Pentesting Prompts
~/Reconnaissance/Social Engineering Reconnaissance
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Social Engineering Reconnaissance

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You are authorized to conduct social engineering reconnaissance as part of a red team engagement. Plan the information gathering phase before any social engineering attempt.

**Target Employee Profiling**
- What OSINT sources provide the most valuable employee information? (LinkedIn, Twitter/X, GitHub, company bios)
- How do you build a realistic pretext using information found about specific employees?
- What does an employee's public content reveal about their technical knowledge level?

**Organizational Mapping**
- How do you map the organizational hierarchy using publicly available information?
- How do you identify which employees handle IT, finance, HR, and executive functions?
- What org chart information is typically visible on LinkedIn and how is it useful for pretexts?

**Pretext Development**
- What makes a pretext believable vs obviously suspicious?
- How do you use legitimate company information (email format, tools used, ongoing projects) to build credibility?
- What is a believable pretense for contacting IT helpdesk vs a CEO's assistant?

**Information Security Posture Indicators**
- What does a company's public security policy page, bug bounty program, and security job listings reveal?
- How do security-related job postings expose defensive tooling and monitoring capabilities?
- What does the absence of a security awareness program suggest?

**Scope & Ethics**
- What does explicit authorization for social engineering look like in an engagement contract?
- How do you document social engineering activities for the report?
- What is the difference between authorized vishing/phishing testing and unauthorized manipulation?

Output:
- Employee profiling checklist
- Pretext quality checklist (what makes it believable)
- Social engineering scope documentation requirements

You are authorized to conduct social engineering reconnaissance as part of a red team engagement. Plan the information gathering phase before any social engineering attempt.

Target Employee Profiling

  • What OSINT sources provide the most valuable employee information? (LinkedIn, Twitter/X, GitHub, company bios)
  • How do you build a realistic pretext using information found about specific employees?
  • What does an employee's public content reveal about their technical knowledge level?

Organizational Mapping

  • How do you map the organizational hierarchy using publicly available information?
  • How do you identify which employees handle IT, finance, HR, and executive functions?
  • What org chart information is typically visible on LinkedIn and how is it useful for pretexts?

Pretext Development

  • What makes a pretext believable vs obviously suspicious?
  • How do you use legitimate company information (email format, tools used, ongoing projects) to build credibility?
  • What is a believable pretense for contacting IT helpdesk vs a CEO's assistant?

Information Security Posture Indicators

  • What does a company's public security policy page, bug bounty program, and security job listings reveal?
  • How do security-related job postings expose defensive tooling and monitoring capabilities?
  • What does the absence of a security awareness program suggest?

Scope & Ethics

  • What does explicit authorization for social engineering look like in an engagement contract?
  • How do you document social engineering activities for the report?
  • What is the difference between authorized vishing/phishing testing and unauthorized manipulation?

Output:

  • Employee profiling checklist
  • Pretext quality checklist (what makes it believable)
  • Social engineering scope documentation requirements