Individual skill
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.
internal/tools/skills/data/web-application-security/exploiting-http-request-smuggling/SKILL.md
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- Last checked
- Nov 9, 2026
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- Repository last updated
- Nov 9, 2026
- License
- Apache-2.0
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- cybersecurity Repository topic
- security Repository topic
- bug-bounty Repository topic
- automation Repository topic
- autonomous-pentesting Repository topic
- ai-agent Repository topic
- ai-security Repository topic
- ethical-hacking Repository topic
- golang Repository topic
- penetration-testing Repository topic
- penetration-testing Declared skill tag
- request-smuggling Declared skill tag
- http-desync Declared skill tag
- web-security Declared skill tag
- burpsuite Declared skill tag
- owasp Declared skill tag
- writing Derived category
- security Derived category
- testing Derived category
- security-application Derived category
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# Exploiting HTTP Request Smuggling
## 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
### How to CONFIRM a Hit (avoid false negatives)
- The positive signal is a **desync**, not a single clean response. Prove it one of two ways: (a) a time-delay probe (incomplete chunk / mismatched length) that hangs ~5-10s versus an instant baseline, or (b) a smuggled prefix that poisons the *next* request on the same connection — you (or a victim socket) receive a response for an endpoint you did not request, a 400/405 on a normal follow-up request, or your prefix reflected back.
- Always send the paired follow-up request. One smuggling request returning 200 proves nothing; the proof is the second request being corrupted, redirected, or delayed.
- Confirm with a socket-reuse test: fire the attack request, then immediately a normal request on the SAME connection and diff it against the same request on a fresh connection.