TryHackMe > Windows Machines

Retro

New high score!

windows wordpress web-shell rce php sweet-potato rdp recycle-bin browsing-history cve-2019-1388

November 4, 2025 • September 6, 2025 • Hard

AllSignsPoint2Pwnage

A room that contains a rushed Windows based Digital Sign system. Can you breach it?

windows ftp xampp php smb reverse-shell metasploit autologon av-evasion vnc rce

November 4, 2025 • September 4, 2025 • Medium

TryHackMe > Windows Machines

Hack Smarter Security

Can you hack the hackers?

windows ftp omsa cve-2020-5377 cve-2021-21514 file-read iis service-exploit binary-hijacking av-evasion reverse-shell hacksmarter

November 4, 2025 • September 1, 2025 • Medium

TryHackMe > Windows Machines

Weasel

I think the data science team has been a bit fast and loose with their project resources.

windows jupyter web-shell reverse-shell metasploit autologon rdp alwaysinstallelevated wsl smb python private-key-discovery

November 4, 2025 • September 1, 2025 • Medium

TryHackMe > Windows Machines

CyberLens

Can you exploit the CyberLens web server and discover the hidden flags?

windows apache-tika command-injection reverse-shell metasploit alwaysinstallelevated cve-2018-1335 hacksmarter rce

November 4, 2025 • August 30, 2025 • Easy

TryHackMe > Windows Machines

Anthem

Exploit a Windows machine in this beginner level challenge.

windows umbraco rce rdp

November 4, 2025 • August 30, 2025 • Easy

TryHackMe > Windows Machines

Blueprint

Hack into this Windows machine and escalate your privileges to Administrator.

windows smb oscommerce reverse-shell php mimikatz metasploit rce ntlm

November 4, 2025 • August 30, 2025 • Easy

TryHackMe > Windows Machines

Year of the Owl

The foolish owl sits on his throne...

windows year-of-the snmp dictionary-attack smb pass-the-hash sam ntlm recycle-bin winrm

November 4, 2025 • August 29, 2025 • Hard

TryHackMe > Windows Machines

Relevant

Penetration Testing Challenge.

windows iis smb rdp reverse-shell aspx token-impersonation sweet-potato rce

November 4, 2025 • August 6, 2025 • Medium

TryHackMe > Windows Machines

HackPark

Bruteforce a websites login with Hydra, identify and use a public exploit then escalate your privileges on this Windows machine!

windows blogenginenet dictionary-attack rce cve-2019-6714 reverse-shell ascx autologon rdp service-exploit unquoted-service-path

November 4, 2025 • July 25, 2025 • Medium

TryHackMe > Windows Machines

Alfred

Exploit Jenkins to gain an initial shell, then escalate your privileges by exploiting Windows authentication tokens.

windows jenkins rce reverse-shell token-impersonation process-migration metasploit

November 4, 2025 • July 25, 2025 • Easy

TryHackMe > Windows Machines

Steel Mountain

Hack into a Mr. Robot themed Windows machine. Use metasploit for initial access, utilise powershell for Windows privilege escalation enumeration...

windows rejetto-hfs cve-2014-6287 rce reverse-shell service-exploit unquoted-service-path metasploit

November 4, 2025 • July 25, 2025 • Easy

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