500+ Web Pentesting Interview Questions

500+ Web Pentesting Interview Questions udemy course

Master Web Pentesting Interview with 500+ MCQs with OWASP, Real Scenarios, and Tools – Fast, Practical, Exam-Ready.

Are you preparing for Web Application Pentesting interviews or aiming to sharpen your web security fundamentals? This course is designed specifically to help you master Web Pentesting through a structured, MCQ-based approach that directly aligns with real-world interviews and industry expectations.

The course is tailored for both beginners and intermediate learners who want to:

• Build confidence for web security interviews

• Understand how and why vulnerabilities occur

• Learn mitigation techniques from an attacker’s and defender’s perspective

By the end of this course, you’ll be fully equipped to:

• Tackle time-bound web security MCQs

• Approach real-world web penetration tests

Identify vulnerabilities in authentication, authorization, session management, input validation, and more


This Course was created with Experts.

Interview Topics Included Are :-

I. Fundamentals of Web Application Security

1. Introduction to Web Pentesting

Difficulty: Easy | MCQ Count: 10

Topics:

• Definition of Web Application Penetration Testing (WAPT)

• Difference between Vulnerability Assessment and Penetration Testing

• Phases of a Web Pentest (Reconnaissance, Scanning, Exploitation, Post-Exploitation, Reporting)

• Ethical Hacking vs. Malicious Hacking

• Legal and Ethical Considerations in Pentesting

2. Web Technologies and Protocols

Difficulty: Easy to Medium | MCQ Count: 20

Topics:

• HTTP/HTTPS (methods, headers, status codes)

• TCP/IP (basic understanding)

• DNS (record types, resolution)

• Cookies and Sessions (types, attributes, management)

• Web Servers (Apache, Nginx, IIS - basic functionalities and common configurations)

• Web Proxies (forward, reverse)

• REST APIs and SOAP

• JSON, XML, HTML, JavaScript, CSS

3. OWASP Top 10 (2021 & 2017)

Difficulty: Medium | MCQ Count: 30

Topics:

• Understanding each of the OWASP Top 10 vulnerabilities (detailed explanation, examples, impact, and basic mitigation)

• Changes between OWASP Top 10 2017 and 2021

II. Web Application Vulnerabilities (Deep Dive)

1. Injection Attacks

SQL Injection (SQLi)

Difficulty: Medium to Hard | MCQ Count: 30

Subtopics:

• Types: In-band (Error-based, Union-based), Out-of-band, Blind (Boolean-based, Time-based)

• Techniques: Order By, Group By, Stacking Queries, Second-order SQLi, SQL Truncation

• Bypassing WAFs for SQLi

• Detection and Exploitation Tools (e.g., sqlmap, manual techniques)

• Mitigation Strategies (Parameterized Queries, Stored Procedures, Input Validation, WAFs, ORM)

• Impact and Real-world scenarios

NoSQL Injection

Difficulty: Medium | MCQ Count: 10

Subtopics:

• Understanding NoSQL databases (MongoDB, Cassandra, etc.)

• Injection techniques specific to NoSQL

• Detection and mitigation

Command Injection

Difficulty: Medium | MCQ Count: 10

Subtopics:

• OS Command Injection (e.g., system(), exec())

• Shell Metacharacters and their exploitation

• Blind command injection

• Mitigation (Input validation, proper API usage)

Other Injection Types

Difficulty: Medium | MCQ Count: 15

Subtopics:

• LDAP Injection, XPath Injection, XXE (XML External Entity)

• Understanding the nature of each injection type

• Exploitation examples

• Detection and mitigation

2. Cross-Site Scripting (XSS)

Difficulty: Medium to Hard | MCQ Count: 30

Subtopics:

• Types: Reflected, Stored, DOM-based

• Exploitation Techniques:

  • Bypassing input validation and output encoding

  • Stealing cookies (Session Hijacking)

  • Defacing websites

  • Redirecting users

  • Keylogging

  • Leveraging XSS to achieve RCE (e.g., via AngularJS, client-side template injection)

• XSS in different contexts (HTML, JavaScript, CSS)

• XSS Payloads: Common and advanced payloads

• Mitigation Strategies:

  • Input Validation and Output Encoding (Contextual encoding)

  • Content Security Policy (CSP)

  • HTTPOnly and Secure flags for cookies

  • Client-side frameworks and their XSS protection

3. Broken Access Control

Difficulty: Medium | MCQ Count: 20

Subtopics:

• Insecure Direct Object References (IDOR):

  • Horizontal and Vertical IDOR

  • Bypassing access control checks

  • Detecting IDOR

• Privilege Escalation:

  • Vertical and Horizontal privilege escalation

  • Role-based access control (RBAC) bypasses

• Missing Function Level Access Control:

  • Direct access to admin functions

• Mitigation:

  • Robust authorization checks

  • Principle of Least Privilege

  • Randomized/Hashed IDs for objects

4. Cryptographic Failures

Difficulty: Medium to Hard | MCQ Count: 20

Subtopics:

• Weak Hashing Algorithms (MD5, SHA-1)

• Weak Encryption Algorithms (DES, insecure modes of operation)

• Improper Key Management (hardcoded keys, default keys)

• Sensitive Data Exposure (data in transit, data at rest)

• SSL/TLS Misconfigurations (weak ciphers, expired certificates, mixed content)

• Padding Oracle Attacks

5. Security Misconfiguration

Difficulty: Medium | MCQ Count: 15

Subtopics:

• Default credentials

• Unpatched systems and outdated software

• Directory Listing

• Improper error handling (revealing sensitive information)

• Unnecessary services/ports

• Misconfigured HTTP headers (missing security headers)

• Cloud misconfigurations relevant to web apps (S3 bucket misconfigurations, IAM roles)

6. Vulnerable and Outdated Components

Difficulty: Medium | MCQ Count: 10

Subtopics:

• Understanding the risk of outdated libraries, frameworks, and CMS

• Tools for identifying vulnerable components (e.g., retire.js, dependency-check)

• Software Composition Analysis (SCA)

• Supply chain attacks (e.g., Log4j)

7. Identification and Authentication Failures

Difficulty: Medium to Hard | MCQ Count: 25

Subtopics:

• Weak Password Policies

• Brute-force attacks and Dictionary attacks

• Credential Stuffing

• Session Management issues (fixed session IDs, insecure session regeneration)

• MFA bypass techniques

• Password Reset vulnerabilities

• Single Sign-On (SSO) vulnerabilities (OAuth, SAML)

8. Software and Data Integrity Failures

Difficulty: Medium to Hard | MCQ Count: 15

Subtopics:

• Insecure Deserialization

• Client-side validation bypass

• Software updates and CI/CD pipeline integrity

9. Security Logging and Monitoring Failures

Difficulty: Medium | MCQ Count: 10

Subtopics:

• Lack of proper logging for security events

• Insufficient monitoring and alerting

• Detecting common web attacks through logs

10. Server-Side Request Forgery (SSRF)

Difficulty: Hard | MCQ Count: 15

Subtopics:

• How SSRF works (making arbitrary requests from the server)

• Impact: accessing internal services, cloud metadata APIs, bypassing firewalls

• Blind SSRF

• SSRF bypass techniques

• Mitigation strategies (whitelisting, input validation, network segmentation)

III. Other Critical Web Vulnerabilities

1. Cross-Site Request Forgery (CSRF)

Difficulty: Medium | MCQ Count: 15

Subtopics:

• How CSRF works (tricking authenticated users)

• Impact: unauthorized actions, money transfers

• Distinction from XSS

• CSRF tokens (implementation and bypasses)

• SameSite cookie attribute

2. Business Logic Flaws

Difficulty: Hard | MCQ Count: 10

Subtopics:

• Understanding the application's business logic

• Examples: price manipulation, bypassing workflow, unauthorized discounts, race conditions

• Methodology for finding business logic flaws

3. File Upload Vulnerabilities

Difficulty: Medium | MCQ Count: 10

Subtopics:

• Unrestricted File Upload

• Bypassing file type checks (MIME type, magic bytes)

• Shell upload, webshells

• Path traversal in file uploads

• Mitigation: proper validation, sanitization, renaming, storage outside web root

4. HTTP Host Header Attacks

Difficulty: Hard | MCQ Count: 5

Subtopics:

• Password Reset Poisoning

• Web Cache Deception

• Classic Server-Side Attacks

5. Clickjacking

Difficulty: Medium | MCQ Count: 5

Subtopics:

• How clickjacking works (UI redressing)

• Impact: unauthorized clicks, data exposure

• Mitigation: X-Frame-Options, Content Security Policy (CSP) frame-ancestors directive

6. Open Redirects

Difficulty: Easy | MCQ Count: 5

Subtopics:

• Exploitation: phishing, bypassing security checks

• Detection and mitigation

7. SSRF (Advanced)

Difficulty: Expert | MCQ Count: 5

Subtopics:

• Advanced bypasses for SSRF filters

• SSRF with URL schemes (file://, dict://, gopher://)

• Interacting with internal services (e.g., redis, elasticsearch)

IV. Tools and Methodologies

1. Penetration Testing Methodologies

Difficulty: Easy to Medium | MCQ Count: 10

Topics:

• OSSTMM (Open Source Security Testing Methodology Manual)

• OWASP Web Security Testing Guide (WSTG)

• PTES (Penetration Testing Execution Standard)

• Black Box, White Box, Gray Box Testing

2. Reconnaissance Tools & Techniques

Difficulty: Medium | MCQ Count: 15

Topics:

• Information Gathering (Google Dorking, Shodan, Censys)

• Subdomain Enumeration (DNSDumpster, Amass, Subfinder)

• Port Scanning (Nmap, Masscan - specifically for web ports)

• Directory and File Enumeration (DirBuster, Gobuster, Ffuf)

• Technology Identification (Wappalyzer, BuiltWith)

3. Web Proxy Tools

Burp Suite (Community/Professional)

Difficulty: Medium to Hard | MCQ Count: 25

Topics:

• Proxy functionality (intercepting, modifying requests/responses)

• Repeater, Intruder, Scanner, Sequencer, Decoder, Comparer

• Extensibility (BApp Store)

• Session handling rules

• Macros

• Spidering and crawling

OWASP ZAP

Difficulty: Medium | MCQ Count: 10

Topics:

• Similar functionalities to Burp Suite

• Automated scanning, Fuzzing

• Passive and Active Scan

• Add-ons

4. Other Essential Web Pentesting Tools

Difficulty: Medium | MCQ Count: 20

Topics:

• SQLMap: Automated SQL Injection tool (deep understanding of options and usage)

• Nikto/Wapiti: Web server/application scanners

• Metasploit (Web Modules): Using modules for web exploitation

• Curl/Wget: Command-line web interaction

• Browser Developer Tools: Inspecting elements, network traffic, debugging JavaScript

• Text Editors/IDEs: For code review (if white-box)

V. Advanced Concepts and Specialized Testing

1. API Security Testing

Difficulty: Hard | MCQ Count: 20

Subtopics:

• REST API vulnerabilities (Broken authentication, Injection, BOLA, Mass Assignment)

• GraphQL security (Introspection, Batching attacks)

• SOAP API vulnerabilities (XXE, SQLi)

• API testing methodologies (OWASP API Security Top 10)

• Tools for API testing (Postman, SoapUI, Burp Suite, ZAP)

2. Cloud Security for Web Applications

Difficulty: Hard | MCQ Count: 15

Subtopics:

• Common cloud service providers (AWS, Azure, GCP)

• Shared Responsibility Model

• Cloud-specific web application vulnerabilities (S3 misconfigurations, EC2 vulnerabilities, Lambda function security)

• Serverless application security

3. Container Security for Web Applications

Difficulty: Hard | MCQ Count: 10

Subtopics:

• Docker and Kubernetes security considerations

• Image vulnerabilities

• Container runtime security

4. Source Code Review (White Box Testing)

Difficulty: Hard | MCQ Count: 10

Subtopics:

• Identifying common vulnerability patterns in code (e.g., unsanitized input, insecure API calls)

• Understanding secure coding principles

• SAST (Static Application Security Testing) tools

5. Web Application Firewalls (WAFs)

Difficulty: Hard | MCQ Count: 10

Subtopics:

• Purpose and limitations of WAFs

• WAF bypass techniques for common vulnerabilities (SQLi, XSS)

6. Advanced Exploitation Techniques

Difficulty: Expert | MCQ Count: 20

Subtopics:

• Race Conditions (Time-of-Check to Time-of-Use)

• Deserialization Vulnerabilities

• Template Injection (SSTI, CSTI)

• Prototype Pollution

• Exploiting insecure JWT implementations

7. Secure Software Development Lifecycle (SSDLC)

Difficulty: Medium | MCQ Count: 10

Subtopics:

• Integrating security into development phases (design, development, testing, deployment)

• Threat Modeling (STRIDE, DREAD)

• Security Champions

• DevSecOps principles

8. Reporting and Communication

Difficulty: Easy | MCQ Count: 5

Subtopics:

• Structure of a penetration test report

• Prioritizing vulnerabilities (CVSS, risk rating)

• Clear and concise remediation recommendations

• Communication with developers and stakeholders

• Post-remediation testing

VI. Scenario-Based Questions and Problem Solving

Difficulty: Hard to Expert | MCQ Count: 50

Example Scenarios:

• "You've identified a reflected XSS vulnerability. How would you escalate this to a session hijack?"

• "You suspect a blind SQL injection. Walk me through your testing methodology."

• "The application uses JWTs. What security concerns would you look for?"

• "You found an IDOR. How do you quantify its impact?"

• "Describe how you would approach testing a payment gateway integration."

• "How would you bypass a WAF protecting against SQLi?"

• "A client wants to test their new API. What's your approach?"

VII. General Cybersecurity Concepts

1. Cryptography Basics

Difficulty: Easy to Medium | MCQ Count: 10

Topics:

• Symmetric vs. Asymmetric Encryption

• Hashing vs. Encryption vs. Encoding

• Digital Signatures

• Certificates and PKI

2. Network Security Fundamentals

Difficulty: Easy | MCQ Count: 5

Topics:

• Firewalls (basic understanding, WAF vs. Network Firewall)

• Intrusion Detection/Prevention Systems (IDS/IPS)

• VPNs

3. Secure Coding Principles

Difficulty: Medium | MCQ Count: 10

Topics:

• Input Validation and Output Encoding

• Secure Configuration Management

• Error Handling

• Least Privilege

• Defense in Depth

Summary

Total Estimated MCQ Count: ~485

This comprehensive study guide provides a solid framework for preparing for a deep-dive Web Penetration Testing interview. Remember to not only know the definitions but also understand the "how" and "why" behind each vulnerability and mitigation. Practical experience with the tools and demonstrating problem-solving skills are crucial for success.