Attacking Active Directory as a Red Teamer or as an Attacker

Blog From Microsoft

Hi, my name is Raymond
, and I am a Microsoft Security enthusiast with over fifteen years
of experience within the Microsoft landscape. My focus has been Microsoft
Security, and specifically with the last three years out of six as a Red
Teamer. In this blog post, I will go through an attacker or Red Teamer’s
challenges when Microsoft Defender for Identity is in place

Many organizations go through a digital transformation by the increasing use
of cloud services. Understanding the current state of the cloud service is
essential as maintaining the state is a shared responsibility between the
company and its cloud provider.

Many Red Teamers and attackers use the on-premises environment as a stepping
stone to the cloud. So, a company must understand the comprehensive set of
security controls and capabilities available in Microsoft Azure, Microsoft 365,
and on-premises. Active Directory can be a source for lateral movement and an
excellent initial attack vector due to the high-value information it holds.

Microsoft Defender for Identity is a cloud-based security
solution that leverages your on-premises Active Directory signals to identify,
detect, and investigate advanced threats, compromised identities, and malicious
insider actions directed at your organization. Defender for Identity
also protects Active Directory Federation Services (AD FS) in your
environment by detecting advanced threats and providing visibility into
authentication events generated by AD FS.

The default Active Directory authentication protocol is Kerberos, an
authentication protocol based on tickets, and is known for being the target
method of many attacks. Kerberos is an authentication protocol developed by MIT
and adopted by Microsoft since Windows 2000. Kerberos can also be complicated
and as a result, hard to secure.

This blog post will go through attacking Active Directory
as a Red Teamer and having Defender for Identity in place to protect this
high-value information. What do I have to consider before I make my next move?
Let’s find out how Defender for Identity makes my job so difficult.

Attack Kill Chain

As a Red Teamer or an attacker, you want to reach your goal as quickly as
possible, preferably without noticing. The purpose and time it takes to perform
the attack differs in every scenario. Attackers are mainly financially driven
as Red Teamers have a specific pre-defined objective to reach.

Most of the attacks require multiple steps to reach their goal. Red Teamers
or attackers use some form of an attack kill chain as a process.


(Figure 1 – an
example of an attack kill chain process)


Note: With the digital transformation to the cloud
and the complexity of most attacks, a one-size-fits-all kill chain is not
feasible anymore, but the Cyber Attack Kill Chain is a good indication of how a Red
Teamer or attacker performs an attack. The graphic shown above is more focused
on compromising an endpoint, for example. 

of Active Directory

 Reconnaissance is a critical and consistent step in any kill chain. Most
information found is likely used during an attack at a later stage. Information
like server names, IP addresses, operating systems, forest architecture,
trusts, service principal names (SPNs), groups and memberships, access control
lists, and well-known security misconfigurations is probably part of every
reconnaissance phase within Active Directory.

 The challenge as a Red Teamer (or an attacker – assume I’m
referring to both throughout this blog) starts with Defender for
Identity being enabled at the reconnaissance phase.

 A Red Teamer needs to have a valid set of credentials, a
hash, or any form of authentication to communicate with Active Directory.
Attacks like phishing e-mails can contain a malicious payload that runs under
the user context. This way, a Red Teamer or attacker can perform an attack as
an authenticated user. Without any authentication, a Red Teamer uses an attack
like AS-Rep roasting and password sprays. If you are a Red
Teamer or an attacker, Defender for Identity detects this kind of attack
and alerts in almost real time.

 Lateral Movement
Active Directory

 The ultimate objective for a Red Teamer is data. For most organizations,
data is one of the most valuable assets. Getting access to all data at the
initial entry is rare for a Red Teamer or attacker, so it is common to see
lateral movement during an attack.

Let us say a Red Teamer gets a foothold, either remotely or on the network,
within the environment without being noticed as an authenticated user. The next
step would be to seek identities with higher privileges or an identity to
access high-value assets, like data.

Attacks like Kerberoasting are also common since service accounts mainly
have high privileges to services that contain high-value assets. Kerberoasting is also an attack that Defender for
Identity detects. Defender for Identity also detects newer attacks
like PetitPotam as well since version 2.158.14362.

Detection and Response

With Extended Detection
and Response (XDR), Microsoft delivers a new approach to provide intelligent,
automated, and integrated security across domains to help defenders connect
seemingly disparate alerts and get ahead of attackers. Due to signal sharing
between Microsoft Defender for Endpoint and Defender for Identity, an
indicator shows if the endpoint contains an alert within Defender for Endpoint.
An analyst can isolate the endpoint within seconds, and as a Red Teamer, you
will need to find another entry point to continue your journey. The analyst is
also probably more alert and now monitoring the environment even closer as a



2 – an illustration of an attacker navigating a minefield)


Every step we take next as a Red Teamer or
an attacker is like walking in a minefield.


on-premises to the cloud


Although many
organizations go through digital transformation by the increasing their use of
cloud services, attackers can use the on-premises environment as a stepping
stone to the cloud. One of my blog posts describes creating a forged security token to
authenticate to Azure AD using a private key from the AD FS server.
Unfortunately for me, Defender for Identity now detects this method of
attack as well:



(Figure 3 – A
screenshot showing the alert status of an AD FS DKM key read with supporting