Evasive File Smuggling with Skyhook 

The report presents Skyhook, a red-team file transfer tool that automates on-the-fly obfuscation of HTTP(S) transactions to bypass network-based controls (e.g., TLS-intercepting IDPS) and facilitate chunked uploads/downloads. It explains the dual-service architecture (Admin for configuration and Transfer for operations), the obfuscation pipeline (Base64 by default with optional AES/XOR/Blowfish/Twofish via WebAssembly), and demonstrates how directory listings, file names, and content are transformed in transit. While useful for operator efficiency and exfiltration workflows, the author emphasizes it is not a privacy/E2EE tool and acknowledges operational limitations and potential detectability as usage grows.