Social Engineering Penetration Testing

Social Engineering Penetration Testing

Executing Social Engineering Pen Tests, Assessments and Defense

1st Edition - April 11, 2014

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  • Authors: Gavin Watson, Andrew Mason, Richard Ackroyd
  • eBook ISBN: 9780124201828
  • Paperback ISBN: 9780124201248

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Social engineering attacks target the weakest link in an organization's security human beings. Everyone knows these attacks are effective, and everyone knows they are on the rise. Now, Social Engineering Penetration Testing gives you the practical methodology and everything you need to plan and execute a social engineering penetration test and assessment. You will gain fascinating insights into how social engineering techniques including email phishing, telephone pretexting, and physical vectors can be used to elicit information or manipulate individuals into performing actions that may aid in an attack. Using the book's easy-to-understand models and examples, you will have a much better understanding of how best to defend against these attacks. The authors of Social Engineering Penetration Testing show you hands-on techniques they have used at RandomStorm to provide clients with valuable results that make a real difference to the security of their businesses. You will learn about the differences between social engineering pen tests lasting anywhere from a few days to several months. The book shows you how to use widely available open-source tools to conduct your pen tests, then walks you through the practical steps to improve defense measures in response to test results.

Key Features

  • Understand how to plan and execute an effective social engineering assessment
  • Learn how to configure and use the open-source tools available for the social engineer
  • Identify parts of an assessment that will most benefit time-critical engagements
  • Learn how to design target scenarios, create plausible attack situations, and support various attack vectors with technology
  • Create an assessment report, then improve defense measures in response to test results


Information security practitioners, information technology leaders, network administrators, computer system administrators, information security engineers, IT professionals, Information security managers, security analysts, and an academic audience among information security majors

Table of Contents

    • Foreword
    • Acknowledgements
    • About the Authors
    • About the Technical Editor
    • Chapter 1. An Introduction to Social Engineering
      • Introduction
      • Defining social engineering
      • Examples from the movies
      • Famous social engineers
      • Real-world attacks
      • Summary
    • Chapter 2. The Weak Link in the Business Security Chain
      • Introduction
      • Why personnel are the weakest link
      • Summary
    • Chapter 3. The Techniques of Manipulation
      • Introduction
      • Pretexting
      • Impersonation
      • Baiting
      • Pressure and solution
      • Leveraging authority
      • Reverse social engineering
      • Chain of authentication
      • Gaining credibility
      • From innocuous to sensitive
      • Priming and loading
      • Social proof
      • Framing information
      • Emotional states
      • Selective attention
      • Personality types and models
      • Body language
      • Summary
    • Chapter 4. Short and Long Game Attack Strategies
      • Introduction
      • Short-term attack strategies
      • Long-term attack strategies
      • Summary
    • Chapter 5. The Social Engineering Engagement
      • Introduction
      • The business need for social engineering
      • Social engineering operational considerations and challenges
      • Challenges for the social engineers
      • Challenges for the client
      • Legislative considerations
      • Social engineering frameworks
      • Assessment prerequisites
      • Key deliverables
      • Social engineering team members and skill sets
      • Summary
    • Chapter 6. Ensuring Value Through Effective Threat Modeling
      • Introduction
      • Why the need for threat modeling?
      • Who would want to gain access to my business?
      • Summary
    • Chapter 7. Creating Targeted Scenarios
      • Introduction
      • The components of a scenario
      • Target identification
      • Pretext design mapping
      • Planning for the unknown
      • Designing to fail
      • Summary
    • Chapter 8. Leveraging Open-Source Intelligence
      • Introduction
      • The corporate website
      • E-mail addresses
      • Social media
      • DNS records
      • Summary
    • Chapter 9. The E-mail Attack Vector
      • Introduction
      • An introduction to phishing attacks
      • Why phishing attacks work
      • Spear phishing versus trawling
      • Spear phishing
      • Real-world phishing examples
      • American Express—drive-by-download
      • Dr. Atanasoff Gavin—advance fee fraud
      • Apple ID scam—credential harvesting
      • Nobody falls for this one. Nobody. Ever.
      • Active e-mail reconnaissance
      • Nondelivery reports
      • Out-of-office responses
      • The nonexistent meeting
      • Impersonating the absent staff member
      • Creating plausible e-mail scenarios
      • Work experience placements
      • Weaponizing the scenario
      • The college project
      • Weaponizing the scenario
      • The recruitment consultant
      • Salesperson
      • Defending against phishing attacks
      • Technological approaches
      • Human approaches
      • Setting up your own attack
      • Spoofed e-mails versus fake domain names
      • The SET
      • Spear phishing attack vector
      • Does this approach really work?
      • Malicious Java applets
      • Using cloned web sites to harvest credentials
      • Is all of this really social engineering?
      • Summary
    • Chapter 10. The Telephone Attack Vector
      • Introduction
      • Real-world examples
      • Environmental sounds
      • The issues with caller ID
      • Caller ID spoofing
      • Phone system hacks
      • Is the contact database up to date?
      • Transferring caller ID
      • How to figure out if your caller ID shows up
      • Summing it up
      • Building on the e-mail attack
      • Please contact Sarah in my absence
      • Who ya gonna call?
      • Job enquiries
      • Sales calls
      • Surveys
      • Impersonating staff members
      • The help desk
      • Employee numbers
      • Obtaining key information and access
      • Credentials and e-mail access
      • Physical access
      • The physical access zero day
      • Weaponizing your call
      • Summary
    • Chapter 11. The Physical Attack Vector
      • Introduction
      • Building on the e-mail and telephone attacks
      • Active information gathering
      • Props and disguises
      • Badges and lanyards
      • Tailgating
      • Lock picking
      • Once you’re inside
      • Summary
    • Chapter 12. Supporting an Attack with Technology
      • Introduction
      • Summary
    • Chapter 13. Writing the Report
      • Introduction
      • Data collection
      • Writing the report
      • Delivery of the report
      • Summary
    • Chapter 14. Creating Hardened Policies and Procedures
      • Introduction
      • Background
      • Social engineering defense: a proactive approach
      • Industry information security and cyber security standards
      • Developing fit for purpose social engineering policies and procedures
      • Summary
    • Chapter 15. Staff Awareness and Training Programs
      • Introduction
      • Current awareness training
      • A model for effective training
      • Summary
    • Chapter 16. Internal Social Engineering Assessments
      • Introduction
      • The need for internal testing
      • Designing the internal test
      • Summary
    • Chapter 17. Social Engineering Assessment Cheat Sheet
      • Introduction
      • Social engineering framework
      • Social engineering cheat sheet
      • Summary
    • Index

Product details

  • No. of pages: 390
  • Language: English
  • Copyright: © Syngress 2014
  • Published: April 11, 2014
  • Imprint: Syngress
  • eBook ISBN: 9780124201828
  • Paperback ISBN: 9780124201248

About the Authors

Gavin Watson

Gavin is the Professional Services Manager at RandomStorm and is responsible for devising and also delivering innovative testing services offered to clients, including the full range of penetration testing and social engineering engagements. Gavin has worked in IT for many years, focusing for the past five years on delivering internal and external penetration tests and social engineering engagements for multiple clients across all verticals.

Affiliations and Expertise

Professional Services Manager at RandomStorm

Andrew Mason

Andrew is the co-founder and Technical Director at RandomStorm and is responsible for the formulation and execution of strategy for the technical department within RandomStorm. Andrew has over 20 years experience in IT with recent years focused on Internet security, offering board-level consultancy to numerous enterprise customers within disparate geographical regions. Andrew has authored several infosec titles for McGraw Hill and Cisco Press. His most recent publications have been focused on Firewalls and Threat Mitigation from common vulnerabilities. Andrew has also contributed to several books on networking topics as well as writing numerous articles for online and print trade journals and newspapers including the Sunday Times. Based in the UK, RandomStorm is a global infosec services consultancy providing turnkey solutions to organizations of any size. RandomStorm has offices in UK, US, Canada, Jordan and UAE.

Affiliations and Expertise

Co-founder and Technical Director at RandomStorm

Richard Ackroyd

Richard is a Senior Security Engineer for RandomStorm and is involved in the conducting penetration testing and social engineering assessments for clients across all verticals.

Affiliations and Expertise

Senior Security Engineer for RandomStorm

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