If your organisation has been advised to undertake a penetration test, you may be wondering what actually happens during the process. Infrastructure penetration testing is designed to identify vulnerabilities before attackers do, providing a clear picture of how resilient your network really is. For many organisations, the primary focus is Active Directory; the core identity and access management platform that controls users, devices and permissions across the network. That also makes it the single most valuable target on your network. If an attacker gains control of your domain, they effectively control everything: every server, every workstation, every file share, and every account. This is exactly why so much of a modern infrastructure test focuses on it.
Here’s what happens, phase by phase, when SYTECH runs an Active Directory-focused engagement.
- Defining the Scope of the Penetration Testing
Before anyone touches a keyboard against your network, we agree on the boundaries. This is where we establish what’s in scope (which IP ranges, domains, and hosts), what’s explicitly off-limits, when testing will take place, and who to contact if something unexpected happens.
For Active Directory engagements, we’ll also discuss the starting position. Do we begin as an outsider with no credentials, simulating an attacker who has just landed on your network? Or do we start with a standard low-privileged user account, simulating a compromised employee or a malicious insider? Both tell you something different, and the right choice depends on the questions you’re trying to answer.
This phase sounds like paperwork, but it’s what keeps the test safe, legal, and aligned with your actual risk concerns.
- Network Discovery and Reconnaissance
Once testing begins, the first job is simply to understand what’s there. We identify which hosts are alive, which services they’re running, and how the environment is laid out. Domain controllers, file servers, web applications, databases, and legacy systems all get mapped out.
This stage is quiet and non-intrusive by design. We’re building an accurate picture of your attack surface, the same picture a patient, well-resourced attacker would build before making a move. Often, this phase alone surfaces useful findings such as forgotten servers, unexpected services exposed to the wrong network segment, or computer devices that everyone assumed had been decommissioned years ago.
- Active Directory Enumeration
After we have mapped out the landscape, we look at what an attacker can learn and do without any valid credentials. Active Directory environments are surprisingly talkative when misconfigured.
We check whether anonymous or guest access reveals information it shouldn’t, user lists, group memberships, network shares, or password policies. We look for accounts that are configured in ways that let an attacker request crackable authentication material without ever logging in. Two well-known weaknesses fall into this category: AS-REP roasting (which targets accounts that don’t require Kerberos pre-authentication) and Kerberoasting (which targets service accounts). Where those weaknesses exist, we demonstrate them so you can see exactly which accounts are affected and why they matter.
The goal here is to prove which of these theoretical weaknesses are actually present and exploitable in your environment, rather than leaving you to guess.
- Gaining Initial Access
If we can turn any of the above into a valid set of credentials or access to a system, that becomes our foothold. This mirrors how real breaches unfold, rarely a single dramatic exploit, more often a chain of small oversights that add up.
From an authenticated position, the environment opens up considerably. We can now enumerate the domain in far more detail users, groups, computers, trust relationships, and the permissions that connect them all together.
- Privilege Escalation and Lateral Movement
This is where AD testing becomes genuinely distinctive. Active Directory isn’t just a list of users and passwords; it’s configurations and permissions. The vast majority of the engagements I have been involved in, have brought up misconfigurations which lead to sensitive data exposure or account takeovers.
Using established analysis techniques, we map how one account’s access could lead to another’s, and how a chain of seemingly minor permissions can end with control of the entire domain. A helpdesk group with the ability to reset a particular user’s password, an over-privileged service account, a workstation where a domain admin recently logged in, individually these look harmless. Chained together, they can form a direct route from an ordinary user to complete domain compromise.
We move laterally between systems and escalate privileges where the environment allows it, always documenting each step.
- Demonstrating Business Impact
The point of reaching high privilege demonstrates business impact in terms leadership can understand. Once we’ve shown the extent of the access achievable, we illustrate what it would mean in practice which could be access to sensitive data, the ability to disrupt operations, or the capacity to deploy something like ransomware across the estate.
We do this carefully and within the agreed rules of engagement. We’re proving the risk is real, not causing harm to your live systems.
- Penetration Test Reporting and Remediation
The test itself is only half the value. The deliverable is a report written to be genuinely useful to two different audiences.
For your technical teams, there’s detailed, reproducible evidence of every finding, ranked by severity, with clear, prioritised remediation advice, what to fix, and in what order, to break the attack paths we found. For your leadership, there’s an executive summary that explains the business risk without requiring a security background.
The Findings We See Again and Again
Every environment is different, but certain themes come up on the majority of Active Directory engagements:
- Service accounts with weak passwords and far more privilege than they need
- Excessive permissions and unclear group memberships that create hidden attack paths
- Legacy systems and protocols kept alive long after they should have been retired
- Over-exposed file shares containing credentials, configuration files, or sensitive data
- Password policies that look fine on paper but fall apart under real-world cracking
None of these involve fancy coding. Real attackers rely on ordinary misconfigurations, not Hollywood wizardry.
Why It’s Worth Doing
Regular penetration testing is one of the most effective ways to identify weaknesses before they can be exploited by cyber criminals. Whether your organisation needs to meet compliance requirements, reduce cyber risk or gain assurance that critical infrastructure is secure, an Active Directory penetration test provides practical, actionable insight into your security posture.
If you’d like to understand how resilient your Active Directory environment really is, get in touch with the SYTECH team to discuss a penetration test tailored to your organisation, visit https://sytech-consultants.com/contact-us/ or contact 01782 286300.
Common Questions Around Penetration Testing.
What is an Active Directory penetration test?
An Active Directory penetration test assesses the security of your organisation’s identity infrastructure by identifying vulnerabilities, misconfigurations and attack paths that could allow an attacker to compromise your network.
How long does a penetration test take?
The duration depends on the size and complexity of your environment. Smaller engagements may take a few days, while larger enterprise networks can require several weeks, including reporting and remediation advice.
Will a penetration test disrupt business operations?
Professional penetration testing is conducted within agreed rules of engagement to minimise disruption. Testing is carefully planned and monitored to ensure business continuity while accurately assessing security risks.
Why is penetration testing important?
Penetration testing helps organisations identify security weaknesses before cyber criminals do. It provides evidence-based recommendations to strengthen security, reduce cyber risk and support regulatory or compliance requirements.
