# Penetration Test Scope & Boundaries

**Primary Directive:** This analysis is strictly limited to the **network-accessible attack surface** of the application. All findings reported meet the "In-Scope" criteria defined below.

## In-Scope: Network-Reachable Components
A component is considered **in-scope** if its execution can be initiated, directly or indirectly, by a network request that the deployed application server is capable of receiving. This includes:
- Publicly exposed web pages and API endpoints (4 HTTP endpoints identified)
- Endpoints requiring authentication via the application's JWT cookie mechanism
- Any developer utility, debug console, or script that has been mistakenly exposed through a route

## Out-of-Scope: Locally Executable Only
The following components are **out-of-scope** as they cannot be invoked through the running application's network interface:
- **Makefile** (`/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/Makefile`) - Build automation, requires CLI execution
- **benchmark.json** - CTF metadata file, not network-accessible
- **PhantomJS** - Installed in Docker container but not used by any network-accessible code paths

---

## 1. Executive Summary

This Flask-based web application (XBEN-091-24) is a deliberately vulnerable CTF challenge demonstrating critical JWT authentication bypass vulnerabilities. The application exposes **4 network-accessible HTTP endpoints** on port 5003, with the `/dashboard` endpoint containing the CTF flag accessible only to users with the "admin" role. The application's security posture is **critically compromised** across multiple attack vectors.

**Most Critical Findings:**
1. **JWT Algorithm Confusion Attack (CVSS 9.8)** - Tokens use `algorithm='none'` with completely disabled signature verification, enabling trivial authentication bypass and privilege escalation from regular user to admin
2. **Hardcoded Credentials** - Admin password `AdmAQ#DCFQ` exposed in source code alongside plaintext password storage
3. **Missing Security Headers** - No HSTS, CSP, X-Frame-Options, or other protective headers configured
4. **Insecure Session Management** - Cookies lack HttpOnly, Secure, and SameSite flags, enabling XSS-based token theft and CSRF attacks
5. **No Rate Limiting** - Login endpoint vulnerable to brute force attacks

The primary attack path is JWT token forgery: an attacker can create a token with `{"username": "attacker", "role": "admin"}` without any cryptographic signature, access the `/dashboard` endpoint, and retrieve the flag. The application runs on HTTP-only (no TLS), uses end-of-life dependencies (Python 3.8.17, Debian Buster), and lacks fundamental security controls including CSRF protection, input validation, and audit logging.

**Architecture Overview:** Monolithic Python Flask 3.0.3 application deployed in a Docker container with in-memory user storage (no database), stateless JWT-based authentication, and a single-instance deployment model. The application serves as a security training benchmark specifically testing JWT signature validation vulnerabilities.

---

## 2. Architecture & Technology Stack

### Framework & Language
**Primary Stack:**
- **Language:** Python 3.8.17 (EOL October 2024 - no security updates)
- **Framework:** Flask 3.0.3 (web framework)
- **WSGI Server:** Werkzeug 3.0.3 (development server - NOT production-grade)
- **Template Engine:** Jinja2 3.1.4

**Security Implications:**
- Python 3.8.17 reached end-of-life in October 2024 and no longer receives security patches
- Werkzeug development server is explicitly not recommended for production use and lacks security hardening features like request timeout enforcement, connection limits, and DoS protection
- Running on port 5003 with HTTP-only (no TLS/HTTPS configured)
- Application binds to `0.0.0.0` (all network interfaces), accepting connections from any source

### Architectural Pattern
**Pattern:** Monolithic web application with stateless authentication

**Key Characteristics:**
- Single Flask process handling all requests
- No microservices or service mesh architecture
- No database layer (in-memory user store at lines 9-12 of `app.py`)
- Stateless authentication via JWT tokens stored in cookies
- No external API dependencies
- No background job processing

**Trust Boundaries:**
1. **External ↔ Application Boundary:** HTTP port 5003 accepts unauthenticated requests to `/` and `/login`
2. **Unauthenticated ↔ Authenticated Boundary:** JWT token issuance at `/login` (lines 27-31)
3. **User ↔ Admin Boundary:** Role-based access control at `/dashboard` (lines 63-67) - **CRITICALLY VULNERABLE** due to JWT forgery

**Security Architecture Issues:**
- No defense-in-depth: single authentication mechanism (JWT) is completely broken
- Trust boundary between user and admin roles exists only in client-controlled JWT payload
- No server-side session storage or token revocation mechanism
- Application runs as root in Docker container (no user privilege separation)

### Critical Security Components

**1. Authentication System (CRITICALLY VULNERABLE)**
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 20-35
- **Mechanism:** Form-based login with JWT token issuance
- **Vulnerability:** JWT created with `algorithm='none'` and empty signing key (line 27)
- **Impact:** Complete authentication bypass - tokens can be forged by any attacker

**2. Authorization System (CRITICALLY VULNERABLE)**
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 44, 61
- **Mechanism:** Role-based access control (RBAC) with roles extracted from JWT payload
- **Vulnerability:** `verify_signature: False` disables cryptographic validation
- **Impact:** Privilege escalation from 'user' to 'admin' role via JWT payload manipulation

**3. User Data Store (INSECURE)**
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 9-12
- **Implementation:** In-memory Python dictionary with plaintext passwords
- **Credentials:** User: `user/user`, Admin: `admin/AdmAQ#DCFQ`
- **Vulnerability:** No password hashing, hardcoded credentials, credentials exposed in source control

**4. Session Management (VULNERABLE)**
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` line 30
- **Implementation:** JWT token stored in cookie named 'token'
- **Vulnerabilities:** No HttpOnly flag (XSS can steal tokens), no Secure flag (tokens sent over HTTP), no SameSite flag (CSRF vulnerable)

**5. Secret Management (WEAK)**
- **JWT Secret:** Hardcoded `SECRET_KEY = 'supersecretkey'` at line 14 (not used for signing)
- **Flag Storage:** Environment variable `FLAG` loaded from `.env` file
- **Issue:** JWT signing uses empty string `''` instead of SECRET_KEY, rendering secret key ineffective

**Infrastructure Components:**
- **Base OS:** Debian Buster 10 (EOL June 2022 - no security updates)
- **PhantomJS:** Installed but unused (abandoned project with known CVEs)
- **Docker:** Single-container deployment exposing port 5003
- **Health Check:** HTTP GET to `http://localhost:5003` every 10 seconds

---

## 3. Authentication & Authorization Deep Dive

### Authentication Mechanisms and Security Properties

**Primary Authentication Flow:**
1. User submits credentials via POST to `/login` (lines 23-24)
2. Application performs plaintext password comparison (line 26)
3. Upon success, JWT token is created with user's role (line 27)
4. Token set as HTTP cookie and user redirected to `/profile` (lines 29-31)

**Critical Vulnerability Analysis:**

**JWT Token Generation (Line 27):**
```python
token = jwt.encode({"username": username, "role": users[username]['role']}, '', algorithm='none')
```
- **Algorithm:** Uses `algorithm='none'` which produces unsigned tokens (no HMAC or RSA signature)
- **Secret Key:** Empty string `''` instead of using `SECRET_KEY` variable
- **Payload:** Contains username and role claims, no expiration (`exp`), no issuer (`iss`), no token ID (`jti`)
- **Security Impact:** Any attacker can create a valid-looking JWT with arbitrary username and role values

**JWT Token Validation (Lines 44 & 61):**
```python
payload = jwt.decode(token, options={"verify_signature": False})
```
- **Signature Verification:** Explicitly disabled via `verify_signature: False`
- **Security Impact:** Even if an attacker used a different algorithm or invalid signature, the token would still be accepted
- **Exploitability:** Trivial - attacker can craft token `{"username": "attacker", "role": "admin"}`, base64-encode it, and access admin-only resources

### Complete API Endpoints for Authentication

**Login Endpoint:**
- **Route:** `POST /login`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 20-35
- **Purpose:** Authenticate user and issue JWT token
- **Input:** Form data with `username` and `password` fields
- **Output:** Redirect to `/profile` with JWT token in cookie (success) or 401 JSON response (failure)
- **Vulnerabilities:** No rate limiting, no CSRF protection, plaintext password comparison, no account lockout

**Logout Endpoint:**
- **Status:** ❌ NOT IMPLEMENTED
- **Security Impact:** No way to invalidate tokens, compromised tokens valid indefinitely

**Token Refresh Endpoint:**
- **Status:** ❌ NOT IMPLEMENTED
- **Security Impact:** Tokens never expire (no `exp` claim), cannot be refreshed

**Password Reset Endpoint:**
- **Status:** ❌ NOT IMPLEMENTED
- **Security Impact:** No self-service password recovery mechanism

### Session Management and Token Security

**Session Cookie Configuration (Line 30):**
```python
resp.set_cookie('token', token)
```

**Critical Missing Security Flags:**

| Flag | Status | Current | Recommended | Security Impact |
|------|--------|---------|-------------|-----------------|
| HttpOnly | ❌ NOT SET | Accessible to JavaScript | `httponly=True` | XSS attacks can steal tokens via `document.cookie` |
| Secure | ❌ NOT SET | Sent over HTTP | `secure=True` | Man-in-the-middle attacks can intercept tokens |
| SameSite | ❌ NOT SET | No CSRF protection | `samesite='Strict'` | Cross-site request forgery possible |
| Max-Age | ❌ NOT SET | Session cookie | `max_age=3600` | Tokens persist across browser sessions indefinitely |

**Secure Configuration Example:**
```python
# Should be implemented:
resp.set_cookie('token', token, httponly=True, secure=True, samesite='Strict', max_age=3600)
```

**File and Line for Cookie Flag Configuration:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Line:** 30
- **Current Implementation:** `resp.set_cookie('token', token)` with no security flags

### Authorization Model and Bypass Scenarios

**Authorization Implementation:**

**Role-Based Access Control (RBAC):**
- **Roles:** `user` (limited access) and `admin` (full access including flag retrieval)
- **Role Storage:** JWT payload field `"role"`
- **Role Assignment:** Determined at login based on hardcoded user dictionary (line 27)

**Authorization Check Example (/dashboard endpoint, lines 61-67):**
```python
payload = jwt.decode(token, options={"verify_signature": False})
role = payload['role']
if role == 'admin':
    flag = os.getenv('FLAG', 'No flag found')
    return flag
else:
    return jsonify({"message": "Unauthorized"}), 403
```

**Authorization Bypass Scenarios:**

**Scenario 1: Direct JWT Forgery (Trivial)**
1. Create JWT payload: `{"username": "attacker", "role": "admin"}`
2. Base64-encode payload (no signature needed due to `algorithm='none'`)
3. Set as cookie value for `token`
4. Access `/dashboard` endpoint
5. **Result:** Flag retrieved, authorization completely bypassed

**Scenario 2: Role Modification (Trivial)**
1. Login as legitimate user (`user/user`)
2. Capture JWT token from cookie
3. Decode JWT, change `"role": "user"` to `"role": "admin"`
4. Re-encode JWT (no re-signing needed)
5. Replace cookie value
6. **Result:** Privilege escalation from user to admin

**Scenario 3: Token Replay (No expiration)**
1. Obtain any valid admin token (via forgery or compromise)
2. Use token indefinitely (no expiration validation)
3. **Result:** Persistent unauthorized access

### Multi-tenancy Security Implementation
**Status:** ❌ NOT APPLICABLE - Single-tenant application with no tenant isolation mechanisms

### SSO/OAuth/OIDC Flows
**Status:** ❌ NOT IMPLEMENTED

- No OAuth 2.0, OpenID Connect, or SAML integrations
- No callback endpoints for external identity providers
- No state parameter validation (N/A)
- No nonce parameter validation (N/A)
- Application uses only local username/password authentication

---

## 4. Data Security & Storage

### Database Security

**Database Type:** None - Application uses in-memory data storage only

**User Data Store Implementation:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Lines:** 9-12
- **Structure:** Python dictionary with plaintext credentials

```python
users = {
    "user": {"password": "user", "role": "user"},
    "admin": {"password": "AdmAQ#DCFQ", "role": "admin"}
}
```

**Security Analysis:**
- **No Encryption at Rest:** Passwords stored in plaintext in application memory
- **No Password Hashing:** Direct string comparison for authentication (line 26)
- **Hardcoded Credentials:** User accounts defined in source code, exposed in version control
- **No Access Controls:** Any code within the application can access the `users` dictionary
- **No Query Safety:** Not applicable (no database queries)
- **Data Persistence:** All user data lost on application restart

**Critical Vulnerability:** Admin password `AdmAQ#DCFQ` is exposed in source code at line 11, enabling anyone with repository access to authenticate as admin without exploitation.

### Data Flow Security

**Sensitive Data Paths Identified:**

**1. Credentials Flow (Login Process):**
- **Input:** HTTP POST form data at lines 23-24 (`username`, `password`)
- **Processing:** Plaintext comparison at line 26
- **Storage:** Not stored (compared against hardcoded values)
- **Output:** JWT token issued at line 27, set in cookie at line 30
- **Protection:** ❌ None - transmitted over HTTP, no input validation, no rate limiting

**2. JWT Token Flow:**
- **Creation:** Line 27 with unsigned algorithm
- **Storage:** Client-side cookie (line 30) without security flags
- **Transmission:** HTTP requests (no HTTPS)
- **Validation:** Lines 39, 56 (token retrieval), lines 44, 61 (token decode with disabled verification)
- **Protection:** ❌ None - no signature, no expiration, no revocation

**3. Flag Data Flow (CTF Objective):**
- **Storage:** Environment variable `FLAG` loaded from `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/.env`
- **Retrieval:** Line 64 via `os.getenv('FLAG', 'No flag found')`
- **Access Control:** Role check at line 63 (requires `role == 'admin'`)
- **Output:** Line 65 - direct return as HTTP response body
- **Protection:** ⚠️ Minimal - role-based access control bypassed via JWT forgery

**4. Session Cookie Flow:**
- **Creation:** Line 30 after successful authentication
- **Transmission:** Every request to `/profile` and `/dashboard`
- **Validation:** Cookie retrieval at lines 39, 56
- **Protection:** ❌ None - no HttpOnly (XSS can steal), no Secure (MITM can intercept), no SameSite (CSRF possible)

**Data Protection Mechanisms:**
- **Input Sanitization:** ❌ Not implemented
- **Output Encoding:** Partial (Jinja2 auto-escaping for templates, but `render_template_string` used)
- **Encryption in Transit:** ❌ Not implemented (HTTP only, no TLS)
- **Encryption at Rest:** ❌ Not implemented (plaintext passwords)
- **CSRF Protection:** ❌ Not implemented
- **XSS Protection:** Partial (Jinja2 escaping, but no CSP headers)

### Multi-tenant Data Isolation
**Status:** ❌ NOT APPLICABLE

This is a single-tenant application with no multi-tenancy architecture. There are no tenant boundaries, tenant-specific data segregation, or cross-tenant access controls to assess.

---

## 5. Attack Surface Analysis

### External Entry Points (Network-Accessible)

**All endpoints verified as network-accessible through Docker port mapping 5003:5003 and Flask server binding to 0.0.0.0:5003**

#### Entry Point 1: Root Redirect
- **Route:** `GET /`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 16-18
- **Authentication:** None required
- **Functionality:** Simple redirect to `/login` endpoint
- **Attack Surface:** Minimal - no user input processing
- **Security Concerns:** None (benign redirect)

#### Entry Point 2: Login Form & Authentication Handler
- **Routes:** `GET /login` (form display), `POST /login` (authentication)
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 20-35
- **Authentication:** None required (public endpoint)
- **Functionality:** Renders login form (GET), processes credentials and issues JWT (POST)
- **Input Parameters:** `username` (form field), `password` (form field)
- **Attack Surface:**
  - **Brute Force:** No rate limiting on authentication attempts
  - **CSRF:** No CSRF token protection on form submission
  - **Credential Stuffing:** Known admin password in source code enables direct compromise
  - **Timing Attacks:** Plaintext comparison may leak username validity via timing differences
- **Security Concerns:**
  - User enumeration possible via response time analysis
  - No account lockout mechanism after failed attempts
  - No logging of authentication failures
  - Weak user password (`user`) enables trivial compromise

#### Entry Point 3: User Profile Page
- **Route:** `GET /profile`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 37-52
- **Authentication:** Required (JWT token in cookie)
- **Functionality:** Displays role-based profile content (admin users see hidden dashboard link)
- **Input Parameters:** `token` cookie (JWT)
- **Attack Surface:**
  - **JWT Forgery:** Token signature not verified, enabling unauthorized access
  - **Session Hijacking:** Cookie lacks HttpOnly flag, vulnerable to XSS-based theft
  - **SSTI Potential:** Uses `render_template_string()` - currently safe as templates are hardcoded, but dangerous pattern
- **Security Concerns:**
  - Template strings hardcoded at lines 47 and 49 (currently safe, but risky practice)
  - Hidden link to `/dashboard` disclosed in HTML for admin users (line 47)
  - No token expiration validation

#### Entry Point 4: Admin Dashboard (Flag Retrieval)
- **Route:** `GET /dashboard`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` lines 54-69
- **Authentication:** Required (JWT token with admin role)
- **Functionality:** Returns CTF flag for authorized admin users
- **Input Parameters:** `token` cookie (JWT with role claim)
- **Attack Surface:**
  - **Authorization Bypass:** JWT signature verification disabled, role claim client-controlled
  - **Privilege Escalation:** User role can be changed to admin via JWT modification
  - **Direct Object Reference:** Flag retrieval has no additional verification beyond role check
- **Security Concerns:**
  - Primary CTF objective endpoint - contains flag value
  - Authorization check at line 63 relies entirely on unverified JWT claim
  - Flag returned directly in HTTP response body (line 65)

### Internal Service Communication
**Status:** NOT APPLICABLE - Single monolithic application with no internal service-to-service communication, no microservices architecture, and no inter-process communication mechanisms.

### Input Validation Patterns

**Current Implementation:** Minimal to none across all network-accessible endpoints

**Login Endpoint Input Validation (Lines 23-26):**
```python
username = request.form.get('username')  # No validation
password = request.form.get('password')  # No validation

if username in users and users[username]['password'] == password:
```

**Validation Gaps:**
- ❌ No username format validation (length, character set, special characters)
- ❌ No password complexity requirements
- ❌ No input sanitization before processing
- ❌ No protection against null/empty values (Flask's `get()` returns None if missing)
- ❌ No maximum length enforcement (potential DoS via large payloads)

**JWT Token Input Validation (Lines 39-50, 56-68):**
```python
token = request.cookies.get('token')
if not token:
    return redirect(url_for('login'))

payload = jwt.decode(token, options={"verify_signature": False})
```

**Validation Gaps:**
- ❌ No token format validation
- ❌ No signature verification (explicitly disabled)
- ❌ No expiration validation (no `exp` claim checked)
- ❌ No issuer validation (no `iss` claim)
- ❌ No audience validation (no `aud` claim)
- ⚠️ Basic exception handling for `jwt.InvalidTokenError` (lines 51, 68)

**Form Data Validation:**
- Login form (`/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/templates/login.html`) has no client-side or server-side validation
- No CSRF token validation
- No HTML5 input constraints (no `required`, `minlength`, `maxlength` attributes)

### Background Processing
**Status:** NOT APPLICABLE - Application has no background job processing, no task queues (Celery, RQ, etc.), no asynchronous workers, and no scheduled tasks. All processing occurs synchronously within HTTP request handlers.

---

## 6. Infrastructure & Operational Security

### Secrets Management

**Secret #1: JWT Signing Key**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Line:** 14
- **Value:** `SECRET_KEY = 'supersecretkey'`
- **Security Issues:**
  - Hardcoded in source code
  - Weak, predictable value
  - Exposed in version control history
  - **NOT ACTUALLY USED** - JWT signing uses empty string `''` at line 27
- **Rotation:** No rotation mechanism exists

**Secret #2: Admin Credentials**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Lines:** 10-11
- **Values:** `admin` / `AdmAQ#DCFQ`
- **Security Issues:**
  - Hardcoded in application source
  - Stored in plaintext
  - Committed to version control
  - No password hashing
- **Rotation:** Requires code change and redeployment

**Secret #3: CTF Flag**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/.env`
- **Line:** 1
- **Value:** `FLAG="flag{6933908d-2725-4cfb-864e-62ad793d5017}"`
- **Security Issues:**
  - Environment variable file may be committed to version control (check `.gitignore`)
  - No encryption for flag value
- **Best Practice:** Using environment variables is appropriate, but `.env` file should be excluded from version control

**Dockerfile Secret Handling:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile`
- **Lines:** 21-22
```dockerfile
ARG FLAG
ENV FLAG=$FLAG
```
- **Security Issues:**
  - Build-time ARG values visible in Docker image history (`docker history` command)
  - ENV values visible via `docker inspect` command
  - Runtime environment variables preferable to build-time arguments for secrets

### Configuration Security

**Environment Separation:**
- No evidence of multiple environments (dev, staging, prod)
- Single `.env` file for configuration
- No environment-specific configuration files

**Secret Handling:**
- **Password Storage:** ❌ Plaintext in source code (lines 9-12)
- **JWT Secret:** ❌ Hardcoded and unused (line 14)
- **Flag Storage:** ✅ Environment variable (appropriate method)
- **Secrets Manager:** ❌ Not implemented (no AWS Secrets Manager, HashiCorp Vault, etc.)

**Infrastructure Configuration - Security Headers:**

**Nginx/Reverse Proxy Configuration:**
- **Status:** ❌ NOT DETECTED
- No Nginx, Apache, or reverse proxy configuration files found
- Application directly exposed via Flask development server
- **Missing Headers:** HSTS, X-Frame-Options, X-Content-Type-Options, CSP

**Application-Level Security Headers:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Status:** ❌ NOT CONFIGURED
- No `@app.after_request` decorator for adding security headers
- **Expected Location:** Should be added after line 72 (before `app.run()`)

**Missing Security Headers:**

| Header | Purpose | Risk of Absence |
|--------|---------|----------------|
| `Strict-Transport-Security` (HSTS) | Force HTTPS | MITM attacks, credential interception |
| `X-Frame-Options` | Prevent clickjacking | UI redressing attacks |
| `X-Content-Type-Options: nosniff` | Prevent MIME sniffing | Drive-by downloads |
| `Content-Security-Policy` (CSP) | XSS protection | Script injection attacks |
| `X-XSS-Protection` | Legacy XSS filter | Limited protection in older browsers |
| `Referrer-Policy` | Control referrer info | Information disclosure |
| `Permissions-Policy` | Feature restrictions | Unwanted feature access |
| `Cache-Control` | Prevent sensitive data caching | Credential/token leakage |

**Docker Compose Configuration:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/docker-compose.yml`
- **Port Mapping:** `5003:5003` (HTTP only, no HTTPS)
- **Health Check:** Basic HTTP GET to `http://localhost:5003`
- **Security Issues:** No TLS termination, no network isolation, no resource limits

### External Dependencies

**Third-Party Services:**
- ❌ NONE - Application is fully self-contained with no external API calls, no third-party authentication providers, and no external data sources

**Python Dependencies (from requirements.txt):**

| Package | Version | Purpose | Known Vulnerabilities |
|---------|---------|---------|----------------------|
| Flask | 3.0.3 | Web framework | Current stable version |
| PyJWT | 2.10.1 | JWT handling | **Misconfigured** (algorithm='none' vulnerability is implementation issue) |
| cryptography | 42.0.7 | Crypto operations | Installed but **UNUSED** in application code |
| Werkzeug | 3.0.3 | WSGI utility | Development server not production-ready |
| Jinja2 | 3.1.4 | Template engine | Current version |
| blinker | 1.9.0 | Signal support | Flask dependency |
| click | 8.1.8 | CLI framework | Flask dependency |
| itsdangerous | 2.2.0 | Signed cookies | Flask dependency (not utilized) |
| MarkupSafe | 3.0.2 | HTML escaping | Jinja2 dependency |

**Security Implications:**
- **Python 3.8.17:** End-of-life (October 2024), no longer receiving security patches
- **Debian Buster:** Base image EOL (June 2022), no security updates
- **PhantomJS:** Abandoned project (last release 2016), known security vulnerabilities including CVE-2019-17221
- **Werkzeug Development Server:** Not hardened for production (no DoS protection, limited connection handling)
- **Missing Security Libraries:** No `flask-limiter` (rate limiting), `flask-wtf` (CSRF), `bcrypt` (password hashing), `flask-talisman` (security headers)

**Dependency File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/requirements.txt`

### Monitoring & Logging

**Application Logging:**
- **Status:** ❌ NOT IMPLEMENTED
- No explicit logging statements in application code
- No configuration of Python `logging` module
- No log files or log destinations configured

**Security Event Visibility:**
- ❌ No authentication attempt logging
- ❌ No authorization failure logging
- ❌ No failed login tracking
- ❌ No JWT validation error logging
- ❌ No access logs for sensitive endpoints (`/dashboard`)

**Default Flask Logging:**
- Flask/Werkzeug logs HTTP requests to stderr by default
- Logs include: timestamp, IP address, HTTP method, path, status code
- **Security Concern:** No correlation IDs, no user context, insufficient for security monitoring

**Monitoring Tools:**
- ❌ No APM (Application Performance Monitoring) integration
- ❌ No SIEM (Security Information and Event Management) integration
- ❌ No alerting on suspicious activity
- ❌ No metrics collection (Prometheus, StatsD, etc.)

**Docker Health Check:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/docker-compose.yml`
- **Implementation:** `curl -f http://localhost:5003`
- **Limitations:** Only checks HTTP 200 response, no application-level health validation

**Audit Trail Gaps:**
- No record of who accessed what data and when
- No evidence for security incident investigation
- No compliance audit trail (GDPR, SOC 2, etc.)
- No tracking of configuration changes

---

## 7. Overall Codebase Indexing

This Flask application follows a minimal monolithic structure typical of CTF challenges and proof-of-concept demonstrations. The codebase consists of a single Python application file (`app.py` with 73 lines), one HTML template file for the login form, and standard Docker deployment configuration. The directory organization is flat with no complex module hierarchy, making security-relevant components easily discoverable but also highlighting the lack of separation between concerns.

**Directory Structure:**
```
/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/
├── app/                          # Application directory
│   ├── app.py                    # Main Flask application (73 lines, 2252 bytes)
│   ├── Dockerfile                # Container build definition (29 lines)
│   ├── requirements.txt          # Python dependencies (11 packages)
│   └── templates/                # Jinja2 templates directory
│       └── login.html            # Login form template (17 lines)
├── outputs/                      # Output directory for scan results
│   ├── scans/                    # Security scan outputs
│   └── schemas/                  # API schema storage (empty - no schemas found)
├── .env                          # Environment variables (FLAG storage)
├── docker-compose.yml            # Docker orchestration configuration
├── Makefile                      # Build automation (out-of-scope: CLI only)
└── benchmark.json                # CTF challenge metadata
```

**Code Organization Patterns:**
- **Single-File Application:** All route handlers, authentication logic, and authorization checks in one 73-line file (`app.py`)
- **No Modularization:** No separation into blueprints, modules, or packages
- **Inline Configuration:** Hardcoded user credentials and security settings within application code
- **Template Location:** Standard Flask convention with `templates/` subdirectory

**Build and Orchestration Tools:**
- **Make:** Build automation via `Makefile` with targets for build, run, clean operations (not network-accessible)
- **Docker Compose:** Service orchestration defining single web service on port 5003
- **Docker Multi-Stage Build:** Uses Debian Buster base, installs PhantomJS, copies application files, runs Flask on port 5003

**Security Component Discoverability:**
- **HIGH:** All authentication code concentrated in lines 20-35 (single `/login` route handler)
- **HIGH:** All authorization checks inline within route handlers (lines 44-49 for `/profile`, lines 61-67 for `/dashboard`)
- **HIGH:** User credentials immediately visible at lines 9-12
- **HIGH:** JWT configuration exposed at lines 14, 27
- **MEDIUM:** Session cookie configuration at line 30
- **LOW:** No middleware patterns or decorators that would require tracing across files

**Notable Conventions:**
- **Flask Patterns:** Standard `@app.route()` decorator syntax for route definitions
- **JWT Library:** PyJWT 2.10.1 used directly without wrapper or abstraction layer
- **Template Rendering:** Mix of `render_template()` (line 35 for `login.html`) and `render_template_string()` (lines 47, 49 with inline HTML strings)
- **Error Handling:** Basic try-except blocks for JWT decoding (lines 43-51, 60-68) with generic error messages

**Impact on Security Analysis:**
- **Positive:** Simple flat structure enables rapid identification of all security-critical code paths
- **Positive:** No hidden authentication mechanisms or obfuscated authorization logic
- **Negative:** Lack of modularization means no reusable security decorators or middleware
- **Negative:** No separation between configuration and code makes hardcoded secrets more likely
- **Negative:** Single-file approach prevents security-focused code review by component

**Testing Framework:**
- ❌ No test directory or test files detected
- ❌ No pytest, unittest, or other testing framework configuration
- **Impact:** No security test coverage, no regression testing for vulnerability fixes

**Documentation:**
- ❌ No README.md file
- ❌ No API documentation
- ❌ No inline code comments in `app.py`
- **Available:** `benchmark.json` contains CTF challenge metadata (name, difficulty, category)

---

## 8. Critical File Paths

### Configuration Files
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile` - Container build definition, installs PhantomJS (unused), sets FLAG environment variable
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/docker-compose.yml` - Service orchestration, port mapping 5003:5003, health check configuration
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/.env` - Environment variables containing FLAG value
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/benchmark.json` - CTF challenge metadata

### Authentication & Authorization
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 14) - JWT SECRET_KEY declaration (hardcoded, unused)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 9-12) - User credentials dictionary (plaintext passwords)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 20-35) - Login endpoint and JWT token generation
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 27) - JWT encode with algorithm='none' (CRITICAL VULNERABILITY)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 30) - Cookie configuration without security flags
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 37-52) - Profile endpoint with role-based content
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 44) - JWT decode with verify_signature=False (CRITICAL VULNERABILITY)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 54-69) - Dashboard endpoint with admin authorization
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 61) - JWT decode with verify_signature=False (CRITICAL VULNERABILITY)

### API & Routing
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 16-18) - Root endpoint redirecting to login
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 20-35) - Login form and authentication handler
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 37-52) - User profile endpoint
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 54-69) - Admin dashboard endpoint (flag retrieval)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/templates/login.html` - Login form template (no CSRF protection)

### Data Models & DB Interaction
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 9-12) - In-memory user data structure (no database)

### Dependency Manifests
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/requirements.txt` - Python package dependencies (Flask 3.0.3, PyJWT 2.10.1, cryptography 42.0.7)

### Sensitive Data & Secrets Handling
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 14) - SECRET_KEY definition (unused)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 9-12) - Hardcoded user credentials
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 64) - Flag retrieval from environment variable
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/.env` (line 1) - FLAG environment variable value

### Middleware & Input Validation
- ❌ No middleware files detected
- ❌ No input validation modules detected
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (lines 23-26) - Basic form input handling (no validation)

### Logging & Monitoring
- ❌ No logging configuration files detected
- ❌ No monitoring configuration detected

### Infrastructure & Deployment
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile` - Container build instructions (Debian Buster base, PhantomJS installation)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/docker-compose.yml` - Service definition and health check
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/Makefile` - Build automation (out-of-scope: local CLI only)

### CTF Flag Storage
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/.env` (line 1) - FLAG environment variable
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile` (lines 21-22) - FLAG passed as build ARG and set as ENV
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 64) - Flag retrieval: `os.getenv('FLAG', 'No flag found')`
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` (line 65) - Flag returned to authorized users

---

## 9. XSS Sinks and Render Contexts

### Network Surface Focus
This analysis covers only network-accessible endpoints (4 HTTP routes). Out-of-scope CLI tools, build scripts, and local utilities have been excluded.

### Summary
**NO EXPLOITABLE XSS SINKS FOUND** - While the application uses `render_template_string()` (a known dangerous function), the current implementation uses only hardcoded template strings with no user input interpolation.

### Template Rendering Analysis

**Potential Sink: render_template_string() Usage**

**Location 1 - Admin Profile Template:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Line:** 47
- **Endpoint:** `GET /profile`
- **Render Context:** Jinja2 Server-Side Template
- **Code:**
```python
return render_template_string('<h1>ADMIN</h1><a style="display:none" href="/dashboard">Dashboard</a>')
```
- **User Input Flow:** None - template string is a hardcoded literal
- **XSS Risk:** ✅ **NOT VULNERABLE** (no user input in template)
- **SSTI Risk:** ✅ **NOT VULNERABLE** (no user input in template definition)

**Location 2 - User Profile Template:**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py`
- **Line:** 49
- **Endpoint:** `GET /profile`
- **Render Context:** Jinja2 Server-Side Template
- **Code:**
```python
return render_template_string('<h1>USER</h1>')
```
- **User Input Flow:** None - template string is a hardcoded literal
- **XSS Risk:** ✅ **NOT VULNERABLE** (no user input in template)
- **SSTI Risk:** ✅ **NOT VULNERABLE** (no user input in template definition)

**Analysis:**
Although `render_template_string()` is a dangerous function commonly associated with Server-Side Template Injection (SSTI) vulnerabilities, the current implementation is safe because:
1. Template strings are hardcoded literals with no variable interpolation
2. JWT payload's `role` field only controls conditional logic (which template to use), not template content
3. No user-controlled data flows into the template string parameter

**Security Note:** This is still a **risky coding pattern** that should be refactored to use `render_template()` with separate template files.

### Login Form Template Analysis

**File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/templates/login.html`

**Findings:**
- ✅ Static HTML form with no JavaScript
- ✅ No dynamic content rendering
- ✅ No Jinja2 template variables (`{{ }}` or `{% %}`)
- ✅ No user input displayed in HTML
- ✅ No XSS sinks detected

### Comprehensive XSS Sink Search Results

**HTML Body Context Sinks:** ❌ None found
- `innerHTML`, `outerHTML`, `document.write()`, `insertAdjacentHTML()` not present
- jQuery HTML manipulation methods (`.html()`, `.append()`, etc.) not present

**HTML Attribute Context Sinks:** ❌ None found
- Event handlers (`onclick`, `onerror`, `onload`, etc.) only in static HTML
- URL-based attributes (`href`, `src`) only hardcoded (e.g., `/dashboard` link)

**JavaScript Context Sinks:** ❌ None found
- `eval()`, `Function()`, `setTimeout/setInterval` with strings not present
- No JavaScript files in application

**CSS Context Sinks:** ❌ None found
- `element.style` properties not used
- Only static inline `style="display:none"` attribute at line 47

**URL Context Sinks:** ❌ None found
- `location.href`, `window.open()`, `history.pushState()` not present
- All redirects use server-side `redirect(url_for(...))` (safe)

### Other Template Files
**Files Searched:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/templates/`
**Result:** Only `login.html` exists - no other template files found

### Conclusion
This application has **NO exploitable XSS sinks** in network-accessible code paths. The use of `render_template_string()` represents a dangerous coding pattern but is currently implemented safely. However, the application lacks Content Security Policy (CSP) headers which would provide defense-in-depth against potential future XSS vulnerabilities.

---

## 10. SSRF Sinks

### Network Surface Focus
This analysis covers only network-accessible code paths. Out-of-scope local-only utilities and build scripts have been excluded.

### Summary
**NO SSRF SINKS FOUND** - This application performs zero outbound HTTP requests and has no mechanisms for user input to influence server-side network operations.

### Comprehensive SSRF Analysis

**HTTP Client Libraries:** ❌ None imported or used
- `requests`, `urllib`, `urllib2`, `urllib3`, `httplib`, `http.client` not present
- `aiohttp`, `httpx`, `pycurl` not present

**URL Operations:** ❌ None found
- `urlopen()`, `file_get_contents()`, `fopen()` with URLs not present
- No file inclusion mechanisms that accept URLs

**Subprocess/Command Execution:** ❌ None found
- `subprocess.call/run/Popen`, `os.popen()`, `os.system()` not present
- No `curl`, `wget`, or shell command execution
- **Only `os` module usage:** Line 64 - `os.getenv('FLAG', 'No flag found')` (safe environment variable read)

**PhantomJS Analysis - INSTALLED BUT COMPLETELY UNUSED:**
- **Installation Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile` line 12
- **Dockerfile Command:** `RUN apt-get update && apt-get install -y --no-install-recommends phantomjs`
- **Application Usage:** ❌ **ZERO** - No subprocess calls, no rendering scripts, no PhantomJS invocation anywhere in `app.py`
- **Security Assessment:** Unused dependency creating unnecessary attack surface
- **Recommendation:** Remove from Dockerfile to reduce container image vulnerabilities

**Redirect Handlers - SAFE (Internal Only):**
All redirect operations use Flask's `url_for()` for internal routing with no user-controlled URLs:

| File Location | Line | Code | User Control |
|--------------|------|------|--------------|
| `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` | 18 | `redirect(url_for('login'))` | ❌ None |
| `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` | 29 | `redirect(url_for('profile'))` | ❌ None |
| `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` | 41 | `redirect(url_for('login'))` | ❌ None |
| `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/app.py` | 58 | `redirect(url_for('login'))` | ❌ None |

**Finding:** All redirects target hardcoded internal Flask routes with no user input in redirect destinations.

### SSRF Sink Categories - All Negative

**Headless Browsers & Render Engines:** ❌ None
- Puppeteer, Playwright, Selenium not present
- PhantomJS installed but never invoked

**Media Processors:** ❌ None
- ImageMagick, GraphicsMagick, FFmpeg not present
- No image processing or media manipulation

**Link Preview & Unfurlers:** ❌ None
- No URL metadata extraction
- No oEmbed endpoint fetching

**SSO/OIDC Discovery & JWKS Fetchers:** ❌ None
- No OpenID Connect discovery
- No JWKS (JSON Web Key Set) fetching
- JWT validation uses local hardcoded logic only

**Webhook Handlers:** ❌ None
- No webhook receivers
- No callback endpoints
- No external notification handlers

**External API Integrations:** ❌ None
- No third-party API calls
- Fully self-contained application

**Package/Plugin Installers:** ❌ None
- No "install from URL" functionality
- No dynamic plugin loading

**Monitoring & Health Checks:** ⚠️ Docker health check only (not user-controllable)
- Docker Compose health check: `curl -f http://localhost:5003`
- **Not an SSRF vector:** Runs in container context, not triggered by user input

### Network Traffic Analysis

**Inbound Traffic:**
- HTTP server listening on `0.0.0.0:5003`
- 4 endpoints: `/`, `/login`, `/profile`, `/dashboard`

**Outbound Traffic:**
- **ZERO outbound HTTP/HTTPS requests detected**
- No DNS lookups from user input
- No external service dependencies
- No file fetching from remote URLs

### Endpoint-by-Endpoint SSRF Assessment

| Endpoint | User Input | Network Operations | SSRF Risk |
|----------|-----------|-------------------|-----------|
| `GET /` | None | Internal redirect only | ❌ None |
| `GET/POST /login` | `username`, `password` | Local authentication check | ❌ None |
| `GET /profile` | JWT token | Token decode, template render | ❌ None |
| `GET /dashboard` | JWT token | Environment variable read | ❌ None |

### Conclusion
This application has **ZERO SSRF attack surface**. It performs no outbound network requests, has no HTTP client libraries, and provides no mechanisms for user input to influence server-side URL fetching or external connections. The installed PhantomJS package is completely unused and should be removed to reduce container image size and eliminate unnecessary attack surface.

**RECOMMENDATION:** Remove PhantomJS from `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-091-24/app/Dockerfile` line 12 as it creates unnecessary CVE exposure without providing any functionality.