tl;dr: Misconfigured IIS servers remain a goldmine for bug bounty hunters, with attack vectors including internal IP disclosure via HTTP/1.0 requests, virtual host brute-forcing past HTTPAPI 2.0 404s, and IIS tilde (8.3 shortname) enumeration that can be resolved using LLMs, GitHub dorks, or BigQuery's public GitHub dataset. High-value targets include web.config (containing machine keys for ViewState deserialization RCE), bin directory DLLs accessible via cookieless session path tricks like `/(S(X))/b/(S(X))in/`, and trace.axd/elmah.axd debug endpoints. Other techniques cover reverse proxy path confusion, NTFS alternate data stream auth bypasses, file upload extensions that render as HTML, and HPP for WAF evasion.