Security Testing Python Web Applications (SECT-PYWA) – Outline

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DAY 1

Cyber security basics

  • What is security?
  • Threat and risk
  • Cyber security threat types
  • Consequences of insecure software
    • Constraints and the market
    • The dark side

The OWASP Top Ten

  • OWASP Top 10 – 2017
  • A1 – Injection
    • Injection principles
    • Injection attacks
    • SQL injection
      • SQL injection basics
      • Lab – SQL injection
      • Attack techniques
      • Content-based blind SQL injection
      • Time-based blind SQL injection
      • Case study – Hacking Fortnite accounts
      • Testing for SQL injection
    • Code injection
      • Code injection via input()
      • OS command injection
        • Lab – Command injection
        • Case study – Shellshock
        • Lab – Shellshock
        • Case study – Command injection via ping
        • Testing for command injection
      • Script injection
        • Server-side template injection (SSTI)
        • Lab – Template injection
  • A2 – Broken Authentication
    • Authentication basics
    • Multi-factor authentication
    • Authentication weaknesses – spoofing
    • Spoofing on the Web
    • Testing for weak authentication
    • Case study – PayPal 2FA bypass
    • User interface best practices
    • Lab – On-line password brute forcing
    • Password management
      • Inbound password management
        • Storing account passwords
        • Password in transit
        • Lab – Is just hashing passwords enough?
        • Dictionary attacks and brute forcing
        • Salting
        • Adaptive hash functions for password storage
        • Password policy
          • NIST authenticator requirements for memorized secrets
          • Password length
          • Password hardening
          • Using passphrases
        • Case study – The Ashley Madison data breach
          • The dictionary attack
          • The ultimate crack
          • Exploitation and the lessons learned
          • (Mis)handling None passwords
          • Testing for password management issues

DAY 2

Security testing

  • Security testing vs functional testing
  • Manual and automated methods
  • Security testing methodology
    • Security testing – goals and methodologies
    • Overview of security testing processes
    • Identifying and rating assets
      • Preparation
      • Identifying assets
      • Identifying the attack surface
      • Assigning security requirements
      • Lab – Identifying and rating assets
    • Threat modeling
      • SDL threat modeling
      • Mapping STRIDE to DFD
      • DFD example
      • Attack trees
      • Attack tree example
      • Lab – Crafting an attack tree
      • Misuse cases
      • Misuse case examples
      • Risk analysis
      • Lab – Risk analysis
    • Security testing approaches
      • Reporting, recommendations, and review

The OWASP Top Ten

  • A3 – Sensitive Data Exposure
    • Information exposure
    • Exposure through extracted data and aggregation
    • Case study – Strava data exposure
    • Error and exception handling principles
    • Information exposure through error reporting
    • Information leakage via error pages
    • Lab – Flask information leakage
  • A4 – XML External Entities (XXE)
    • DTD and the entities
    • Entity expansion
    • Lab – Billion laughs attack
    • External Entity Attack (XXE)
      • File inclusion with external entities
      • Server-Side Request Forgery with external entities
      • Lab – External entity attack
      • Case study – XXE vulnerability in SAP Store
      • Preventing XXE
  • A5 – Broken Access Control
    • Access control basics
    • Failure to restrict URL access
    • Testing for authorization issues
    • Confused deputy
      • Insecure direct object reference (IDOR)
      • Lab – Insecure Direct Object Reference
      • Authorization bypass through user-controlled keys
      • Case study – Authorization bypass on Facebook
      • Lab – Horizontal authorization
      • Testing for confused deputy weaknesses
    • File upload
      • Unrestricted file upload
      • Good practices
      • Lab – Unrestricted file upload
      • Testing for file upload vulnerabilities
  • A6 – Security Misconfiguration
    • Configuration principles
    • Configuration management
    • Python configuration best practices
      • Configuring Flask
      • Testing for misconfiguration issues
  • A7 – Cross-site Scripting (XSS)
    • Cross-site scripting basics
    • Cross-site scripting types
      • Persistent cross-site scripting
      • Reflected cross-site scripting
      • Client-side (DOM-based) cross-site scripting
      • Lab – Stored XSS
      • Lab – Reflected XSS
      • Case study – XSS in Fortnite accounts
      • Additional protection layers
      • Testing for XSS

DAY 3

The OWASP Top Ten

  • A8 – Insecure Deserialization
    • Serialization and deserialization challenges
    • Deserializing untrusted streams
    • Deserialization with pickle
    • Lab – Deserializing with Pickle
    • PyYAML deserialization challenges
    • Testing for insecure deserialization
  • A9 – Using Components with Known Vulnerabilities
    • Using vulnerable components
    • Assessing the environment
    • Hardening
    • Untrusted functionality import
    • Malicious packages in Python
    • Importing JavaScript
    • Lab – Importing JavaScript
    • Case study – The British Airways data breach
    • Vulnerability management
      • Patch management
      • Bug bounty programs
      • Vulnerability databases
      • Vulnerability rating – CVSS
      • DevOps, the build process and CI / CD
      • Dependency checking in Python
      • Lab – Detecting vulnerable components
  • A10 – Insufficient Logging & Monitoring
    • Logging and monitoring principles
    • Insufficient logging
    • Plaintext passwords at Facebook
    • Firewalls and Web Application Firewalls (WAF)
    • Intrusion detection and prevention
    • Case study – The Marriott Starwood data breach
  • Web application security beyond the Top Ten
    • Client-side security
    • Lab – Client-side security
    • Tabnabbing
    • Lab – Reverse tabnabbing
    • Frame sandboxing
      • Cross-Frame Scripting (XFS) attack
      • Lab – Clickjacking
      • Clickjacking beyond hijacking a click
    • Some further best practices
      • HTML5 security best practices
      • CSS security best practices
      • Ajax security best practices

Security testing

  • Security testing techniques and tools
    • Code analysis
      • Security aspects of code review
      • Static Application Security Testing (SAST)
      • Lab – Using static analysis tools
    • Dynamic analysis
      • Security testing at runtime
      • Penetration testing
      • Stress testing
      • Dynamic analysis tools
        • Dynamic Application Security Testing (DAST)
        • Web vulnerability scanners
        • Lab – Using web vulnerability scanners
        • SQL injection tools
        • Lab – Using SQL injection tools
        • Proxy servers
      • Fuzzing

Common software security weaknesses

  • Input validation
    • Input validation principles
      • Lab – Input validation
      • Encoding challenges
      • Lab – Encoding challenges
      • Validation with regex
      • Regular expression denial of service (ReDoS)
      • Lab – Regular expression denial of service (ReDoS)
      • Dealing with ReDoS
    • Files and streams
      • Path traversal
      • Path traversal-related examples
      • Lab – Path traversal
      • Additional challenges in Windows
      • Path traversal best practices
      • Testing for path traversal
      • Format string issues
    • Unsafe native code
      • Native code dependence
      • Lab – Unsafe native code
      • Best practices for dealing with native code

Wrap up

  • And now what?
    • Software security sources and further reading
    • Python resources
    • Security testing resources