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.

IIS (Microsoft Web Server)

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.

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
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: 2026-05-09