HTB Checkpoint Writeup

Checkpoint is a medium difficulty Windows box on HackTheBox. It’s an Active Directory environment and you’re handed initial credentials to start.

alex.turner : Checkpoint2024!

Reconnaissance#

Port Scan#

Fast TCP sweep first.

┌──(kali㉿kali)-[~/htb/checkpoint]
└─$ sudo nmap 10.129.171.231 -p- --min-rate 5000
Not shown: 65514 filtered tcp ports (no-response)
PORT      STATE SERVICE
53/tcp    open  domain
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
5985/tcp  open  wsman
9389/tcp  open  adws

Standard DC port profile. Service scan against the interesting ones:

┌──(kali㉿kali)-[~/htb/checkpoint]
└─$ sudo nmap 10.129.171.231 -p 389,636,445,88,135,139,5985 -sC -sV
PORT     STATE SERVICE       VERSION
88/tcp   open  kerberos-sec  Microsoft Windows Kerberos
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: checkpoint.htb, Site: Default-First-Site-Name)
445/tcp  open  microsoft-ds?
636/tcp  open  tcpwrapped
5985/tcp open  http          Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)

Service Info: Host: DC01; OS: Windows; CPE: cpe:/o:microsoft:windows

Domain is checkpoint.htb, host is DC01. LDAP signing enforced, SMB signing required, Server 2025 Build 26100. Clock skew of ~7 hours - fix that immediately:

sudo sh -c 'echo "10.129.171.231 dc01.checkpoint.htb checkpoint.htb" >> /etc/hosts'
sudo ntpdate -u 10.129.171.231