Enteprise is a room on tryhackme that is a CTF challenge.

Difficulty: 👺Hard

You just landed in an internal network. You scan the network and there's only the Domain Controller...

First enumeration

I’ll start with a nmap scan to identify what services the target is running.

sudo nmap -sV -T4 $IP
#RESULTS#
Starting Nmap 7.93 ( <https://nmap.org> ) at 2025-05-15 15:06 UTC
Nmap scan report for ip-10-10-140-26.eu-west-1.compute.internal (10.10.140.26)
Host is up (0.00053s latency).
Not shown: 65505 closed tcp ports (reset)
PORT      STATE SERVICE       VERSION
53/tcp    open  domain        Simple DNS Plus
80/tcp    open  http          Microsoft IIS httpd 10.0
88/tcp    open  kerberos-sec  Microsoft Windows Kerberos (server time: 2025-05-15 15:07:00Z)
135/tcp   open  msrpc         Microsoft Windows RPC
139/tcp   open  netbios-ssn   Microsoft Windows netbios-ssn
389/tcp   open  ldap          Microsoft Windows Active Directory LDAP (Domain: ENTERPRISE.THM0., Site: Default-First-Site-Name)
445/tcp   open  microsoft-ds?
464/tcp   open  kpasswd5?
593/tcp   open  ncacn_http    Microsoft Windows RPC over HTTP 1.0
636/tcp   open  tcpwrapped
3268/tcp  open  ldap          Microsoft Windows Active Directory LDAP (Domain: ENTERPRISE.THM0., Site: Default-First-Site-Name)
3269/tcp  open  tcpwrapped
3389/tcp  open  ms-wbt-server Microsoft Terminal Services
5357/tcp  open  http          Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
5985/tcp  open  http          Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
7990/tcp  open  http          Microsoft IIS httpd 10.0
9389/tcp  open  mc-nmf        .NET Message Framing
47001/tcp open  http          Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
49664/tcp open  msrpc         Microsoft Windows RPC
49665/tcp open  msrpc         Microsoft Windows RPC
49666/tcp open  msrpc         Microsoft Windows RPC
49668/tcp open  ncacn_http    Microsoft Windows RPC over HTTP 1.0
49669/tcp open  msrpc         Microsoft Windows RPC
49670/tcp open  msrpc         Microsoft Windows RPC
49671/tcp open  msrpc         Microsoft Windows RPC
49673/tcp open  msrpc         Microsoft Windows RPC
49675/tcp open  msrpc         Microsoft Windows RPC
49704/tcp open  msrpc         Microsoft Windows RPC
49708/tcp open  msrpc         Microsoft Windows RPC
49847/tcp open  msrpc         Microsoft Windows RPC
MAC Address: 02:F1:78:CC:0B:A7 (Unknown)
Service Info: Host: LAB-DC; OS: Windows; CPE: cpe:/o:microsoft:windows

Service detection performed. Please report any incorrect results at <https://nmap.org/submit/> .
Nmap done: 1 IP address (1 host up) scanned in 80.80 seconds

and this nmap:

sudo nmap -sC -T4 -p- 10.10.140.26
#RESULTS#
Starting Nmap 7.93 ( <https://nmap.org> ) at 2025-05-15 18:54 UTC
Nmap scan report for ip-10-10-140-26.eu-west-1.compute.internal (10.10.140.26)
Host is up (0.00080s latency).
Not shown: 65505 closed tcp ports (reset)
PORT      STATE SERVICE
53/tcp    open  domain
80/tcp    open  http
| http-methods: 
|_  Potentially risky methods: TRACE
|_http-title: Site doesn't have a title (text/html).
88/tcp    open  kerberos-sec
135/tcp   open  msrpc
139/tcp   open  netbios-ssn
389/tcp   open  ldap
445/tcp   open  microsoft-ds
464/tcp   open  kpasswd5
593/tcp   open  http-rpc-epmap
636/tcp   open  ldapssl
3268/tcp  open  globalcatLDAP
3269/tcp  open  globalcatLDAPssl
3389/tcp  open  ms-wbt-server
| ssl-cert: Subject: commonName=LAB-DC.LAB.ENTERPRISE.THM
| Not valid before: 2025-05-14T15:00:05
|_Not valid after:  2025-11-13T15:00:05
| rdp-ntlm-info: 
|   Target_Name: LAB-ENTERPRISE
|   NetBIOS_Domain_Name: LAB-ENTERPRISE
|   NetBIOS_Computer_Name: LAB-DC
|   DNS_Domain_Name: LAB.ENTERPRISE.THM
|   DNS_Computer_Name: LAB-DC.LAB.ENTERPRISE.THM
|   DNS_Tree_Name: ENTERPRISE.THM
|   Product_Version: 10.0.17763
|_  System_Time: 2025-05-15T18:54:39+00:00
|_ssl-date: 2025-05-15T18:54:39+00:00; +1s from scanner time.
5357/tcp  open  wsdapi
5985/tcp  open  wsman
7990/tcp  open  unknown
9389/tcp  open  adws
47001/tcp open  winrm
49664/tcp open  unknown
49665/tcp open  unknown
49666/tcp open  unknown
49668/tcp open  unknown
49669/tcp open  unknown
49670/tcp open  unknown
49671/tcp open  unknown
49673/tcp open  unknown
49675/tcp open  unknown
49704/tcp open  unknown
49708/tcp open  unknown
49847/tcp open  unknown
MAC Address: 02:F1:78:CC:0B:A7 (Unknown)

Host script results:
| smb2-security-mode: 
|   311: 
|_    Message signing enabled and required
|_nbstat: NetBIOS name: LAB-DC, NetBIOS user: <unknown>, NetBIOS MAC: 02f178cc0ba7 (unknown)
| smb2-time: 
|   date: 2025-05-15T18:54:39
|_  start_date: N/A

Nmap done: 1 IP address (1 host up) scanned in 214.65 seconds

The first thing we can assume, is that we are dealing with a Domain Controller because this machine is running a DNS server on port 53, Kerberos in port 88, and ADWS on port 9389.

Found these dns names, so lets put them into my known hosts:

nano /etc/hosts

image.png

I can see that the server is running a IIS on ports 80 and 7990, so lets check it:

IIS on port 80:

on the source code it has nothing usefull…

on the source code it has nothing usefull…

lets try to enumerate the directories!

ffuf -u <http://10.10.140.26/FUZZ> -w /usr/share/wordlists/seclists/Discovery/Web-Content/directory-list-lowercase-2.3-big.txt -t 100 -c -v -recursion -e .php,.html,.txt

we can see that the that the robots.txt is avaiable!

image.png

nothing useful.