Certainly, let’s expand the web penetration testing process with more detailed steps and tools for a comprehensive assessment.

1. Reconnaissance and Information Gathering:

a. Subdomain Enumeration with Sublist3r:

sublist3r -d example.com

b. Technology Stack Enumeration with Wappalyzer or BuiltWith:

Leverage browser extensions or online tools to identify the technologies used in the web application.

c. WHOIS Information Gathering with whois:

whois example.com

2. Network Scanning and Enumeration:

a. Network Discovery with nmap:

nmap -p- -sV -A example.com

b. Service Version Detection with BannerGrab:

bannergrab -p 80 example.com

3. Vulnerability Scanning and Assessment:

a. OWASP ZAP Automated Scanning:

Use OWASP ZAP to perform automated scans for common vulnerabilities.

zap.sh -cmd -quickurl http://example.com

b. Manual SSL/TLS Assessment with sslscan:

sslscan example.com

4. Web Application Mapping and Crawling:

a. Site Map Generation with Burp Suite:

Utilize Burp Suite’s site map to thoroughly map the application’s structure.

b. Content Discovery with gobuster:

gobuster dir -u http://example.com -w /path/to/wordlist.txt -x php,html

FUZZ https://github.com/googleprojectzero/domato

5. Authentication and Session Management:

a. Session Token Analysis with Burp Suite:

Analyze how session tokens are generated and managed during authentication.

b. Password Policy Testing with Hydra and Patator:

hydra -l username -P /path/to/passwords.txt http-post-form "http://example.com/login:username=^USER^&password=^PASS^:Invalid credentials"

6. Cross-Site Scripting (XSS) and Cross-Site Request Forgery (CSRF) Testing:

a. Advanced XSS Payload Testing with XSStrike:

python xsstrike.py -u http://example.com/page

b. CSRF Token Analysis with Burp Suite:

Inspect how CSRF tokens are generated and validate their effectiveness.

7. File Upload Vulnerability Testing:

a. File Upload Exploitation with Metasploit:

Leverage Metasploit modules to test the security of file upload functionalities.

8. API Security Testing:

a. API Security Assessment with OWASP API Security Project:

Follow OWASP API Security Project guidelines for testing API security.

b. Swagger/OpenAPI Enumeration with swagger-ui or swagger-codegen:

Explore API documentation for potential security issues.

9. Web Server and CMS Specific Tests:

a. CMS Security Scanning with Nikto:

nikto -h http://example.com

b. WebDAV Testing with Davtest:

davtest -url http://example.com/webdav/

10. Business Logic and Workflow Testing:

a. User Role Testing:

Explore different user roles and test the application’s access control mechanisms.

b. Business Logic Vulnerability Testing:

Identify and test for vulnerabilities related to the application’s business logic.

11. Mobile Application Testing:

a. Mobile App Traffic Analysis with mitmproxy:

Analyze mobile app traffic for potential vulnerabilities.

b. Reverse Engineering with apktool and dex2jar:

apktool d app.apk -o output_folder
d2j-dex2jar output_folder/classes.dex

12. Reporting and Documentation:

a. Vulnerability Exploitation Proof-of-Concept (PoC):

Include detailed PoCs for identified vulnerabilities.

b. Risk Assessment and Impact Analysis:

Provide a comprehensive risk assessment and impact analysis for each identified vulnerability.

13. Post-Exploitation Testing (if authorized):

a. Privilege Escalation Attempts:

Test for privilege escalation vulnerabilities, especially if the application involves user roles.

b. Data Exfiltration Attempts:

Simulate data exfiltration attempts to validate data protection mechanisms.

14. Client-Side Security Testing:

a. JavaScript Code Analysis with eslint or jslint:

Analyze client-side JavaScript code for security vulnerabilities.

b. HTML and CSS Analysis:

Inspect the security of HTML and CSS code for potential risks.

15. Web Security Headers Analysis:

a. CSP and HSTS Analysis with securityheaders.io:

Check for the presence and effectiveness of Content Security Policy (CSP) and HTTP Strict Transport Security (HSTS) headers.

https://github.com/juerkkil/securityheaders

b. Header Analysis with Nikto:

nikto -h http://example.com

Conclusion:

Web penetration testing is a dynamic and iterative process. It involves a combination of automated tools, manual testing, and creative thinking to uncover vulnerabilities. Regular updates on security trends, continuous learning, and adherence to ethical hacking practices are vital for a successful web penetration testing career.