March 18, 2026 · 13 minutes read

A friend of mine once told me:

If you ever spot an IIS blue screen, don’t stop there; there must be something.

Yep, he was right. That IIS splash page is not a dead end. Behind that blue window sits one of the most consistently misconfigured web servers on the www, and it’s begging you to look deeper.

So let me walk you through how I approach IIS targets during bug bounty:

table of contents

psst, psst, IIS servers, where are you? shodan

google dorking

active tech fingerprinting

ok, I found an IIS server. now what? internal IP disclosure

pwn time nuclei templates: automate the boring stuff

the HTTPAPI 2.0 dead end that isn’t

IIS tilde enumeration: the gift that keeps giving using LLMs

github dorks to resolve shortnames

using BigQuery to resolve shortnames

bruteforcing the rest with crunch

fuzzing: the IIS-specific wordlist matters

web.config: the keys to the kingdom path traversal to web.config

bin directory DLL exposure via cookieless sessions

reverse proxy…