> ## Documentation Index
> Fetch the complete documentation index at: https://rootea.es/llms.txt
> Use this file to discover all available pages before exploring further.

# 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](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](/en/htb/machines/windows/facil/bounty)     | Windows | <span className="dbadge dbadge-easy">EASY</span>     |
| [Conceal](/en/htb/machines/windows/dificil/conceal) | Windows | <span className="dbadge dbadge-hard">HARD</span>     |
| [Devel](/en/htb/machines/windows/facil/devel)       | Windows | <span className="dbadge dbadge-easy">EASY</span>     |
| [Grandpa](/en/htb/machines/windows/facil/grandpa)   | Windows | <span className="dbadge dbadge-easy">EASY</span>     |
| [Granny](/en/htb/machines/windows/facil/granny)     | Windows | <span className="dbadge dbadge-easy">EASY</span>     |
| [RE](/en/htb/machines/windows/dificil/re)           | Windows | <span className="dbadge dbadge-hard">HARD</span>     |
| [SecNotes](/en/htb/machines/windows/medio/secnotes) | Windows | <span className="dbadge dbadge-medium">MEDIUM</span> |
| [Worker](/en/htb/machines/windows/medio/worker)     | Windows | <span className="dbadge dbadge-medium">MEDIUM</span> |

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

| Room                                                                               | Difficulty                                         | Type        | Access  | Official                                                          |
| ---------------------------------------------------------------------------------- | -------------------------------------------------- | ----------- | ------- | ----------------------------------------------------------------- |
| [Conti](/en/tryhackme/rooms/contiransomwarehgh)                                    | <span className="dbadge dbadge-easy">MEDIUM</span> | Challenge   | 🟢 Free | [Open](https://tryhackme.com/room/contiransomwarehgh)             |
| [Detecting AD Initial Access](/en/tryhackme/rooms/detectingadinitialaccess)        | <span className="dbadge dbadge-easy">MEDIUM</span> | Walkthrough | 🔵 VIP  | [Open](https://tryhackme.com/room/detectingadinitialaccess)       |
| [Legal Considerations in DFIR](/en/tryhackme/rooms/dfirprocesslegalconsiderations) | <span className="dbadge dbadge-easy">MEDIUM</span> | Walkthrough | 🟢 Free | [Open](https://tryhackme.com/room/dfirprocesslegalconsiderations) |

## Related skills

* [/en/skills/webdav](/en/skills/webdav)

***

← [Back to the full glossary](/en/glossary)

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*Last updated: 2026-05-09*