IIS (Microsoft Web Server)

Cross-platform resources for IIS (Microsoft Web Server): curated HTB machines, PortSwigger labs and TryHackMe rooms with validated writeups and related skills.

This page aggregates cross-platform resources to practice IIS (Microsoft Web Server): retired Hack The Box machines, PortSwigger Web Security Academy labs and TryHackMe rooms, plus curated resources (HackTricks, PortSwigger, etc.) and related skills.

Coverage: 11 challenges across 2 platforms — 8 HackTheBox · 3 TryHackMe. 8 with a Spanish writeup, 8 with a video writeup.

Where to start

Ordered by actual difficulty. At the same level: isolated lab first, then the guided room, and the full machine last.

1. HackTheBox — Bounty (Fácil) · 🇪🇸 🇬🇧 📹
2. HackTheBox — Devel (Fácil) · 🇪🇸 🇬🇧 📹
3. HackTheBox — Grandpa (Fácil) · 🇪🇸 🇬🇧 📹
4. HackTheBox — Granny (Fácil) · 🇪🇸 🇬🇧 📹
5. TryHackMe — Conti (Medium · ~45 min) · 🇬🇧
6. TryHackMe — Detecting AD Initial Access (Medium · ~60 min) · 🇬🇧

Curated resources

Source	Link
HackTricks	https://book.hacktricks.wiki/en/network-services-pentesting/pentesting-web/iis-internet-information-services.html

HTB machines practicing IIS (Microsoft Web Server) (8)

Machine	OS	Difficulty	Writeup
Bounty	Windows	EASY	🇪🇸 🇬🇧 📹
Conceal	Windows	HARD	🇪🇸 🇬🇧 📹
Devel	Windows	EASY	🇪🇸 🇬🇧 📹
Grandpa	Windows	EASY	🇪🇸 🇬🇧 📹
Granny	Windows	EASY	🇪🇸 🇬🇧 📹
RE	Windows	HARD	🇪🇸 🇬🇧 📹
SecNotes	Windows	MEDIUM	🇪🇸 🇬🇧 📹
Worker	Windows	MEDIUM	🇪🇸 🇬🇧 📹

TryHackMe rooms practicing IIS (Microsoft Web Server) (3)

Room	Difficulty	Type	Access	Official
Conti	MEDIUM	Challenge	🟢 Free	Open
Detecting AD Initial Access	MEDIUM	Walkthrough	🔵 VIP	Open
Legal Considerations in DFIR	MEDIUM	Walkthrough	🟢 Free	Open

Related skills

• /en/skills/webdav

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Last updated: 2026-08-13