tools References Description

1. Brutus [10] This is a password cracker to crack passwords that are

hashed. It is the most flexible remote password
cracker including authentication types like POP3,
FTP, SMB, telnet etc.
2. Dradis [48] This is an open source framework to enable effective
information sharing. Dradis framework would
hold documentation of the scan reports and have
a notes against the ports and vulnerabilities in a
user account. It automatically categorizes data
into various standard fields letting the user have a
procedural execution of a particular task over a
port or an application.
3. DNSstuff [11] This website creates a complete DNS report of any
website that a user puts in. It provides information
of the www tools, IP tools, networking tools and
email tools involving Mail, DN Sec, SPF, SOA
details of the well-established websites. It also
understands various other features like examining
SSL, DNS lookup, TLD lookup, ISP cached DNS
lookup etc. Further it is enhanced with the inbuilt
feature of Whois lookup.
4. Hydra [49] A password cracker, but efficiently quicker and
cracks password based on the dictionary and brute
force attacks. Hydra is a paralyzed login cracker
which supports numerous protocols to attack.
This helps crack down the weak passwords on a
network.
5. John the [17] This is a password cracker works best with the UNIX
Ripper machines to detect weak passwords. Also features
crypt (3) password hash types. It is a widely
available open source password cracking tool. It
is distributed primarily in source code form, and
can be compiled with several different options.

85
(Table A4.1 Continued)
No Tools References Description

6. Hping [13] [14] This is a network security tool mostly used to send
files between various protocols like TCP, UDP,
and ICMP. Hping allows its users to craft variable
packets like IPv4/TCP/UDP/ICMP packets with
specifications of the details of contents in those
protocol headers. This also includes a number of
other applications in network security as follows:
Firewall testing, Advanced port scanning,
Network testing, Manual path MTU discovery,
Advanced trace route, Remote OS fingerprinting,
Remote uptime guessing, TCP/IP stacks auditing.
It is a command-line oriented TCP/IP packet
assembler/analyzer. It works in almost all the
Linux and UNIX based platforms.
7. Kali Linux [1] Kali Linux is an offensive security operating system
replacing Back Track Linux. This is debian
derived tool kit with advanced features that
involve and enable better penetration testing
abilities. It is the same creators as of the
Backtrack. It is the most sophisticated tool to
perform penetration testing distribution. It is also
the most stable and adaptive environment for the
purpose ever created.
8. Metasploitable [50] This is a vulnerable target machine designed by the
developers of the Metasploit for learning,
exploring and understanding purposes. It is
comprised of vulnerable ports, applications, web
services, weak passwords and backdoors.
9. Nmap [7] It is used in a variety of applications by users to
ensure the quality, type, services of any particular
network. Gordon Lyon, Nmap suite includes an
advanced GUI and results viewer (Zenmap), a
flexible data transfer, redirection, and debugging
tool (Ncat), scan results (Ndiff), and a packet
generation (Nping). For operating system,
application and services.

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(Table A4.1 Continued)
No Tools References Description

10. Metasploit [2][3][4] This is a penetration testing software used by the

penetration testers to efficiently perform tasks
like discovery, exploitation, brute forcing and
reporting. It’s an exploitation framework. It is
group of utilizes and tool put together to establish
an exploit for penetration testing. It helps develop
fuzzer codes to design an exploit. With scripting
it lets the users to design their own exploit with
the packages and utilizes inbuilt in the
framework. It also involves tools like Meterpreter
and PS Exec that which enable users to script and
hash the passwords on a computer with known
credentials. Metaspolit is a complete package
involving 613 exploits, 306 auxiliary modules,
215 payloads, and 20 encoders. With the
combination these exploits, payloads, scripts and
modules, amazing features like a vulnerability
scanner, port scanner, meterpreter execution,
backdoor installation, VNC injection, FTP, SMB
and HTTP client, and remote shell execution.
Meterpreter is considered the most powerful
payload in the study of penetration testing right
from the Backtrack. Its main use is to provide
complex and advanced features that would
otherwise be tedious to implement in assembly
[5]. It displays highly enhanced and integrated
payload structure that runs using DLL stagers.
During exploitation meterpreter has ability to
create a client side PowerShell that could be used
to manipulate the system information with the
command prompt commands on the client side.
The three applications of the console in
Metasploit include auxiliary, exploit and post
used for scanning, exploiting and post exploiting
respectively.

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(Table A4.1 Continued)
No Tools References Description

11. Maltego [51] This is developed to deliver a clear threat picture to

the environment that an organization owns and
operates. It clearly visualizes the complexity in
any network infrastructure pictorially.

12. Netcraft [8] This is a very popular website, owned by the netcraft
that provides a variety of internet services which
include anti-fraud and anti-phishing services,
application testing, PCI scanning, market share of
web servers, operating systems, hosting providers
and SSL certificate authorities. Like, Domain,
DNS admin name, IP address, hosting nation,
hosting history, security level, operating system
of the server, server application, the site
technology, scripts involved in the database,
document type etc. Netcraft also communicates
the sites database and displays information
regarding the blacklisted websites.

13. Nessus [15] [16] Nessus is a vulnerability scanner that ensures network
security by identifying vulnerabilities and further
reducing risk. It has tight integration with
malware defenses, patch management tools,
BYOD, firewalls, cloud infrastructure and
virtualized systems. Nmap scan report exported to
Nessus for better visualization and understanding
provides a keen report. Vulnerability scanning
service that may be used to audit Internet-facing
IP addresses for both network and web
application vulnerabilities “from the cloud”. This
website is well organized with the scans, reports,
policies and users.

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(Table A4.1 Continued)
No Tools References Description

14. Netcat [12] Netcat is a featured networking utility which reads

and writes data across network connections, using
the TCP/IP protocol. It is a tool that provides a
connection to the TCP and UDP along with
tunneling mode to help tunneling between TCP
and UDP. Also, buffered send-mode, hex dump,
and port-scanning and telnet codes. Additional
features involve optional RFC854 telnet codes,
buffered send mode and hexdump of the data.
15. Python [52] It is a programming language, which is used with
Scapy. Python 2.7.3 is used for the purpose to
develop codes for attacks.

16. Scapy [53] It is a packet crafting framework, which is used for

demonstrating IP Spoofing, Land attacks, mac-
spoofing, cam-flooding and STP based attacks.
Scapy 2.2.0 is used for the purpose.

17. Ubuntu [6] It is a Linux based operating system optimized for

desktop usage, with previous version being
GNOME. This is one of the free ware of the Linux
operating systems that comes very handy with the
python implementation along with Hping helping
penetration testing.
18. Wireshark [54] This tool is a packet analyzer, which is used for
analyzing the attacks generated and verifying
their anatomy on the target. Wireshark version
1.8.2 is used for the purpose.

89
ii) Tabulated Description of Various Frameworks Studied Used for this Research
Table A4.2: Frameworks Description

No Framework Reference Description

1. WASC [34] Web Application Security

Consortium
2. OSSTMM [34] Open Source Security Testing
Methodology Manual
3. OWASP top 10 [34] Open Web Application Security
Project
4. ISSAF [34] Information Systems Security
Assessment Framework
5. NIST [34] National Institute of Standards and
Technology

90
 VITA

Bharath Kumar Koopari Roopkumar, a native of Hyderabad, India, was born on 14 August

1990 to Mrs. Koopari Padma and Mr. Koopari Roopkumar. After finishing his schooling from

Siddhartha Convent High School in 2005, he graduated 12th from Prathibha Junior College,

Hyderabad. He studied Electronics and Communication Engineering at Jawaharlal Nehru

Technological University in Hyderabad, India, from 2008 through 2012 toward obtaining his

Bachelor of Technology. Immediately after graduating, he got approved for admission at Louisiana

State University, Baton Rouge for fall 2012. Since then, he is pursuing his Master’s program as a

graduate student in Electrical Engineering Department. During his time at LSU, he has been

working as a Graduate Assistant for Humanities and Social Sciences Department. He will receive

his master’s degree in December 2014 and plans to begin MBA the following semester.

91