Pentesting Prompts
~/Web Security/Authentication Bypass Techniques
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Web Security
Intermediateweb-security

Authentication Bypass Techniques

prompt

You are testing a web application's authentication mechanisms during an authorized penetration test.

**Login Bypass**
- How do you test a login form for SQL injection authentication bypass?
- What is a type juggling vulnerability and in which languages does it appear? (PHP == vs ===)
- What is a mass assignment vulnerability and how does it affect authentication?
- How do you test for authentication bypass via HTTP method tampering?

**Password Reset Flaws**
- What are the most common password reset vulnerabilities? (predictable tokens, host header injection, user enumeration)
- How does a host header injection in password reset emails work?
- How do you test for token expiry and single-use enforcement?
- What is a password reset poisoning attack?

**Multi-Factor Authentication Bypass**
- How do you test for MFA bypass via OTP brute force when rate limiting is absent?
- What is a response manipulation bypass for MFA? (changing failed=true to failed=false)
- How do you test for MFA bypass via account recovery flows?

**Session Management**
- How do you test for predictable session token values?
- What does session fixation mean and how do you test for it?
- How do you test for session token leakage? (Referer header, URL parameters, logs)
- What is a CSRF attack and how do you identify missing CSRF protection?

**OAuth2 & SSO**
- How do you test an OAuth2 flow for open redirect exploitation?
- What is a SAML authentication bypass? (XML signature wrapping)
- How do you test for SSO token reuse across applications?

Output:
- Authentication bypass checklist
- Common vulnerability patterns with example payloads
- Burp Suite workflow for auth testing

You are testing a web application's authentication mechanisms during an authorized penetration test.

Login Bypass

  • How do you test a login form for SQL injection authentication bypass?
  • What is a type juggling vulnerability and in which languages does it appear? (PHP == vs ===)
  • What is a mass assignment vulnerability and how does it affect authentication?
  • How do you test for authentication bypass via HTTP method tampering?

Password Reset Flaws

  • What are the most common password reset vulnerabilities? (predictable tokens, host header injection, user enumeration)
  • How does a host header injection in password reset emails work?
  • How do you test for token expiry and single-use enforcement?
  • What is a password reset poisoning attack?

Multi-Factor Authentication Bypass

  • How do you test for MFA bypass via OTP brute force when rate limiting is absent?
  • What is a response manipulation bypass for MFA? (changing failed=true to failed=false)
  • How do you test for MFA bypass via account recovery flows?

Session Management

  • How do you test for predictable session token values?
  • What does session fixation mean and how do you test for it?
  • How do you test for session token leakage? (Referer header, URL parameters, logs)
  • What is a CSRF attack and how do you identify missing CSRF protection?

OAuth2 & SSO

  • How do you test an OAuth2 flow for open redirect exploitation?
  • What is a SAML authentication bypass? (XML signature wrapping)
  • How do you test for SSO token reuse across applications?

Output:

  • Authentication bypass checklist
  • Common vulnerability patterns with example payloads
  • Burp Suite workflow for auth testing