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Gray Hat Hacking, Third Edition Reviews
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from the start. Always right on time information, always written by experts. The Third
Edition is a must-have update for new and continuing security experts.”
                                                                          —Jared D. DeMott
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and broaden their skills in a wide range of IT security disciplines.”
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                                                                                     Hacker
“The Third Edition of Gray Hat Hacking builds upon a well-established foundation to
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From software exploitation to SCADA attacks, this book covers it all. Gray Hat Hacking
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        Gray Hat
        Hacking
       The Ethical Hacker’s
          Handbook   Third Edition
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To my brothers and sisters in Christ, keep running the race. Let your light shine for Him,
                          that others may be drawn to Him through you. —Allen Harper
To Jessica, the most amazing and beautiful person I know. —Jonathan Ness
For my train-loving son Aaron, you bring us constant joy! —Chris Eagle
              To Vincent Freeman, although I did not know you long, life has blessed us
                        with a few minutes to talk and laugh together. —Terron Williams
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      ABOUT THE AUTHORS
Allen Harper, CISSP, PCI QSA, is the president and owner of N2NetSecurity, Inc. in
North Carolina. He retired from the Marine Corps after 20 years and a tour in Iraq.
Additionally, he has served as a security analyst for the U.S. Department of the Treasury,
Internal Revenue Service, and Computer Security Incident Response Center (IRS CSIRC).
He regularly speaks and teaches at conferences such as Black Hat and Techno.
Shon Harris, CISSP, is the president of Logical Security, an author, educator, and secu-
rity consultant. She is a former engineer of the U.S. Air Force Information Warfare unit
and has published several books and articles on different disciplines within informa-
tion security. Shon was also recognized as one of the top 25 women in information
security by Information Security Magazine.
Chris Eagle is a senior lecturer in the Computer Science Department at the Naval Post-
graduate School (NPS) in Monterey, California. A computer engineer/scientist for
25 years, his research interests include computer network attack and defense, computer
forensics, and reverse/anti-reverse engineering. He can often be found teaching at Black
Hat or spending late nights working on capture the flag at Defcon.
Gideon Lenkey, CISSP, is the president and co-founder of Ra Security Systems, Inc., a
New Jersey–based managed services company, where he specializes in testing the infor-
mation security posture of enterprise IT infrastructures. He has provided advanced
training to the FBI and served as the president of the FBI’s InfraGard program in New
Jersey. He has been recognized on multiple occasions by FBI director Robert Muller for
his contributions and is frequently consulted by both foreign and domestic govern-
ment agencies. Gideon is a regular contributor to the Internet Evolution website and a
participant in the EastWest Institute’s Cybersecurity initiative.
Terron Williams, NSA IAM-IEM, CEH, CSSLP, works for Elster Electricity as a Senior Test
Engineer, with a primary focus on smart grid security. He formerly worked at Nortel as a
Security Test Engineer and VoIP System Integration Engineer. Terron has served on the
editorial board for Hakin9 IT Security Magazine and has authored articles for it. His inter-
ests are in VoIP, exploit research, SCADA security, and emerging smart grid technologies.
Disclaimer: The views expressed in this book are those of the authors and not of the
U.S. government or the Microsoft Corporation.
                               www.it-ebooks.info
About the Technical Editor
Michael Baucom is the Vice President of Research and Development at N2NetSecurity,
Inc., in North Carolina. He has been a software engineer for 15 years and has worked
on a wide variety of software, from router forwarding code in assembly to Windows
applications and services. In addition to writing software, he has worked as a security
consultant performing training, source code audits, and penetration tests.
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                          CONTENTS AT A GLANCE
viii
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                                                                                                                             Contents
                                                                                                                                   ix
  Part IV    Vulnerability Analysis                  . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 411
Chapter 20   Passive Analysis             ........................................                                     413
Chapter 21   Advanced Static Analysis with IDA Pro                         ......................                      445
Chapter 22   Advanced Reverse Engineering                       ............................                           471
Chapter 23   Client-Side Browser Exploits                   ..............................                             495
Chapter 24   Exploiting the Windows Access Control Model                                ...............                525
Chapter 25   Intelligent Fuzzing with Sulley                  .............................                            579
Chapter 26   From Vulnerability to Exploit                  ..............................                             595
Chapter 27   Closing the Holes: Mitigation                  ..............................                             617
Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 673
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                                                    CONTENTS
                Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xxiii
                Acknowledgments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xxv
                Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xxvii
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                                                                                                                                      xi
            Case Studies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .    67
                  Pros and Cons of Proper Disclosure Processes . . . . . . . . . . . . . .                                67
                  Vendors Paying More Attention . . . . . . . . . . . . . . . . . . . . . . . . . .                       71
            So What Should We Do from Here on Out? . . . . . . . . . . . . . . . . . . . . .                              72
                  iDefense and ZDI . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              72
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                                      Starting Network Services . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .           130
                               Persisting Changes to Your BackTrack Installation . . . . . . . . . . . . . . . .                        131
                                      Installing Full BackTrack to Hard Drive or USB Thumb Drive . . .                                  131
                                      Creating a New ISO with Your One-time Changes . . . . . . . . . . .                               134
                                      Using a Custom File that Automatically Saves and
                                         Restores Changes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .         135
                               Exploring the BackTrack Boot Menu . . . . . . . . . . . . . . . . . . . . . . . . . . .                  137
                               Updating BackTrack . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .       139
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                                                                                                                                      xiii
                    Sample Program . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              178
                    Compiling with gcc . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              179
             Computer Memory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              180
                    Random Access Memory (RAM) . . . . . . . . . . . . . . . . . . . . . . . . .                            180
                    Endian . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .      180
                    Segmentation of Memory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                    181
                    Programs in Memory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                  181
                    Buffers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .     182
                    Strings in Memory . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             182
                    Pointers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .      182
                    Putting the Pieces of Memory Together . . . . . . . . . . . . . . . . . . . .                           183
             Intel Processors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .       184
                    Registers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .     184
             Assembly Language Basics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                 184
                    Machine vs. Assembly vs. C . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                    185
                    AT&T vs. NASM . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             185
                    Addressing Modes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              188
                    Assembly File Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .               189
                    Assembling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .          189
             Debugging with gdb . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             190
                    gdb Basics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .        190
                    Disassembly with gdb . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                191
             Python Survival Skills . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .           192
                    Getting Python . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .            192
                    Hello World in Python . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                 193
                    Python Objects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .            193
                    Strings . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .     193
                    Numbers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .         195
                    Lists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .   196
                    Dictionaries . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .        197
                    Files with Python . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             197
                    Sockets with Python . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .               199
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xiv
                                       Determine the Attack Vector . . . . . . . . . . . . . . . . . . . . . . . . . . . . .            221
                                       Build the Exploit Sandwich . . . . . . . . . . . . . . . . . . . . . . . . . . . . .             222
                                       Test the Exploit . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .   222
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                                                                                                                           Contents
                                                                                                                                xv
             Implementing Reverse Connecting Shellcode . . . . . . . . . . . . . . . . . . . .                       284
                  Reverse Connecting C Program . . . . . . . . . . . . . . . . . . . . . . . . . .                   284
                  Reverse Connecting Assembly Program . . . . . . . . . . . . . . . . . . . .                        285
             Encoding Shellcode . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .    287
                  Simple XOR Encoding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              287
                  Structure of Encoded Shellcode . . . . . . . . . . . . . . . . . . . . . . . . . .                 288
                  JMP/CALL XOR Decoder Example . . . . . . . . . . . . . . . . . . . . . . . .                       288
                  FNSTENV XOR Example . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                289
                  Putting the Code Together . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              291
             Automating Shellcode Generation with Metasploit . . . . . . . . . . . . . . .                           294
                  Generating Shellcode with Metasploit . . . . . . . . . . . . . . . . . . . . .                     294
                  Encoding Shellcode with Metasploit . . . . . . . . . . . . . . . . . . . . . .                     295
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Gray Hat Hacking, The Ethical Hacker’s Handbook, Third Edition
xvi
                               Analyzing a Malicious PDF Exploit . . . . . . . . . . . . . . . . . . . . . . . . . . . .                     348
                                     Implementing Safeguards in Your Analysis Environment . . . . .                                          350
                               Tools to Detect Malicious PDF Files . . . . . . . . . . . . . . . . . . . . . . . . . . . .                   351
                                     PDFiD . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .       351
                                     pdf-parser.py . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .         355
                               Tools to Test Your Protections Against Content-type Attacks . . . . . . . .                                   358
                               How to Protect Your Environment from Content-type Attacks . . . . . .                                         359
                                     Apply All Security Updates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                  359
                                     Disable JavaScript in Adobe Reader . . . . . . . . . . . . . . . . . . . . . . .                        359
                                     Enable DEP for Microsoft Office Application and
                                         Adobe Reader . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .            360
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                                                                                                                                   Contents
                                                                                                                                       xvii
             SCADA Fuzzing . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .           399
                  SCADA Fuzzing with Autodafé . . . . . . . . . . . . . . . . . . . . . . . . . . .                          399
                  SCADA Fuzzing with TFTP Daemon Fuzzer . . . . . . . . . . . . . . . .                                      405
             Stuxnet Malware (The New Wave in Cyberterrorism) . . . . . . . . . . . . . .                                    408
             How to Protect Against SCADA Attacks . . . . . . . . . . . . . . . . . . . . . . . . .                          408
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xviii
                                        SPIKE Static Content Primitives . . . . . . . . . . . . . . . . . . . . . . . . . .                 489
                                        SPIKE Proxy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .     492
                                        Sharefuzz . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .   492
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                                                                                                                                    xix
             Analyzing Access Control for Elevation of Privilege . . . . . . . . . . . . . . .                            553
             Attack Patterns for Each Interesting Object Type . . . . . . . . . . . . . . . . . .                         554
                   Attacking Services . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .           554
                   Attacking Weak DACLs in the Windows Registry . . . . . . . . . . . .                                   560
                   Attacking Weak Directory DACLs . . . . . . . . . . . . . . . . . . . . . . . . .                       564
                   Attacking Weak File DACLs . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                    569
             What Other Object Types Are Out There? . . . . . . . . . . . . . . . . . . . . . . .                         573
                   Enumerating Shared Memory Sections . . . . . . . . . . . . . . . . . . . .                             573
                   Enumerating Named Pipes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                    574
                   Enumerating Processes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .                575
                   Enumerating Other Named Kernel Objects (Semaphores,
                      Mutexes, Events, Devices) . . . . . . . . . . . . . . . . . . . . . . . . . . . .                   576
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xx
                               Patching . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .   619
                                     Source Code Patching Considerations . . . . . . . . . . . . . . . . . . . . .                            620
                                     Binary Patching Considerations . . . . . . . . . . . . . . . . . . . . . . . . . .                       622
                                     Binary Mutation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .              626
                                     Third-Party Patching Initiatives . . . . . . . . . . . . . . . . . . . . . . . . . .                     631
Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 673
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                                        PREFACE
This book has been developed by and for security professionals who are dedicated to
working in an ethical and responsible manner to improve the overall security posture
of individuals, corporations, and nations.
xxi
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                                 ACKNOWLEDGMENTS
       Each of the authors would like to thank the editors at McGraw-Hill. In particular, we
       would like to thank Joya Anthony. You really kept us on track and helped us through
       the process. Your dedication to this project was truly noteworthy. Thanks.
           Allen Harper would like to thank his wonderful wife, Corann, and daughters,
       Haley and Madison, for their support and understanding through this third edition. It
       is wonderful to see our family grow stronger in Christ. I love you each dearly. In addi-
       tion, Allen would like to thank the members of his Church for their love and support.
       In particular, Rob Martin and Ronnie Jones have been true brothers in the Lord and
       great friends. Also, Allen would like to thank other hackers who provided assistance
       through the process: Alex Sotirov, Mark Dowd, Alexey Sintsov, Shuichiro Suzuki, Peter
       Van Eeckhoutte, Stéfan Le Berre, and Damien Cauquil.
           Shon Harris would like to thank the other authors and the team members for their
       continued dedication to this project and continual contributions to the industry as a
       whole. Shon would also like to thank the crazy Fairbairn sisters—Kathy Conlon, Diane
       Marshall, and Kristy Gorenz for their lifelong support of Shon and her efforts.
           Jonathan Ness would like to thank Jessica, his amazing wife, for tolerating the long
       hours required for him to write this book (and hold his job, and his second job, and
       third “job,” and all the side projects). Thanks also to Didier Stevens for the generous
       help with Chapter 16 (and for providing the free PDF analysis tools at http://blog
       .didierstevens.com/programs/pdf-tools). Big thanks also to Terry McCorkle for his
       expert guidance and advice, which led to the current Chapter 17—you’re a life-saver,
       Terry! Finally, Jonathan would like to thank the mentors, teachers, coworkers, pastors,
       family, and friends who have guided him along his way, contributing more to his suc-
       cess than they’ll ever know.
           Chris Eagle would like to acknowledge all of the core members of the DDTEK
       crew. The hard work they put in and the skills they bring to the table never cease to
       amaze him.
           Gideon Lenkey would like to thank his loving and supportive family and friends
       who patiently tolerate his eccentric pursuits. He’d also like to thank all of the special
       agents of the FBI, present and retired, who have kept boredom from his door!
           Terron Williams would like to thank his lovely wife, Mekka, and his stepson, Christian
       Morris. The two of you are the center of my life, and I appreciate each and every second
       that we share together. God is truly good all of the time. In addition, Terron would like
       to thank his mother, Christina Williams, and his sister, Sharon Williams-Scott. There is
       not a moment that goes by that I am not grateful for the love and the support that you
       have always shown to me.
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                                   INTRODUCTION
                                 I have seen enough of one war never to wish to see another.
                                                                      —Thomas Jefferson
      I know not with what weapons World War III will be fought, but World War IV will be
                                                             fought with sticks and stones.
                                                                       —Albert Einstein
    The art of war is simple enough. Find out where your enemy is. Get at him as soon as you
                                    can. Strike him as hard as you can, and keep moving on.
                                                                         —Ulysses S. Grant
    The goal of this book is to help produce more highly skilled security professionals
who are dedicated to protecting against malicious hacking activity. It has been proven
over and over again that it is important to understand one’s enemies, including their
tactics, skills, tools, and motivations. Corporations and nations have enemies that are
very dedicated and talented. We must work together to understand the enemies’ pro-
cesses and procedures to ensure that we can properly thwart their destructive and mali-
cious behavior.
    The authors of this book want to provide the readers with something we believe the
industry needs: a holistic review of ethical hacking that is responsible and truly ethical
in its intentions and material. This is why we are starting this book with a clear defini-
tion of what ethical hacking is and is not—something society is very confused about.
    We have updated the material from the first and second editions and have attempted
to deliver the most comprehensive and up-to-date assembly of techniques, procedures,
and material. Nine new chapters are presented and the other chapters have been
updated.
    In Part I of this book we lay down the groundwork of the necessary ethics and ex-
pectations of a gray hat hacker. This section:
     • Clears up the confusion about white, black, and gray hat definitions and
       characteristics
     • Reviews the slippery ethical issues that should be understood before carrying
       out any type of ethical hacking activities
     • Reviews vulnerability discovery reporting challenges and the models that can
       be used to deal with those challenges
     • Surveys legal issues surrounding hacking and many other types of malicious
       activities
     • Walks through proper vulnerability discovery processes and current models
       that provide direction
   In Part II, we introduce more advanced penetration methods and tools that no other
books cover today. Many existing books cover the same old tools and methods that have
xxiii
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xxiv
           been rehashed numerous times, but we have chosen to go deeper into the advanced mech-
           anisms that real gray hats use today. We discuss the following topics in this section:
                 • Automated penetration testing methods and advanced tools used to carry out
                   these activities
                 • The latest tools used for penetration testing
                 • Physical, social engineering, and insider attacks
               In Part III, we dive right into the underlying code and teach the reader how specific
           components of every operating system and application work, and how they can be ex-
           ploited. We cover the following topics in this section:
                 • Program Coding 101 to introduce you to the concepts you will need to
                   understand for the rest of the sections
                 • How to exploit stack operations and identify and write buffer overflows
                 • How to identify advanced Linux and Windows vulnerabilities and how they
                   are exploited
                 • How to create different types of shellcode to develop your own proof-of-
                   concept exploits and necessary software to test and identify vulnerabilities
                 • The latest types of attacks, including client-based, web server, VoIP, and
                   SCADA attacks
              In Part IV, we go even deeper, by examining the most advanced topics in ethical
           hacking that many security professionals today do not understand. In this section, we
           examine the following:
                 • Passive and active analysis tools and methods
                 • How to identify vulnerabilities in source code and binary files
                 • How to reverse-engineer software and disassemble the components
                 • Fuzzing and debugging techniques
                 • Mitigation steps of patching binary and source code
               In Part V, we have provided a section on malware analysis. At some time or another,
           the ethical hacker will come across a piece of malware and may need to perform basic
           analysis. In this section, you will learn about the following topics:
                 • Collection of your own malware specimen
                 • Analysis of malware, including a discussion of de-obfuscation techniques
               If you are ready to take the next step to advance and deepen your understanding of
           ethical hacking, this is the book for you.
               We’re interested in your thoughts and comments. Please send us an e-mail at
           [email protected]. Also, for additional technical information and re-
           sources related to this book and ethical hacking, browse to www.grayhathackingbook
           .com or www.mhprofessional.com/product.php?cat=112&isbn=0071742557.
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                               PART I
       Introduction to Ethical
             Disclosure
■   Chapter 1   Ethics of Ethical Hacking
■   Chapter 2   Ethical Hacking and the Legal System
■   Chapter 3   Proper and Ethical Disclosure
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  Ethics of Ethical Hacking
                                                                               CHAPTER
                                                                                                1
This book has not been compiled and written to be used as a tool by individuals who
wish to carry out malicious and destructive activities. It is a tool for people who are
interested in extending or perfecting their skills to defend against such attacks and dam-
aging acts. In this chapter, we’ll discuss the following topics:
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4
               Most countries’ militaries carry out various scenario-based fighting exercises. For ex-
           ample, pilot units split up into the “good guys” and the “bad guys.” The bad guys use the
           same tactics, techniques, and methods of fighting as a specific enemy—Libya, Russia,
           United States, Germany, North Korea, and so on. The goal of these exercises is to allow
           the pilots to understand enemy attack patterns and to identify and be prepared for cer-
           tain offensive actions, so they can properly react in the correct defensive manner.
               This may seem like a large leap—from pilots practicing for wartime to corporations
           trying to practice proper information security—but it is all about what the team is try-
           ing to protect and the risks involved.
               A military is trying to protect its nation and its assets. Many governments around
           the world have also come to understand that the same assets they have spent millions
           and perhaps billions of dollars to protect physically now face different types of threats.
           The tanks, planes, and weaponry still have to be protected from being blown up, but
           these same tanks, planes, and weaponry are now all run by and are dependent upon
           software. This software can be hacked into, compromised, or corrupted. Coordinates of
           where bombs are to be dropped can be changed. Individual military bases still need to
           be protected by surveillance and military police; this is physical security. Satellites and
           airplanes perform surveillance to watch for suspicious activities taking place from afar,
           and security police monitor the entry points in and out of the base. These types of con-
           trols are limited in monitoring all of the entry points into a military base. Because the
           base is so dependent upon technology and software—as every organization is today—
           and there are now so many communication channels present (Internet, extranets, wire-
           less, leased lines, shared WAN lines, and so on), a different type of “security police” is
           required to cover and monitor all of these entry points into and out of the base.
               Okay, so your corporation does not hold top security information about the tactical
           military troop movement through Afghanistan, you don’t have the speculative coordi-
           nates of the location of bin Laden, and you are not protecting the launch codes of nu-
           clear bombs—does that mean you do not need to have the same concerns and
           countermeasures? Nope. Just as the military needs to protect its assets, you need to
           protect yours.
               An interesting aspect of the hacker community is that it is changing. Over the last
           few years, their motivation has changed from just the thrill of figuring out how to ex-
           ploit vulnerabilities to figuring out how to make revenue from their actions and getting
           paid for their skills. Hackers who were out to “have fun” without any real target in mind
           have, to a great extent, been replaced by people who are serious about gaining financial
           benefits from their activities. Attacks are not only getting more specific, but also in-
           creasing in sophistication. The following are just a few examples of this type of trend:
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                                                                    Chapter 1: Ethics of of Ethical Hacking
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        use of a piece of malware called “Black Energy.” According to Symantec, about
        half of all phishing incidents in 2008 were credited to the RBN.
                                                                                                              PART I
     • A group of Russian, Estonian, and Moldovan hackers were indicted in
       November 2009, after stealing more than $9 million from a credit card
       processor in one day. The hackers were alleged to have broken the encryption
       scheme used at Royal Bank of Scotland’s payment processor, and then they
       raised account limits, created and distributed counterfeit debit cards, and
       withdrew roughly $9.4 million from more than 2,100 ATMs worldwide—in
       less than 12 hours.
     • Hackers using a new kind of malware made off with at least 300,000 Euros
       from German banks in August of 2009. The malware wrote new bank
       statements as it took money from victims’ bank accounts, changing HTML
       coding on an infected machine before a user could see it.
    Criminals are also using online scams in a bid to steal donations made to help
those affected by the January 2010 earthquake in Haiti and other similar disasters.
Fraudsters have set up fictitious websites or are falsely using the names of genuine
charities to trick donors into sending them donations. If you can think of the crime, it
is probably already taking place within the digital world. You can learn more about
these types of crimes at www.cybercrime.gov.
    Malware is still one of the main culprits that costs companies the most amount of
money. An interesting thing about malware is that many people seem to put it in a dif-
ferent category from hacking and intrusions. The fact is malware has evolved to become
one of the most sophisticated and automated forms of hacking. The attacker only has
to put some upfront effort into developing the software, and then with no more effort
required from the attacker, the malware can do its damage over and over again. The
commands and logic within the malware are the same components that attackers used
to have to carry out manually.
    Sadly, many of us have a false sense of security when it comes to malware detection.
In 2006, Australia’s CERT announced that 80 percent of antivirus software products
commonly missed new malware attacks because attackers test their malware software
against the most popular antivirus software products in the industry to hide from detec-
tion. If you compare this type of statistic with the amount of malware that hits the In-
ternet hourly, you can get a sense of the level of vulnerability we are actually faced with.
In 2008, Symantec had to write new virus signatures every 20 seconds to keep up with
the onslaught of malware that was released. This increased to every 8 seconds by 2009.
As of this writing, close to 4 million malware signatures are required for antivirus soft-
ware to be up to date.
    The company Alinean has put together the cost estimates, per minute, for different
organizations if their operations are interrupted. Even if an attack or compromise is not
totally successful for the attacker (he or she does not obtain the desired asset), this in
no way means that the company remains unharmed. Many times attacks and intrusions
cause more of a nuisance and can negatively affect production and the normal depart-
ment operations, which always correlates to costing the company more money in direct
or indirect ways. These costs are shown in Table 1-1.
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             Business Application                                Estimated Outage Cost per Minute
             Supply chain management                             $11,000
             E-commerce                                          $10,000
             Customer service                                    $3,700
             ATM/POS/EFT                                         $3,500
             Financial management                                $1,500
             Human capital management                            $1,000
             Messaging                                           $1,000
            Infrastructure                                       $700
           Table 1-1 Downtime Losses (Source: Alinean)
               A conservative estimate from Gartner pegs the average hourly cost of downtime for
           computer networks at $42,000. A company that suffers from worse than average down-
           time of 175 hours a year can lose more than $7 million per year. Even when attacks are
           not newsworthy enough to be reported on TV or talked about in security industry cir-
           cles, they still negatively affect companies’ bottom lines.
               As stated earlier, an interesting shift has taken place in the hacker community, from
           joy riding to hacking as an occupation. Today, potentially millions of computers are
           infected with bots that are controlled by specific hackers. If a hacker has infected 10,000
           systems, this is her botnet, and she can use it to carry out DDoS attacks or even lease
           these systems to others who do not want their activities linked to their true identities or
           systems. (Botnets are commonly used to spread spam, phishing attacks, and pornogra-
           phy.) The hacker who owns and runs a botnet is referred to as a bot herder. Since more
           network administrators have configured their mail relays properly and blacklists have
           been employed to block mail relays that are open, spammers have had to change tactics
           (using botnets), which the hacking community has been more than willing to pro-
           vide—for a price.
               For example, the Zeus bot variant uses key-logging techniques to steal sensitive data
           such as usernames, passwords, account numbers, and credit card numbers. It injects
           fake HTML forms into online banking login pages to steal user data. Its botnet is esti-
           mated to consist of 3.6 million compromised computers. Zeus’s creators are linked to
           about $100 million in fraud in 2009 alone. Another botnet, the Koobface, is one of the
           most efficient social engineering–driven botnets to date. It spreads via social network-
           ing sites MySpace and Facebook with faked messages or comments from “friends.”
           When a user clicks a provided link to view a video, the user is prompted to obtain a
           necessary software update, like a CODEC—but the update is really malware that can
           take control of the computer. By early 2010, 2.9 million computers have knowingly
           been compromised. Of course, today many more computers have been compromised
           than has been reported.
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                                                                                                   7
Security Compromises and Trends
                                                                                                        PART I
The following are a few specific examples and trends of security compromises
that are taking place today:
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               Some hackers also create and sell zero-day attacks. A zero-day attack is one for which
           there is currently no fix available and whoever is running the particular software that
           contains that exploitable vulnerability is exposed with little or no protection. The code
           for these types of attacks are advertised on special websites and sold to other hackers or
           organized crime rings.
           References
           Alinean www.alinean.com/
           Computer Crime & Intellectual Property Section, United States Department of
           Justice www.cybercrime.gov
           Federal Trade Commission, Identity Theft Site http://www.ftc.gov/bcp/edu/
           microsites/idtheft/
           Infonetics Research www.infonetics.com
           Privacy Rights Clearinghouse, Chronology of Data Breaches, Security Breaches
           2005-Present www.privacyrights.org/ar/ChronDataBreaches.htm#CP
           Robot Wars: How Botnets Work (Massimiliano Romano, Simone Rosignoli,
           and Ennio Giannini for hakin9) www.windowsecurity.com/articles/
           Robot-Wars-How-Botnets-Work.html
           Zero-Day Attack Prevention http://searchwindowssecurity.techtarget.com/
           generic/0,295582,sid45_gci1230354,00.html
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                                                                    Chapter 1: Ethics of of Ethical Hacking
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line for their illegal distribution of copyrighted material. The problem is that many of
these entities just pop up on some other BitTorrent site a few days later. BitTorrent is a
                                                                                                              PART I
common example of a technology that can be used for good and evil purposes.
    Another common gray area in web-based technology is search engine optimization
(SEO). Today, all organizations and individuals want to be at the top of each search
engine result to get as much exposure as possible. Many simple to sophisticated ways
are available for carrying out the necessary tasks to climb to the top. The proper meth-
ods are to release metadata that directly relates to content on your site, update your
content regularly, and create legal links and backlinks to other sites, etc. But, for every
legitimate way of working with search engine algorithms, there are ten illegitimate
ways. Spamdexing offers a long list of ways to fool search engines into getting a specific
site up the ladder in a search engine listing. Then there’s keyword stuffing, in which a
malicious hacker or “black hat” will place hidden text within a page. For example, if
Bob has a website that carries out a phishing attack, he might insert hidden text within
his page that targets elderly people to help drive these types of victims to his site.
    There are scraper sites that take (scrape) content from another website without au-
thorization. The malicious site will make this stolen content unique enough that it
shows up as new content on the Web, thus fooling the search engine into giving it a
higher ranking. These sites commonly contain mostly advertisements and links back to
the original sites.
    There are several other ways of manipulating search engine algorithms as well, for
instance, creating link farms, hidden links, fake blogs, page hijacking, and so on. The
crux here is that some of these activities are the right way of doing things and some of
them are the wrong way of doing things. Our laws have not necessarily caught up with
defining what is legal and illegal all the way down to SEO algorithm activities.
    There are multiple instances of the controversial concept of hactivism. Both legal
and illegal methods can be used to portray political ideology. Is it right to try and influ-
ence social change through the use of technology? Is web defacement covered under
freedom of speech? Is it wrong to carry out a virtual “sit in” on a site that provides il-
legal content? During the 2009 Iran elections, was it unethical for an individual to set
up a site that showed upheaval about the potential corrupt government elections?
When Israeli invaded Gaza, there were many website defacements, DoS attacks, and
website highjackings. The claim of what is ethical versus not ethical probably depends
upon which side the individuals making these calls reside.
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           How Does This Stuff Relate to an
           Ethical Hacking Book?
           Corporations and individuals need to understand how the damage is being done so
           they understand how to stop it. Corporations also need to understand the extent of the
           threat that a vulnerability represents. Let’s take a very simplistic example. The company
           FalseSenseOfSecurity, Inc., may allow its employees to share directories, files, and whole
           hard drives. This is done so that others can quickly and easily access data as needed. The
           company may understand that this practice could possibly put the files and systems at
           risk, but they only allow employees to have unclassified files on their computers, so the
           company is not overly concerned. The real security threat, which is something that
           should be uncovered by an ethical hacker, is if an attacker can use this file-sharing ser-
           vice as access into a computer itself. Once this computer is compromised, the attacker
           will most likely plant a backdoor and work on accessing another, more critical system
           via the compromised system.
                The vast amount of functionality that is provided by an organization’s networking,
           database, and desktop software can be used against them. Within each and every orga-
           nization, there is the all-too-familiar battle of functionality vs. security. This is the rea-
           son that, in most environments, the security officer is not the most well-liked
           individual in the company. Security officers are in charge of ensuring the overall secu-
           rity of the environment, which usually means reducing or shutting off many function-
           alities that users love. Telling people that they cannot access social media sites, open
           attachments, use applets or JavaScript via e-mail, or plug in their mobile devices to a
           network-connected system and making them attend security awareness training does
           not usually get you invited to the Friday night get-togethers at the bar. Instead, these
           people are often called “Security Nazi” or “Mr. No” behind their backs. They are re-
           sponsible for the balance between functionality and security within the company, and
           it is a hard job.
                The ethical hacker’s job is to find these things running on systems and networks,
           and he needs to have the skill set to know how an enemy would use these things against
           the organization. This work is referred to as a penetration test, which is different from
           a vulnerability assessment, which we’ll discuss first.
           Vulnerability Assessment
           A vulnerability assessment is usually carried out by a network scanner on steroids. Some
           type of automated scanning product is used to probe the ports and services on a range
           of IP addresses. Most of these products can also test for the type of operating system
           and application software running and the versions, patch levels, user accounts, and
           services that are also running. These findings are matched up with correlating vulnera-
           bilities in the product’s database. The end result is a large pile of reports that provides a
           list of each system’s vulnerabilities and corresponding countermeasures to mitigate the
           associated risks. Basically, the tool states, “Here is a list of your vulnerabilities and here
           is a list of things you need to do to fix them.”
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                                                                      Chapter 1: Ethics of of Ethical Hacking
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    To the novice, this sounds like an open and shut case and an easy stroll into net-
work utopia where all of the scary entities can be kept out. This false utopia, unfortu-
                                                                                                                PART I
nately, is created by not understanding the complexity of information security. The
problem with just depending upon this large pile of printouts is that it was generated
by an automated tool that has a hard time putting its findings into the proper context
of the given environment. For example, several of these tools provide an alert of “High”
for vulnerabilities that do not have a highly probable threat associated with them. The
tools also cannot understand how a small, seemingly insignificant, vulnerability can be
used in a large orchestrated attack.
    Vulnerability assessments are great for identifying the foundational security issues
within an environment, but many times, it takes an ethical hacker to really test and
qualify the level of risk specific vulnerabilities pose.
Penetration Testing
A penetration test is when ethical hackers do their magic. They can test many of the vul-
nerabilities identified during the vulnerability assessment to quantify the actual threat
and risk posed by the vulnerability.
     When ethical hackers are carrying out a penetration test, their ultimate goal is usu-
ally to break into a system and hop from system to system until they “own” the domain
or environment. They own the domain or environment when they either have root
privileges on the most critical Unix or Linux system or own the domain administrator
account that can access and control all of the resources on the network. They do this to
show the customer (company) what an actual attacker can do under the circumstances
and current security posture of the network.
     Many times, while the ethical hacker is carrying out her procedures to gain total
control of the network, she will pick up significant trophies along the way. These tro-
phies can include the CEO’s passwords, company trade-secret documentation, admin-
istrative passwords to all border routers, documents marked “confidential” held on the
CFO’s and CIO’s laptops, or the combination to the company vault. The reason these
trophies are collected along the way is so the decision makers understand the ramifica-
tions of these vulnerabilities. A security professional can go on for hours to the CEO,
CIO, or COO about services, open ports, misconfigurations, and hacker potential with-
out making a point that this audience would understand or care about. But as soon as
you show the CFO his next year’s projections, or show the CIO all of the blueprints to
the next year’s product line, or tell the CEO that his password is “IAmWearingPanties,”
they will all want to learn more about the importance of a firewall and other counter-
measures that should be put into place.
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               The goal of a vulnerability test is to provide a listing of all of the vulnerabilities
           within a network. The goal of a penetration test is to show the company how these
           vulnerabilities can be used against it by attackers. From here, the security professional
           (ethical hacker) provides advice on the necessary countermeasures that should be im-
           plemented to reduce the threats of these vulnerabilities individually and collectively. In
           this book, we will cover advanced vulnerability tools and methods as well as sophisti-
           cated penetration techniques. Then we’ll dig into the programming code to show you
           how skilled attackers identify vulnerabilities and develop new tools to exploit their
           findings.
               Let’s take a look at the ethical penetration testing process and see how it differs from
           that of unethical hacker activities.
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                                                          Chapter 1: Ethics of of Ethical Hacking
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  • The company’s website and source code
                                                                                                    PART I
  • Social networking sites
  • Whois database
  • Edgar database
  • Newsgroups
  • ARIN, RIPE, APNIC, LACNIC databases
  • Google, Monster.com, etc.
  • Dumpster diving
4. Active scanning Probe the target’s public exposure with scanning tools,
   which might include:
  • Commercial scanning tools
  • Banner grabbing
  • Social engineering
  • War dialing
  • DNS zone transfers
  • Sniffing traffic
  • Wireless war driving
5. Attack surface enumeration Probe the target network to identify,
   enumerate, and document each exposed device:
  • Network mapping
  • Router and switch locations
  • Perimeter firewalls
  • LAN, MAN, and WAN connections
6. Fingerprinting Perform a thorough probe of the target systems to identify:
  • Operating system type and patch level
  • Applications and patch level
  • Open ports
  • Running services
  • User accounts
7. Target system selection Identify the most useful target(s).
8. Exploiting the uncovered vulnerabilities Execute the appropriate attack
   tools targeted at the suspected exposures.
  • Some may not work.
  • Some may kill services or even kill the server.
  • Some may be successful.
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                 9. Escalation of privilege Escalate the security context so the ethical hacker has
                    more control.
                    • Gaining root or administrative rights
                    • Using cracked password for unauthorized access
                    • Carrying out buffer overflow to gain local versus remote control
                10. Documentation and reporting Document everything found, how it was
                    found, the tools that were used, vulnerabilities that were exploited, the
                    timeline of activities, and successes, etc.
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                                                                      Chapter 1: Ethics of of Ethical Hacking
                                                                                                          15
     5. Covering his tracks
                                                                                                                PART I
        • Scrubbing event and audit logs
        • Hiding uploaded files
        • Hiding the active processes that allow the attacker to regain access
        • Disabling messages to security software and system logs to hide malicious
          processes and actions
     6. Hardening the system
        • After taking ownership of a system, an attacker may fix the open
          vulnerabilities so no other attacker can use the system for other purposes.
    How the attacker uses the compromised systems depends upon what his overall
goals are, which could include stealing sensitive information, redirecting financial
transactions, adding the systems to his bot network, extorting a company, etc.
    The crux is that ethical and unethical hackers carry out basically the same activities
only with different intentions. If the ethical hacker does not identify the hole in the
defenses first, the unethical hacker will surely slip in and make himself at home.
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16
           there are tools that allow for ACK packets to be generated and sent, he is only seeing
           part of the picture here. This lack of knowledge and experience allows for a false sense
           of security, which seems to be pretty common in companies around the world today.
               Let’s look at another example. A network engineer configures a firewall to review
           only the first fragment of a packet and not the packet fragments that follow. The engi-
           neer knows that this type of “cut through” configuration will increase network perfor-
           mance. But if she is not aware that there are tools that can create fragments with
           dangerous payloads, she could be allowing in malicious traffic. Once these fragments
           reach the inside destination system and are reassembled, the packet can be put back
           together and initiate an attack.
               In addition, if a company’s employees are not aware of social engineering attacks
           and how damaging they can be, they may happily give out useful information to attack-
           ers. This information is then used to generate even more powerful and dangerous at-
           tacks against the company. Knowledge and the implementation of knowledge are the
           keys for any real security to be accomplished.
               So where do we stand on hacking books and hacking classes? Directly on top of a
           slippery banana peel. There are currently three prongs to the problem of today’s hack-
           ing classes and books. First, marketing people love to use the word “hacking” instead of
           more meaningful and responsible labels such as “penetration methodology.” This
           means that too many things fall under the umbrella of hacking. All of these procedures
           now take on the negative connotation that the word “hacking” has come to be associ-
           ated with. Second is the educational piece of the difference between hacking and ethi-
           cal hacking, and the necessity of ethical hacking (penetration testing) in the security
           industry. The third issue has to do with the irresponsibility of many hacking books and
           classes. If these items are really being developed to help out the good guys, then they
           should be developed and structured to do more than just show how to exploit a vulner-
           ability. These educational components should show the necessary countermeasures
           required to fight against these types of attacks and how to implement preventive mea-
           sures to help ensure these vulnerabilities are not exploited. Many books and courses
           tout the message of being a resource for the white hat and security professional. If you
           are writing a book or curriculum for black hats, then just admit it. You will make just as
           much (or more) money, and you will help eliminate the confusion between the con-
           cepts of hacking and ethical hacking.
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                                                                  Chapter 1: Ethics of of Ethical Hacking
                                                                                                      17
Tool A if attackers do not use Tool A. The ethical hacker has to know what the bad guys
are using, know the new exploits that are out in the underground, and continually keep
                                                                                                            PART I
her skills and knowledgebase up to date. Why? Because the odds are against the com-
pany and against the security professional. The security professional has to identify and
address all of the vulnerabilities in an environment. The attacker only has to be really
good at one or two exploits, or really lucky. A comparison can be made to the U.S.
Homeland Security responsibilities. The CIA and FBI are responsible for protecting the
nation from the 10 million things terrorists could possibly think up and carry out. The
terrorist only has to be successful at one of these 10 million things.
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Gray Hat Hacking, The Ethical Hacker’s Handbook, Third Edition
18
                          NOTE A company’s security policy should state that this type of password-
                          testing activity is allowed by the IT staff and security team. Breaking employees’
                          passwords could be seen as intrusive and wrong if management does not
                          acknowledge and allow for such activities to take place. Make sure you get
                          permission before you undertake this type of activity.
               The same network staff needs to make sure that their firewall and router configura-
           tions will actually provide the protection level that the company requires. They could
           read the manuals, make the configuration changes, implement ACLs, and then go and
           get some coffee. Or they could implement the configurations and then run tests against
           these settings to see if they are allowing malicious traffic into what they thought was a
           controlled environment. These tests often require the use of hacking tools. The tools
           carry out different types of attacks, which allow the team to see how the perimeter de-
           vices will react in certain circumstances.
               Nothing should be trusted until it is tested. There is an amazing number of cases
           where a company does everything seemingly correct when it comes to their infrastruc-
           ture security. They implement policies and procedures, roll out firewalls, IDS, and anti-
           virus, have all of their employees attend security awareness training, and continually
           patch their systems. It is unfortunate that these companies put forth all the right effort
           and funds only to end up on CNN as the latest victim because all of their customers’
           credit card numbers were stolen and posted on the Internet. And this can happen if
           they do not carry out the necessary vulnerability and penetration tests.
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                                                                     Chapter 1: Ethics of of Ethical Hacking
                                                                                                         19
these items will help the company protect itself. The argument can be made that we
have more automated security products that identify these types of activities so that we
                                                                                                               PART I
don’t have to see them coming. But depending upon software that does not have the
ability to put the activities in the necessary context and make a decision is very danger-
ous. Computers can outperform any human on calculations and performing repetitive
tasks, but we still have the ability to make some necessary judgment calls because we
understand the grays in life and do not just see things in 1s and 0s.
    So it is important to understand that hacking tools are really just software tools that
carry out some specific type of procedure to achieve a desired result. The tools can be
used for good (defensive) purposes or for bad (offensive) purposes. The good and the
bad guys use the same exact toolset; the difference is their intent when operating these
utilities. It is imperative for the security professional to understand how to use these
tools and how attacks are carried out if he is going to be of any use to his customer and
to the industry.
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Gray Hat Hacking, The Ethical Hacker’s Handbook, Third Edition
20
               It is not fair to put all of the blame on the programmers, because they have done
           exactly what their employers and market have asked them to: quickly build applica-
           tions with tremendous functionality. Only over the last few years has the market started
           screaming for functionality and security, and the vendors and programmers are scram-
           bling to meet these new requirements and still stay profitable.
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                                                                  Chapter 1: Ethics of of Ethical Hacking
                                                                                                      21
    Will it get worse before it gets better? Probably. Every industry in the world is be-
coming more reliant on software and technology. Software vendors have to carry out
                                                                                                            PART I
the continual one-upmanship to ensure their survivability in the market. Although se-
curity is becoming more of an issue, functionality of software has always been the main
driving component of products, and it always will be. Attacks will also continue and
increase in sophistication because they are now revenue streams for individuals, com-
panies, and organized crime groups.
    Will vendors integrate better security, ensure their programmers are properly trained
in secure coding practices, and put each product through more and more testing cycles?
Not until they have to. Once the market truly demands that this level of protection and
security is provided by software products and customers are willing to pay more for
security, then the vendors will step up to the plate. Currently, most vendors are only
integrating protection mechanisms because of the backlash and demand from their
customer bases. Unfortunately, just as September 11th awakened the United States to its
vulnerabilities, something large may have to take place in terms of software compro-
mise before the industry decides to address this issue properly.
    So we are back to the original question: what does this have to do with ethical hack-
ing? A novice ethical hacker will use tools developed by others who have uncovered
specific vulnerabilities and methods to exploit them. A more advanced ethical hacker
will not just depend upon other people’s tools, she will have the skill set and under-
standing to look at the code itself. The more advanced ethical hacker will be able to
identify possible vulnerabilities and programming code errors and develop ways to rid
the software of these types of flaws.
    If the software did not contain 5–50 exploitable bugs within every 1,000 lines of
code, we would not have to build the fortresses we are constructing today. Use this book
as a guide to bring you deeper and deeper under the covers to allow you to truly under-
stand where the security vulnerabilities reside and what should be done about them.
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often spoken at home, to meet them. Cathalina was making a low
bow to her aunt and presenting her diploma.
   “Have it framed, Auntie! Put it in Uncle Morris’s collection of
pictures; it has one of Greycliff on it.”
   “You have earned it. I think we shall let you put it away among
the Van Buskirk archives,” returned Aunt Katherine.
   But there was still packing to be done. After a lunch, rather more
elaborate than usual, the girls scattered to their rooms and the
exodus began. Another year at Greycliff was completed.
                             THE END
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