Open Source Pentest Documents

Press 's' to show speaker notes…​

This slide deck is intended to be edited and used in a pitch to a partner, client or customer and is released under the Creative Commons Zero v1.0 license.

Thank you to all the contributors that make these documents amazing.

Agenda

  1. Terminology

  2. Mindset

  3. Communications

  4. Common Fears

  5. Methodology

  6. Scenarios

  7. Addons

Terminology

What is Pentesting?

Engagement type that targets a computer, network or web application infrastructure for a company.

This type of engagement focuses on the prevention security layer. Finding, testing, classifying, and verifying vulnerabilities in the company’s environment

What is Red Teaming?

Team based engagements that includes the IT, social, and physical verticals. This type of engagements focus on all three layers of security defense, prevention, detection, and response. Findings focus on systemic, broad spectrum vulnerabilities in narrative format.

Scenarios

Breach Simulation

BS: Description

BS: Goals

Black Box

BB: Description

BB: Goals

Stolen Device

SD: Description

SD: Goals

Opportunistic Attacker

(1 week)

OA: Description

  • Loud (no stealth)

  • Techniques

    • Login brute forcing

    • Fast / Large port range Nmap scanning

    • Vuln scanning / Web vuln scanning

    • SPAM style phishing

  • Separating attack techniques by day for ease of identification

OA: Goals

  • Identify IT security maturity level

  • Test prevention security layer

    • AV / HIPS

    • Proxy services

    • Web Application Firewalls

    • SPAM / Phishing filters

  • Active or Post-Engagement Detection just to see if capabilities are working and can see “loud” attacks

External w/ Credentials

EW/C: Description

  • Login Attempts

    • Company web login interfaces

    • VPN / Remote Access interfaces

    • Email interfaces

    • External / Cloud interfaces (Office365, Dropbox, Box, etc)

    • External / Cloud infrastructure (AWS, Azure)

  • Attempts to obtain code execution

    • If obtained, post-exploitation is in-scope to better identify impact of scenario

EW/C: Goals

  • Identify authentication leak risk to the enterprise via stolen, backdoored, or disgruntled employee

  • Identify previously unknown authentication interfaces

  • Test prevention security layer

    • 2-Factor Authentication / Multi-Factor Authentication

  • Test detection security layer

    • Foreign / suspicious login identification / alerting

Add-Ons

CxO Breach Training

Password Auditing

Wireless

Social Engineering

Physical

Egress Testing

Detection Collaboration

C2 Detection Exercise

Rogue Device

Table Top

Vendor Proving Ground