Overview

The machine starts with provided credentials that grant SMB and RDP access, enumeration of the Management folder reveals an IT changelog mentioning a database, and PowerShell history leaks the administrator password, which when used with runas yields a privileged shell to read the root flag.

Enumeration

Start with nmap scan

This is assumed breach box and we're given the credentials tyler.ramsey:P@ssw0rd!

So let's see what we can do with those creds against the 3 open ports

SMB

There isn't kerberos port or HTTP port that might need any vhosting stuff so there is no need to add any entries in the hosts file Testing the creds, it has access over the SMB and RDP so let's start with the easy ones

bash
┌─[vpn.coursestack.com 10.200.80.22]─[jimmex@attacker]─[~/hacksmarter/slayer]
└──╼ [★]$ nxc smb 10.1.124.85 -u tyler.ramsey -p P@ssw0rd!
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO [*] Windows 11 / Server 2025 Build 26100 x64 (name:EC2AMAZ-M1LFCNO) (domain:EC2AMAZ-M1LFCNO) (signing:False) (SMBv1:None)
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO [+] EC2AMAZ-M1LFCNO\tyler.ramsey:P@ssw0rd!
┌─[vpn.coursestack.com 10.200.80.22]─[jimmex@attacker]─[~/hacksmarter/slayer]
└──╼ [★]$ nxc rdp 10.1.124.85 -u tyler.ramsey -p P@ssw0rd!
RDP 10.1.124.85 3389 EC2AMAZ-M1LFCNO [*] Windows 10 or Windows Server 2016 Build 26100 (name:EC2AMAZ-M1LFCNO) (domain:EC2AMAZ-M1LFCNO) (nla:True)
RDP 10.1.124.85 3389 EC2AMAZ-M1LFCNO [+] EC2AMAZ-M1LFCNO\tyler.ramsey:P@ssw0rd! (Pwn3d!)

Not much we can do about SMB though so let's get on that RDP

bash
┌─[vpn.coursestack.com 10.200.80.22]─[jimmex@attacker]─[~/hacksmarter/slayer]
└──╼ [★]$ nxc smb 10.1.124.85 -u tyler.ramsey -p P@ssw0rd! --shares
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO [*] Windows 11 / Server 2025 Build 26100 x64 (name:EC2AMAZ-M1LFCNO) (domain:EC2AMAZ-M1LFCNO) (signing:False) (SMBv1:None
)
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO [+] EC2AMAZ-M1LFCNO\tyler.ramsey:P@ssw0rd!
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO [*] Enumerated shares
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO Share Permissions Remark
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO ----- ----------- ------
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO ADMIN$ Remote Admin
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO C$ Default share
SMB 10.1.124.85 445 EC2AMAZ-M1LFCNO IPC$ READ Remote IPC

RDP

So let's start an RDP session

bash
xfreerdp3 /v:10.1.124.85 /u:tyler.ramsey /p:P@ssw0rd!

Nothing on Tyler's Desktop, we need to dig a little deeper ss_20260809_190428.png

There isn't much given to us by this user so let's look around ss_20260809_190610.png

There is only one more user on this box other than the administrator and Tyler

bash
PS C:\Users> ls

    Directory: C:\Users


Mode LastWriteTime Length Name
---- ------------- ------ ----
d----- 10/14/2025 10:57 PM Administrator
d----- 9/30/2025 6:38 PM alice.wonderland
d-r--- 11/20/2024 11:32 PM Public
d----- 8/10/2026 2:01 AM tyler.ramsey

Looking around for files we find this folder, so let's see what we can find starting by the most interesting ones

bash
PS C:\Management> ls


    Directory: C:\Management


Mode LastWriteTime Length Name
---- ------------- ------ ----
-a---- 9/30/2025 6:18 PM 2030 Board Meeting Minutes - 2025-09-10.pdf
-a---- 9/30/2025 6:18 PM 1940 Customer Feedback Summary - 2025 Q3.pdf
-a---- 9/30/2025 6:18 PM 2044 Executive Summary - Q3 2025.pdf
-a---- 9/30/2025 6:18 PM 1966 Financial Overview - FY2025 Q3.pdf
-a---- 9/30/2025 6:18 PM 1916 HR Headcount & Org Chart - 2025-09.pdf
-a---- 9/30/2025 6:18 PM 1962 IT Change Log - Sep 2025.pdf
-a---- 9/30/2025 6:18 PM

Looked into each file and nothing was useful.

Checking the PowerShell history, we see that Tyle changed the administrator password using Command Prompt image

This means we can use this password with the runas to spawn a shell act as administrator And as you can see we got the root flag image

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