secure-agent-playbook

Play: OWASP Top 10 Web Security Review

Review web applications against the OWASP Top 10 for Web Applications (2021), producing actionable findings with severity ratings and remediation guidance.

Trigger Conditions

Use this play when:

• Auditing a web application (monolith, microservices, or serverless)
• Reviewing server-side web code for security vulnerabilities
• A user asks for an “OWASP Top 10 review” or “web security assessment”
• Assessing a web framework or CMS for security posture
• Performing a pre-deployment security review of a web app

Inputs

• Web application source code (frontend and backend)
• Framework/language information (React, Django, Rails, etc.)
• Deployment context (internet-facing, internal, cloud platform)
• Authentication/authorization implementation details
• (Optional) Previous security assessments or pentest reports

Procedure

1. Application Mapping

Before assessing risks, understand the application:

Aspect	Questions
Framework	What language/framework? (Node.js/Express, Python/Django, Ruby/Rails, Java/Spring, PHP/Laravel, etc.)
Architecture	Monolith, microservices, serverless (Lambda/Cloud Functions), SPA vs SSR?
Trust Boundary	Internet-facing, internal network, or local-only?
Data Sensitivity	Does it handle PII, credentials, financial data, health data (HIPAA)?
Authentication	Session-based, JWT, OAuth, SSO, API keys?
Data Stores	SQL database, NoSQL, cache (Redis), file storage, external APIs?

Document the attack surface: entry points, data flows, trust boundaries.

2. Assess Each OWASP Top 10 Risk

A01: Broken Access Control

CWE-200, CWE-201, CWE-352, CWE-639

What to Look For:

• Missing authorization checks — Endpoints or functions accessible without verifying user permissions
• IDOR (Insecure Direct Object References) — Can User A access User B’s data by changing IDs in URLs/parameters?
• Privilege escalation — Can regular users access admin functions? Can users elevate their own privileges?
• Path traversal — Can file paths include ../ to escape intended directories?
• CORS misconfiguration — Overly permissive CORS allowing cross-origin attacks
• Forced browsing — Can unauthenticated users access protected resources by guessing URLs?
• JWT token issues — Missing signature validation, algorithm confusion attacks
• Broken function-level authorization — Different auth requirements for UI vs API endpoints

Testing Approach:

1. Map all endpoints requiring authentication
2. Test each without authentication (should fail)
3. Test cross-user access (User A accessing User B’s resources)
4. Test privilege escalation paths (user → admin)
5. Verify authorization on every object access, not just initial authentication

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A02: Cryptographic Failures

CWE-261, CWE-296, CWE-310, CWE-319, CWE-326, CWE-327, CWE-916

What to Look For:

• Weak algorithms — MD5, SHA1 for passwords; DES, RC4 for encryption; ECB mode
• Missing TLS — HTTP instead of HTTPS, weak TLS versions (<1.2), insecure ciphers
• Hardcoded credentials/keys — API keys, database passwords, encryption keys in source code
• Improper key management — Keys stored in version control, no key rotation, weak key generation
• Cleartext transmission — Sensitive data sent over unencrypted channels
• Cleartext storage — Passwords, tokens, or PII stored without encryption
• Insufficient randomness — Predictable tokens, session IDs, or nonces
• Missing integrity checks — Unsigned or unvalidated data that could be tampered with

Testing Approach:

1. Search for hardcoded secrets using patterns (see secrets-scan.md)
2. Verify TLS configuration (certificates, protocol versions, cipher suites)
3. Check password storage (should use bcrypt, Argon2, or PBKDF2)
4. Validate encryption implementations (no custom crypto)
5. Test for sensitive data in URLs, headers, and logs

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A03: Injection

CWE-74, CWE-78, CWE-79, CWE-89, CWE-91, CWE-564, CWE-943

What to Look For:

Injection Type	Indicators	Impact
SQL Injection	String concatenation in SQL, cursor.execute(f"SELECT * FROM users WHERE id = {user_id}"), dynamic queries	Data exfiltration, authentication bypass, RCE
NoSQL Injection	Unsanitized JSON in MongoDB queries, $where clauses with user input	Data manipulation, authentication bypass
OS Command Injection	exec(), system(), subprocess.call() with user input	Remote code execution
LDAP Injection	User input in LDAP filters without escaping	Authentication bypass, data access
XSS (Cross-Site Scripting)	User input rendered without encoding, innerHTML, dangerouslySetInnerHTML, unescaped template output	Session hijacking, credential theft, defacement
SSTI (Server-Side Template Injection)	User input in Jinja2, ERB, EJS templates	RCE, file access
XPath Injection	User input in XPath queries	XML data access
Log Injection	CRLF in log entries (\n\r), log forging	Log tampering, data exfiltration
Header Injection	CRLF in HTTP headers	Response splitting, XSS

Testing Approach:

1. Search for dangerous functions (concatenation, eval, exec, innerHTML)
2. Test each input field with injection payloads
3. Verify output encoding for all user-controlled data
4. Check prepared statements/parameterized queries usage
5. Validate Content Security Policy (CSP) headers for XSS mitigation

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A04: Insecure Design

CWE-73, CWE-183, CWE-209, CWE-213, CWE-235, CWE-256, CWE-257, CWE-266, CWE-269, CWE-280, CWE-434, CWE-444, CWE-501, CWE-522, CWE-697, CWE-799, CWE-807, CWE-840, CWE-841, CWE-927, CWE-1021, CWE-1173, CWE-1174, CWE-1233

What to Look For:

• Missing threat modeling — No documented attack surface, trust boundaries, or threat actors
• Business logic flaws — Workflow bypasses (skip payment step), race conditions (TOCTOU), price manipulation
• Insecure workflows — Missing confirmation steps for destructive actions, no CSRF protection on state changes
• Lack of rate limiting — Brute force vulnerabilities on login, password reset, or sensitive operations
• Insufficient validation — Client-side only validation, missing server-side checks
• Insecure defaults — Debug mode enabled, verbose errors in production, default credentials
• Trust without verification — Trusting client-provided data (prices, user IDs, permissions)
• Missing defense in depth — Single point of failure for security controls

Testing Approach:

1. Review architecture documentation for security considerations
2. Test business logic flows for bypass opportunities
3. Check for race conditions in multi-step processes
4. Verify rate limiting on sensitive endpoints
5. Ensure all validation happens server-side

---

A05: Security Misconfiguration

CWE-2, CWE-11, CWE-13, CWE-15, CWE-16, CWE-209, CWE-250, CWE-260, CWE-312, CWE-497, CWE-538, CWE-540, CWE-541, CWE-547, CWE-611, CWE-614, CWE-756, CWE-942

What to Look For:

• Default configurations — Default passwords, default admin accounts, sample applications deployed
• Verbose error messages — Stack traces, internal paths, SQL errors exposed to users
• Missing security headers — No X-Content-Type-Options, X-Frame-Options, Content-Security-Policy, Strict-Transport-Security
• Unnecessary features — Unused ports open, unnecessary services running, debug endpoints enabled
• Directory listing — Web servers showing directory contents
• Outdated software — Old framework versions, unpatched components
• Cloud misconfigurations — Exposed S3 buckets, open security groups, public databases
• Missing hardening — Default SSL/TLS settings, unnecessary HTTP methods enabled

Testing Approach:

1. Review configuration files (nginx.conf, .htaccess, application.yml)
2. Check for default credentials and accounts
3. Verify security headers using tools or manual inspection
4. Test error handling (trigger errors, check responses)
5. Scan for unnecessary open ports and services
6. Check cloud configurations for public exposure

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A06: Vulnerable and Outdated Components

CWE-937, CWE-1035, CWE-1104

What to Look For:

• Unpatched dependencies — Known CVEs in libraries (see sca-audit.md)
• Unsupported software — End-of-life frameworks, operating systems, databases
• Missing SBOM — No inventory of software components
• Unused dependencies — Dead code increasing attack surface
• Transitive vulnerabilities — Vulnerabilities in dependencies of dependencies
• Supply chain risks — Typosquatting, malicious packages, compromised dependencies

Testing Approach:

1. Run SCA scanner (osv-scanner, npm audit, pip-audit)
2. Review dependency files (package.json, requirements.txt, etc.)
3. Check for end-of-life components
4. Verify dependency update processes
5. Review lockfiles for reproducible builds

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A07: Identification and Authentication Failures

CWE-287, CWE-288, CWE-290, CWE-294, CWE-295, CWE-297, CWE-300, CWE-302, CWE-304, CWE-306, CWE-307, CWE-346, CWE-384, CWE-521, CWE-613, CWE-620, CWE-640, CWE-798, CWE-940, CWE-1216

What to Look For:

• Weak password policy — No minimum length, no complexity requirements, common passwords allowed
• Credential stuffing — No protection against automated login attempts using breached credentials
• Brute force — No rate limiting or account lockout on authentication endpoints
• Session vulnerabilities — Predictable session IDs, session fixation, missing HttpOnly/Secure flags
• Missing MFA — No multi-factor authentication for sensitive accounts
• Weak session management — Sessions don’t expire, no concurrent session limits
• Insecure password recovery — Weak reset tokens, predictable questions, unverified email changes
• JWT issues — None algorithm allowed, weak signing keys, missing expiration

Testing Approach:

1. Test password requirements and complexity
2. Attempt credential stuffing with known breached credentials
3. Test for brute force protection (rate limiting, CAPTCHA, lockout)
4. Analyze session handling (cookies, tokens, expiration)
5. Test password reset flows for security
6. Verify MFA implementation and bypass opportunities

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A08: Software and Data Integrity Failures

CWE-345, CWE-353, CWE-426, CWE-494, CWE-502, CWE-565, CWE-784, CWE-829, CWE-830, CWE-915

What to Look For:

• Insecure deserialization — Deserializing untrusted data (Python pickle, Java ObjectInputStream, PHP unserialize)
• Unsigned updates — Software updates without integrity verification
• CI/CD attacks — Unprotected build pipelines, compromised build agents
• Dependency confusion — Internal packages with names matching public packages
• Unsigned commits — No signature verification on code commits
• Tamper-evident logs — No integrity protection for audit logs
• XML external entities (XXE) — XML parsers with external entity processing enabled

Testing Approach:

1. Search for deserialization functions with user-controlled input
2. Verify update mechanisms include signature verification
3. Review CI/CD configurations for security controls
4. Check for XXE vulnerabilities in XML parsing
5. Verify integrity checks on critical data

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A09: Security Logging and Monitoring Failures

CWE-117, CWE-223, CWE-532, CWE-778, CWE-1175

What to Look For:

• Missing audit logs — No logging of authentication events, access to sensitive data, or security-critical actions
• Insufficient log detail — Logs don’t include enough context (who, what, when, where)
• Sensitive data in logs — Passwords, tokens, PII logged in plaintext
• No log protection — Logs stored without integrity checks, accessible to attackers
• Missing monitoring — No alerting on suspicious activity, no SIEM integration
• Log injection — Attackers can forge or tamper with log entries
• No incident response — No documented procedures for security incidents

Testing Approach:

1. Review what events are logged (authentication, authorization, data access)
2. Check log format and content for sufficiency
3. Search for sensitive data in log statements
4. Verify log storage security and retention
5. Assess monitoring and alerting capabilities

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A10: Server-Side Request Forgery (SSRF)

CWE-918

What to Look For:

• Unvalidated URL parameters — User-supplied URLs fetched by the server without validation
• Internal service access — Can attacker reach internal services (metadata endpoints, admin panels, databases)?
• Cloud metadata endpoints — Access to 169.254.169.254 (AWS, Azure, GCP metadata services)
• File protocol access — Can file:// URLs be used to read local files?
• Redirect following — Server follows redirects to attacker-controlled URLs
• DNS rebinding — Time-of-check vs time-of-use vulnerabilities
• URL parsing inconsistencies — Differences between URL parsers (e.g., @ handling)

Testing Approach:

1. Identify all endpoints accepting URLs from users
2. Test for internal service access (localhost, private IPs)
3. Attempt cloud metadata endpoint access
4. Test alternative protocols (file://, gopher://, dict://)
5. Test for URL parsing bypasses (unicode, encoding, case variations)

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3. Framework-Specific Checks

Apply additional checks based on detected framework:

Framework	Key Security Checks
React/Next.js	XSS via dangerouslySetInnerHTML, SSRF in getServerSideProps, API routes without auth
Angular	XSS protection bypasses, unsafe bypassSecurityTrustHtml, HTTP client interceptors
Vue.js	v-html XSS risks, server-side rendering vulnerabilities
Express.js	Missing Helmet middleware, no rate limiting, prototype pollution
Django	DEBUG=True, SECRET_KEY exposure, raw SQL, CSRF exemptions
Flask	Jinja2 autoescape disabled, unsafe session handling, debug mode
Ruby on Rails	Mass assignment, render with user input, SQL fragments, weak parameters
Spring Boot	SpEL injection, actuator endpoints exposed, mass assignment, CORS issues
Laravel	Mass assignment, raw queries, debug mode, configuration exposure
ASP.NET Core	Razor XSS, insecure deserialization, missing anti-forgery tokens

---

4. Configuration Review

Examine these configuration areas:

Web Server Configuration

• nginx/Apache: Security headers, TLS settings, rate limiting, access controls
• Reverse proxy: Header forwarding, SSL termination, upstream validation
• Load balancer: Health checks, session affinity, DDoS protection

Application Configuration

• Environment-specific settings: Debug mode, error handling, logging levels
• Security settings: Password policies, session timeouts, CSRF protection
• External integrations: API keys, webhook secrets, OAuth configs

Deployment Configuration

• Container security: Non-root user, read-only filesystems, resource limits
• Kubernetes: Network policies, security contexts, RBAC
• Cloud services: IAM roles, security groups, encryption at rest

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5. Produce Findings

For each identified vulnerability:

• Assign severity based on exploitability and impact in deployment context
• Provide concrete evidence (code locations, configuration gaps, test results)
• Propose specific remediation steps with code examples
• Rate confidence (HIGH, MEDIUM, LOW)

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Output Format

## Web Security Review: [Application Name]

### Application Overview
- **Framework**: [React/Express, Django, Rails, etc.]
- **Deployment**: [Internet-facing, internal, cloud platform]
- **Architecture**: [Monolith, microservices, serverless]
- **Authentication**: [Session-based, JWT, OAuth]

### Risk Matrix
| OWASP Ref | Risk | Severity | Status |
|-----------|------|----------|--------|
| A01 | Broken Access Control | HIGH | Finding |
| A02 | Cryptographic Failures | MEDIUM | Finding |
| A03 | Injection | CRITICAL | Finding |
| A04 | Insecure Design | LOW | Finding |
| A05 | Security Misconfiguration | MEDIUM | Finding |
| A06 | Vulnerable Components | HIGH | Finding |
| A07 | Auth Failures | HIGH | Finding |
| A08 | Integrity Failures | N/A | N/A |
| A09 | Logging Failures | MEDIUM | Finding |
| A10 | SSRF | N/A | N/A |

### Findings
[Standard finding template for each identified risk]

### Positive Controls Observed
[Security controls already in place — acknowledge good practices]

### Recommendations
[Prioritized remediation roadmap]

---

OWASP References

• OWASP Top 10 for Web Applications (2021) — owasp.org/Top10
• OWASP ASVS v5.0 — Application Security Verification Standard
• OWASP Testing Guide (WSTG) — Web Security Testing Guide
• OWASP Cheat Sheet Series — Language and framework-specific guidance
• OWASP Proactive Controls — Secure development practices

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