Web Application Attack Vectors 2025
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Web Application Attack Vectors 2025

About the Book

The landscape of web application security is evolving at breakneck speed. Standard vulnerabilities persist, but modern architectures—microservices, SPAs, serverless functions, and cloud-native deployments—introduce intricate new attack surfaces. "Web Application Attack Vectors 2025" moves decisively beyond introductory concepts, providing an advanced, practical exploration of the sophisticated techniques used to compromise today's complex web applications.

This book dissects cutting-edge attack vectors, revisiting foundational flaws like injection and XSS through an advanced lens while diving deep into contemporary threats targeting APIs (REST, GraphQL, gRPC), complex authentication mechanisms (JWT, SAML, OAuth, MFA), cloud infrastructure, and elusive logic flaws. Explore the nuances of advanced SSRF, deserialization across multiple languages, prototype pollution, request smuggling, cache poisoning, and advanced WAF evasion tactics.

Authored for intermediate-to-advanced penetration testers, security researchers, application security engineers, and experienced developers, this guide equips you with the knowledge to identify, exploit (ethically), and ultimately defend against the evolving threats of 2025 and beyond. Sharpen your skills and stay ahead in the intricate dance between attacker and defender.

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About the Author

Steve T.
Steve T.

Steve T. is a veteran cybersecurity professional with 18 years of deep, hands-on experience in the trenches of digital defense and offense. His extensive career has focused on understanding and mitigating the complex threats targeting web applications and infrastructure. In "Web Application Attack Vectors 2025," Steve distills nearly two decades of practical knowledge into actionable insights, guiding readers through the sophisticated techniques used by modern attackers against today's intricate web environments.

Table of Contents

      • Table of Contents
      • Foreword
      • Preface
      • Who This Book Is For
      • Prerequisites
      • Ethical Considerations and Legal Disclaimer
      • How This Book Is Structured
      • Chapter 1: Beyond the Basics - Revisiting the Foundations with an Advanced Lens
      • 1.1 Advanced Reconnaissance and Information Gathering
      • 1.1.1 OSINT for Web Targets (Subdomain Enumeration, Tech Stack Fingerprinting, Dev/Secret Leakage)
      • 1.1.2 Active Probing Techniques (Advanced Port Scanning, Service Versioning, WAF Detection/Fingerprinting)
      • 1.1.3 JavaScript Source Code Analysis (Endpoint Discovery, Logic Flaws, Secret Exposure)
      • 1.1.4 API Discovery and Mapping (Swagger/OpenAPI, GraphQL Introspection, Traffic Analysis)
      • 1.2 Understanding Modern Web Architectures
      • 1.2.1 Single Page Applications (SPAs) and Client-Side Routing
      • 1.2.2 Microservices and API Gateways
      • 1.2.3 Serverless Functions (FaaS)
      • 1.2.4 Content Delivery Networks (CDNs) and Edge Computing
      • 1.3 Advanced Proxy Usage and Configuration (Burp Suite/OWASP ZAP)
      • 1.3.1 Custom Scripting (Macros, Extenders, Python/Ruby Integration)
      • 1.3.2 Advanced Scoping and Target Definition
      • 1.3.3 Collaboration Features and Project Management
      • Chapter 2: Deep Dive into Injection Vulnerabilities
      • 2.1 SQL Injection: Advanced Exploitation
      • 2.1.1 Second-Order SQL Injection
      • Definition and Concept:
      • Mechanism Breakdown:
      • Example Scenario: User Profile Update and Display
      • Detection Challenges:
      • Exploitation Techniques:
      • Mitigation:
      • 2.1.2 Advanced Blind SQLi Techniques (Time-Based, Error-Based, Boolean-Based Optimization)
      • Boolean-Based Blind SQLi: Optimization Strategies
      • Time-Based Blind SQLi: Handling Instability and Optimizing
      • Error-Based Blind SQLi: Leveraging Conditional Errors
      • Combining Techniques and Tooling:
      • Mitigation Reminder:
      • 2.1.3 Out-of-Band (OOB) SQL Injection
      • Prerequisites:
      • Mechanism:
      • Techniques by Database System:
      • Data Exfiltration Formatting:
      • Challenges and Considerations:
      • Tooling:
      • Mitigation:
      • 2.1.4 Exploiting Specific Database Features
      • PostgreSQL Specific Features:
      • Microsoft SQL Server (MSSQL) Specific Features:
      • Oracle Specific Features:
      • MySQL/MariaDB Specific Features:
      • Mitigation:
      • 2.1.5 WAF Bypass Techniques for SQLi
      • Common WAF Detection Mechanisms for SQLi:
      • Bypass Techniques:
      • Methodology and Tooling:
      • Conclusion on WAF Bypass:
      • 2.2 NoSQL Injection
      • Key Differences from SQL Injection:
      • 2.2.1 Identifying NoSQL Databases
      • 2.2.2 Syntax Differences and Attack Vectors
      • Example Scenario (MongoDB Focus):
      • Attack Vector 1: Bypassing Authentication via Operator Injection
      • Attack Vector 2: Injecting via URL Parameters (if applicable)
      • 2.2.3 Exploiting Operator Injection ($where, $regex, $ne, etc.)
      • 2.2.4 Server-Side JavaScript Injection via NoSQL
      • Mitigation Strategies:
      • 2.3 Server-Side Template Injection (SSTI)
      • Core Concept:
      • Example Scenario (Python/Flask/Jinja2):
      • 2.3.1 Identifying Templating Engines
      • 2.3.2 Context Escapes and Sandbox Bypasses
      • 2.3.3 Crafting Payloads for RCE
      • Payload Example (Common Jinja2 RCE):
      • 2.3.4 Exploiting Blind SSTI
      • Mitigation:
      • 2.4 XML External Entity (XXE) Injection
      • XML Fundamentals: DTDs and Entities
      • The Vulnerability:
      • 2.4.1 Classic XXE for File Disclosure
      • Common File Paths to Target:
      • 2.4.2 XXE for Server-Side Request Forgery (SSRF)
      • 2.4.3 Out-of-Band XXE (OOB-XXE)
      • 2.4.4 Billion Laughs Attack (XML Bomb / DoS)
      • 2.4.5 Exploiting Blind XXE (Error-Based)
      • 2.4.6 Content-Type and Parser Specific Exploitation
      • Mitigation (Crucial):
      • 2.5 OS Command Injection: Advanced Contexts
      • Recap of Basic Command Injection:
      • Advanced Contexts and Injection Points:
      • 2.5.1 Bypassing Filters (Whitespace, Blacklisted Characters, Globbing)
      • 2.5.2 Blind OS Command Injection
      • 2.5.3 Exploiting Context-Specific Injection Points (ImageMagick, FFmpeg, etc.)
      • Mitigation:
      • Chapter 3: Authentication and Authorization Bypass Techniques
      • 3.1 JSON Web Token (JWT) Attacks
      • JWT Structure:
      • 3.1.1 Signature Attacks (alg=none, Key Confusion, Null Signature)
      • 3.1.2 Weak Secret Brute-Forcing
      • Mechanism:
      • Tools for Brute-Forcing:
      • Factors Affecting Success:
      • Impact:
      • Mitigation:
      • 3.1.3 Header Parameter Injection (kid, jku, x5u)
      • The Vulnerability:
      • jku (JWK Set URL) Attack:
      • x5u (X.509 URL) Attack:
      • kid (Key ID) Path Traversal / SQL Injection Attack:
      • General Best Practices:
      • 3.1.4 Replay Attacks and Timing Issues
      • Replay Attacks:
      • Timing Issues (exp, nbf, iat):
      • Mitigation Strategies for Replay and Timing Issues:
      • 3.2 SAML Attacks
      • SAML Flow Overview (SP-Initiated SSO):
      • SAML Structure (XML):
      • 3.2.1 Signature Wrapping (XML Signature Wrapping - XSW)
      • 3.2.2 Assertion Manipulation (Modifying Attributes, Validity Period)
      • 3.2.3 Cross-Site Scripting (XSS) via SAML Responses
      • 3.3 OAuth 2.0 and OpenID Connect Flaws
      • Key Actors in OAuth 2.0 / OIDC:
      • OAuth 2.0 Grant Types (Flows):
      • 3.3.1 Implicit Grant Flow Issues
      • 3.3.2 Redirect URI Validation Bypass
      • 3.3.3 State Parameter Fixation/Hijacking
      • 3.3.4 Scope Misconfiguration and Privilege Escalation
      • 3.3.5 Client Secret Leakage and Consequences
      • 3.4 Multi-Factor Authentication (MFA) Bypass Strategies
      • 3.4.1 Exploiting Weak Recovery Mechanisms
      • 3.4.2 Rate Limiting and Brute-Force on OTPs
      • 3.4.3 Bypassing MFA During Initial Login Flow
      • 3.4.4 Session Token Reuse After MFA
      • 3.4.5 Social Engineering and Factor Compromise
      • 3.5 Complex Access Control Vulnerabilities
      • 3.5.1 Horizontal and Vertical Privilege Escalation via Parameter Manipulation
      • 3.5.2 Exploiting State Machines and Workflow Logic Flaws
      • 3.5.3 HTTP Method Tampering for Authz Bypass
      • 3.5.4 Insecure Direct Object References (IDOR) in Complex Systems (GUIDs, Hashed IDs)
      • Overall Mitigation Strategy for Access Control:
      • Chapter 4: Exploiting Complex Client-Side Vulnerabilities
      • 4.1 Advanced Cross-Site Scripting (XSS)
      • 4.1.1 DOM-Based XSS Deep Dive (Sources, Sinks, Taint Tracking)
      • 4.1.2 Mutation XSS (mXSS)
      • The Problem: Sanitization vs. Browser Parsing Quirks
      • Example Scenario (Conceptual):
      • Key Characteristics of mXSS:
      • Discovering mXSS:
      • Impact:
      • Mitigation:
      • 4.1.3 XSS in Uncommon Contexts (SVG, MathML, Service Workers, WebSockets)
      • 1. XSS within SVG (Scalable Vector Graphics)
      • 2. XSS within MathML (Mathematical Markup Language)
      • 3. XSS via Service Workers
      • 4. XSS via WebSockets
      • General Principle:
      • 4.1.4 Bypassing Content Security Policy (CSP)
      • Understanding CSP Directives:
      • Common Source Values:
      • CSP Bypass Techniques:
      • Developing Secure CSPs:
      • 4.1.5 Exploiting PostMessage Vulnerabilities
      • How postMessage Works:
      • Vulnerabilities in postMessage Implementation:
      • Finding postMessage Vulnerabilities:
      • 4.1.6 Universal XSS (UXSS) and Browser-Level Flaws (Conceptual)
      • Key Differences from Standard XSS:
      • Root Causes and Conceptual Examples:
      • Impact:
      • Mitigation and Responsibility:
      • Conclusion on UXSS:
      • 4.2 JavaScript Prototype Pollution
      • Understanding Prototypes in JavaScript:
      • The Vulnerability:
      • 4.2.1 Identifying Vulnerable Code Patterns
      • 4.2.2 Client-Side Exploitation
      • Finding Gadgets:
      • 4.2.3 Server-Side Exploitation (Context)
      • Mitigation:
      • 4.3 DOM Clobbering
      • The Mechanism: Named Access on window and document
      • The Vulnerability:
      • Example Scenario:
      • Key Clobbering Patterns and Targets:
      • 4.3.1 Overwriting Global Variables and Functions
      • 4.3.2 Bypassing Security Checks (DOMPurify, etc.)
      • 4.3.3 Chaining with Other Vulnerabilities
      • Mitigation:
      • 4.4 Advanced Cross-Site Request Forgery (CSRF)
      • Classic CSRF Recap:
      • 4.4.1 CSRF against JSON Endpoints
      • 4.4.2 Bypassing Referer Checks and Origin Headers
      • 4.4.3 Login/Logout CSRF Attacks
      • 4.4.4 Exploiting CSRF in APIs without Standard Browser Protections
      • General CSRF Best Practices:
      • 4.5 Clickjacking and UI Redressing: Advanced Techniques
      • Classic Clickjacking Recap:
      • 4.5.1 Bypassing Frame-Busting Scripts
      • 4.5.2 Drag-and-Drop Attacks
      • 4.5.3 Exploiting Nested Contexts and Partial Overlays
      • 4.5.4 Content Security Policy frame-ancestors Bypass (Misconfigurations)
      • Mitigation:
      • Conclusion on Clickjacking:
      • Chapter 5: Server-Side Request Forgery (SSRF) - In Depth
      • 5.1 Identifying SSRF Vulnerabilities
      • 5.1.1 Explicit SSRF (URL Parameters)
      • 5.1.2 Blind SSRF (No Direct Response)
      • 5.1.3 SSRF via Uncommon Protocols (gopher://, dict://, file://)
      • SSRF via Data Formats and Headers:
      • 5.2 Exploitation Techniques
      • 5.2.1 Internal Network Scanning and Port Enumeration
      • 5.2.2 Interacting with Internal Services
      • 5.2.3 Reading Local Files (file:// wrapper)
      • 5.2.4 Cloud Instance Metadata Abuse
      • 5.2.5 Chaining SSRF with Other Vulnerabilities
      • 5.3 Bypassing SSRF Filters
      • Common Filtering Strategies:
      • Bypass Techniques:
      • Testing Bypass Techniques:
      • Mitigation (Building Robust Filters):
      • Chapter 6: Deserialization Vulnerabilities
      • 6.1 Understanding Serialization and Deserialization
      • 6.1.1 Common Formats
      • 6.1.2 The Concept of Gadget Chains
      • 6.2 Java Deserialization Attacks
      • 6.2.1 Identifying Vulnerable Libraries (e.g., Apache Commons Collections)
      • Identifying Vulnerable Applications:
      • 6.2.2 Using Tools like ysoserial
      • 6.2.3 Exploiting Custom Serializable Objects
      • 6.2.4 Targeting RMI, JMX, JMS Endpoints
      • Mitigation Strategies for Java Deserialization:
      • 6.3 PHP Deserialization (Object Injection)
      • 6.3.1 Identifying unserialize() Usage
      • PHP Serialized Format Recap:
      • 6.3.2 Finding POP (Property Oriented Programming) Gadgets
      • 6.3.3 Exploiting Phar Deserialization (phar:// wrapper)
      • Mitigation for General PHP Deserialization:
      • 6.4 Python Deserialization (Pickle)
      • 6.4.1 The pickle Module Dangers
      • Python Pickle Format (Conceptual):
      • Identifying Vulnerable Code:
      • 6.4.2 Crafting Malicious Pickle Payloads (__reduce__)
      • Mitigation (Crucial):
      • 6.5 .NET Deserialization
      • 6.5.1 Targeting BinaryFormatter, LosFormatter, JSON.NET, XmlSerializer
      • 6.5.2 Using Tools like ysoserial.net
      • Mitigation Strategies for .NET Deserialization:
      • 6.6 Blind Deserialization and Mitigation Bypass
      • Blind Deserialization Exploitation:
      • Mitigation Bypass Techniques:
      • Conclusion on Blind Exploitation and Bypasses:
      • Chapter 7: Attacking APIs and Microservices
      • 7.1 REST API Security Testing
      • 7.1.1 Authentication/Authorization Flaws (API Keys, JWT, OAuth)
      • 7.1.2 Rate Limiting and Resource Exhaustion
      • 7.1.3 Mass Assignment Vulnerabilities
      • 7.1.4 Injection Vulnerabilities in API Parameters
      • 7.1.5 SSRF via API Endpoints
      • 7.2 GraphQL Security Testing
      • GraphQL Fundamentals:
      • 7.2.1 Introspection Query Abuse
      • 7.2.2 Denial of Service via Deeply Nested/Complex Queries
      • 7.2.3 Authorization Bypass in Resolvers
      • 7.2.4 Batching Attack Amplification
      • 7.2.5 Injection within GraphQL Arguments
      • 7.3 Attacking gRPC and Protocol Buffers
      • gRPC Fundamentals:
      • 7.3.1 Service Discovery and Method Enumeration
      • 7.3.2 Manipulating Protobuf Payloads
      • 7.3.3 Authentication and Authorization Issues
      • 7.3.4 Exploiting Server Reflection
      • 7.3.5 Denial of Service
      • 7.3.6 Traditional Injection (via Protobuf Data)
      • Mitigation Strategies Specific to gRPC:
      • 7.4 API Gateway and Service Mesh Security Issues
      • 7.4.1 Misconfigurations in Routing and Authentication (API Gateways / Ingress)
      • 7.4.2 Bypassing Security Policies at the Gateway
      • 7.4.3 Service Mesh Security Issues (e.g., Istio, Linkerd)
      • Testing and Mitigation Strategies:
      • Chapter 8: Exploiting Business Logic Flaws
      • 8.1 Identifying Logic Flaws
      • 8.1.1 Understanding Application Workflows
      • 8.1.2 Threat Modeling Business Processes
      • 8.1.3 Looking for Assumptions and Edge Cases
      • 8.2 Common Patterns
      • 8.2.1 Parameter Tampering for Unauthorized Actions
      • 8.2.2 Exploiting Weak Validation Logic
      • 8.2.3 Circumventing Multi-Step Processes
      • 8.2.4 Price Manipulation and Discount Abuse (Revisited)
      • 8.2.5 Feature Abuse
      • Mitigation for Business Logic Flaws:
      • 8.3 Race Conditions
      • 8.3.1 Identifying Potential Race Conditions (TOCTOU - Time-of-Check to Time-of-Use)
      • 8.3.2 Exploitation Techniques
      • 8.3.3 Tools and Techniques for Triggering Race Conditions
      • Mitigation Strategies:
      • Chapter 9: Web Cache Poisoning and Deception
      • 9.1 Understanding Web Caching Mechanisms
      • 9.2 Cache Poisoning Techniques
      • 9.2.1 Exploiting Unkeyed Inputs (Headers, Cookies)
      • 9.2.2 HTTP Request Smuggling for Cache Poisoning
      • 9.2.3 Chaining with XSS or Open Redirects
      • Mitigation for Cache Poisoning:
      • 9.3 Cache Deception Attacks
      • Mitigation for Cache Deception:
      • 9.4 Edge Side Includes (ESI) Injection
      • 9.4.1 Identifying ESI Usage:
      • 9.4.2 Exploiting ESI for SSRF and XSS:
      • Chapter 10: HTTP Request Smuggling
      • 10.1 Understanding Ambiguous Requests (CL.TE, TE.CL, TE.TE)
      • 10.1.1 CL.TE: Front-End uses Content-Length, Back-End uses Transfer-Encoding
      • 10.1.2 TE.CL: Front-End uses Transfer-Encoding, Back-End uses Content-Length
      • 10.1.3 TE.TE: Front-End and Back-End both use Transfer-Encoding, but one can be Downgraded/Obfuscated
      • 10.2 Identifying Request Smuggling Vulnerabilities
      • 10.3 Exploitation Techniques
      • 10.3.1 Bypassing Front-End Security Controls
      • 10.3.2 Session Hijacking / Request Hijacking
      • 10.3.3 Web Cache Poisoning via Request Smuggling
      • 10.3.4 Cross-Site Scripting (XSS) via Smuggled Requests
      • Mitigation:
      • Chapter 11: Cloud-Native Application Security
      • 11.1 Serverless (FaaS) Security Issues
      • 11.2 Container Security (Docker, Kubernetes)
      • 11.3 Cloud Storage Misconfigurations (S3, Azure Blob, GCS)
      • 11.4 Infrastructure as Code (IaC) Security Review
      • Chapter 12: Advanced Evasion Techniques
      • 12.1 Bypassing Web Application Firewalls (WAFs)
      • 12.2 Bypassing Client-Side Controls
      • 12.3 Rate Limit Bypass Techniques
      • Conclusion on Evasion:
      • Chapter 13: Exploit Chaining and Post-Exploitation
      • 13.1 The Art of Chaining Vulnerabilities
      • 13.2 Web-Based Post-Exploitation
      • Conclusion:
      • Chapter 14: Reporting, Remediation, and Future Trends
      • 14.1 Writing High-Quality Technical Reports
      • 14.2 Advanced Remediation Strategies
      • 14.3 Emerging Threats and Future Trends
      • Concluding Thoughts:
      • Appendix A: Tooling Quick Reference
      • Appendix B: Useful Payloads and Cheat Sheets

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