Tryhackme Pentest+ Path 2026 | Windows Privilege Escalation (Attacks and Exploits)

I'm working through the Tryhackme Pentest+ path as I study for the CompTIA Pentest+ [PK0-003] certification exam in 2026. I'm going through these labs and building on my Parrot OS capabilities, so I used FreeRDP + OpenVPN to connect into the Tryhackme lab. Tryhackme Room: https://tryhackme.com/room/windowsprivesc20 Previous Room: https://www.youtube.com/watch?v=3whiAS5pHH8 Learn about Impacket: https://github.com/fortra/impacket ================ Past Helpful Videos ================ Setup FreeRDP: https://www.youtube.com/watch?v=BN9WIPbMEJM Connecting to Tryhackme VPN: https://www.youtube.com/watch?v=dlzhhEzUcWs Install ParrotOS: https://www.youtube.com/watch?v=VaW3f3oeURU =========== Timestamps =========== 01:09 | Start Task 1 - Introduction 01:49 | Answer Task 1 Question 02:00 | Start Task 2 - Windows Privilege Escalation 04:33 | Answer Task 2 Question 1 04:55 | Answer Task 2 Question 2 05:17 | Start Task 3 - Harvesting Passwords from Usual Spots 19:14 | Answer Task 3 Question 1 19:45 | Answer Task 3 Question 2 21:17 | Answer Task 3 Question 3 22:39 | Answer Task 3 Question 4 23:12 | Start Task 4 - Other Quick Wins 33:09 | Answer Task 4 Question 33:26 | Start Task 5 - Abusing Service Misconfigurations 01:22:04 | Answer Task 5 Question 1 01:22:25 | Answer Task 5 Question 2 01:22:40 | Answer Task 5 Question 3 01:24:12 | Start Task 6 - Abusing dangerous privileges 01:54:48 | Answer Task 6 Question 02:14:57 | Start Task 7 - Abusing vulnerable software 02:26:16 | Answer Task 7 Question 02:26:31 | Start Task 8 - Tools of the Trade 02:29:35 | Answer Task 8 Question 02:29:43 | Start Task 9 - Conclusion 02:30:08 | Answer Task 9 Question #thm #tryhackme #pentestplus #winprivesc #winrm #impacket