Automated Penetration Testing (APT) Guide

What is automated penetration testing?

Automated penetration testing employs specialized, graph-based software to simulate offensive attack scenarios, discovering and mapping security vulnerabilities across an organizational internal network. 

By adopting an assumed breach mindset and starting from an initial foothold point within the environment, automated penetration testing tools visualize how attackers could exploit interconnected vulnerabilities and misconfigurations to escalate privileges, move laterally, and compromise high-value targets.

Attack path mapping vs. automated pentesting 

As automated penetration testing discovers security vulnerabilities within an organizational network, starting from a domain-joined initial access point, it systematically expands its reach. 

For example, the automated penetration testing software might identify a high-privilege Kerberoastable account with a weak password, crack it offline to obtain the plaintext credential, and leverage that credential to access a new network asset through attack simulations.

With each newly accessed asset, dynamic enumeration techniques run to identify additional targets. As the tool discovers and accesses more assets through offensive TTPs, the attack graph grows progressively larger. 

Figure 1. An example critical attack path leading to a domain admin account 

This way, security teams can prioritize remediation efforts at the most critical choke points, particularly where multiple attack paths converge and could lead to severe consequences.

How does automated penetration testing software work?

Continuous discovery techniques for hidden attack paths

For all offensive security professionals, including black and ethical hackers, enumeration is key to success. Hence, automated penetration testing is no different.

In automated penetration testing, the enumeration process is dynamic, continuous, and concurrent. It maps an organization’s internal network to gather detailed information about resources and configurations. This process goes beyond traditional vulnerability scanners by tracking the relationships between users, devices, and permissions, providing an up-to-date view of the attack surface.

By integrating identity mapping (such as AD objects and ACLs), infrastructure assessments (including policies and configurations), and connectivity insights (like active sessions and domain trusts), data collection uncovers the underlying connections within the network. This process mimics adversarial enumeration behaviors that occur after initial access (e.g., assume breach mindset), ensuring that any new asset or permission change is promptly analyzed for potential attack paths.

Figure 2. Example discovery techniques run in an arbitrary environment with Picus APV

Running offensive MITRE ATT&CK TTPs to gain access to new nodes

An automated penetration testing software dynamically simulates real-world adversarial tactics within an organization's internal network to validate whether security misconfigurations can be chained in high-impact attack paths.

This process mimics attacker behaviors, such as vulnerability exploitation, privilege escalation, credential harvesting, and lateral movement (as shown in Fig. 2), to assess potential risks.

As the simulation progresses, new nodes and systems are accessed, triggering discovery techniques that expand the attack surface. This iterative process provides security teams with a continuous view of potential attack paths, enabling them to prioritize remediation efforts.

Figure 3. Attack techniques for automated penetration testing (Picus APV)

Attack path mapping for better attack graph visualization

Attack path mapping illustrates the possible routes an attacker might take to reach critical assets, expanding dynamically as the threat simulation progresses. As the simulation uncovers new access points, additional discovery techniques are triggered, which in turn leads to further identification of assets and vulnerabilities. 

With each new node accessed, more data is gathered, enriching the map with additional details. 

This makes attack path mapping an integral part of attack path validation, in collaboration with automated penetration testing, evolving alongside the exploitation of vulnerabilities and the application of new access techniques.

Therefore, attack path mapping plays a crucial role in visualizing the progression of an attack.

Figure 4. An example attack path mapping with Picus APV

Risk prioritization for business-critical attack paths

In automated penetration testing, risk prioritization for business-critical attack paths focuses remediation efforts on paths that target high-value assets, such as Domain Admin accounts. 

The priority is placed on attack chains that lead to the compromise of these critical systems, as they pose the highest risk. 

For instance, a chain like Service Enumeration → Modifiable Service Exploitation → Privilege Escalation → LSA Credential Cache Dumping → Password Cracking → Domain Admin is prioritized due to its direct impact on valuable assets. Paths leading to critical targets are ranked higher than those ending at lower-privilege systems. 

Even techniques that appear to be low-risk, like Service Enumeration, become critical when they contribute to an attack path that leads to domain compromise. 

Can penetration testing be fully automated?

It's crucial for understanding the true value of automated penetration testing to answer this question. 

While automated penetration testing software can handle sophisticated tactics that surpass the abilities of a mid-level red teamer, they still can't replicate the creative and strategic thinking of a senior red teamer. 

• For mature red teams, automating repetitive tasks allows experts to focus on more complex, creative aspects of testing. 
• For organizations with developing red teaming capabilities, automated penetration testing offers a long-term solution, helping build a more robust security framework and enabling growth toward more advanced capabilities. 

This difference highlights how automation can complement, rather than replace, the human touch in cybersecurity.

How does automated penetration testing compare to traditional manual testing?

Organizations achieve optimal security posture by combining both methodologies: automated testing for continuous validation and comprehensive attack path mapping, with periodic manual assessments for deep-dive analysis of critical systems and business-specific vulnerabilities.

Key differences: automated pentesting vs. manual penetration testing

Black box testing vs. white box testing in automated pen testing tools

• Black box testing treats the environment as unknown. The tool has no internal visibility and relies on external discovery and probing to find weaknesses. This limits depth, slows progress, and often proves only that a vulnerability exists, without showing how far an attacker can realistically go.
  
• White box testing in automated penetration testing operates with full visibility into the environment, including assets, configurations, and credentials when appropriate. Testing typically starts from a domain-joined account, representing an attacker who already has internal access to the network. This approach allows automated tools to validate which internal exposures are truly exploitable, track lateral movement step by step, and map complete attack paths to critical objectives. The result is broader coverage, deeper validation, and a more accurate understanding of real security risk.

In automated penetration testing, white box testing provides more complete, reliable, and actionable outcomes because it reflects how attacks unfold once an adversary is inside the network.

Automated penetration testing for internal penetration testing needs

Automated penetration testing for internal penetration testing starts from a domain-joined account (as stressed earlier) inside the network, deliberately assuming the attacker already has a foothold. 

Hence, it is not black-box testing; it perfectly mirrors post-compromise attacker behaviors observed in real intrusions.

From the initial access point, the tool performs continuous and adaptive discovery, running sophisticated enumeration techniques (like Windows Active Directory enum.) to map users, groups, services, permissions, trusts, and policies. 

Enumeration is central because attackers can only move as far as their visibility allows. As new information is uncovered, the testing logic adapts in real time.

Figure 5. Initial access point for white-box internal automated penetration testing with Picus APV

When exploitable conditions emerge, such as a Kerberos-enabled account combined with weak credentials, the tool validates whether that condition can be abused. If credentials are successfully cracked offline and access shifts from one identity to another, discovery immediately resumes from this new security context. With higher privileges, previously hidden assets, relationships, and attack paths become visible.

This process repeats as access is gained through credential abuse, privilege escalation, lateral movement, or vulnerability exploitation. 

Each newly accessed node triggers further enumeration, causing the attack path map to expand dynamically and concurrently, just as it would during a real attack.

Crucially, this approach is goal-driven and stealthy, not noisy or exhaustive. The tool does not attempt to compromise every system. Instead, it prioritizes privilege escalation and traversal toward high-value targets like Domain Admin, reflecting how real attackers conserve access, minimize exposure, and focus on outcomes.

The result is a highly realistic internal penetration test that answers a critical question: 

If a specific user account is compromised, what paths can an attacker actually take from there? By testing from any internal starting point, teams can understand real blast radius, validate exploitability, and identify the attack paths that truly matter.

Can autonomous pentesting be used for insider threats?

Yes. Autonomous pentesting can be used to model insider-threat and disgruntled employee scenarios by starting from legitimate internal user accounts and simulating how abuse of access, misconfigurations, and credential weaknesses can be chained to escalate privileges or access sensitive assets.

Rather than detecting malicious intent, it answers a practical question: what damage could a compromised or misused internal account realistically cause, and which paths lead to high-impact outcomes such as domain admin access or sensitive data exposure.

How does automated penetration testing support a Zero Trust architecture?

Automated penetration testing supports Zero Trust by continuously validating whether trust boundaries, access controls, and privilege assignments actually prevent attacker progression under real attack conditions. 

By executing full attack chains, spanning discovery, privilege escalation, credential abuse, and lateral movement, it exposes where implicit trust still exists between users, systems, and services. This allows security teams to identify and eliminate hidden access paths that violate Zero Trust principles, ensuring that least privilege, segmentation, and access policies are enforced not just by design, but in real-world adversarial scenarios.

Practical use cases for automated penetration testing tools

• Simulates real-world adversary tactics to identify exploitable vulnerabilities and misconfigurations within an organization’s network. This continuous testing process helps security teams discover critical security gaps, prioritize remediation efforts, and reduce the risk of exploitation by attackers.
• Improves ransomware readiness by identifying and prioritizing attack paths that lead to Domain Admin access, allowing security teams to block the privilege escalation and lateral movement steps ransomware operators rely on before encryption or mass deployment occurs.
• Runs real-world, sophisticated attack techniques like an in-house red teamer, such as privilege escalation, lateral movement, credential brute-forcing, and data exfiltration, to assess the security of systems and networks.
• Determines which files and data repositories an attacker could realistically locate and exfiltrate once inside the environment.
• Automatically uncovers misconfigurations, weak security policies, trust relationships, and exposed credentials that could be leveraged by attackers.
• Continuously evaluates internal access, permissions, and trust relationships to detect insider-driven risk and security drift caused by changes in the environment.
• Automates the identification of the most critical attack paths, helping security teams focus on high-risk exposures that could lead to significant breaches.
• Continuously tests for security weaknesses, minimizing the window of opportunity for attackers to exploit vulnerabilities.
• Supports compliance with regulatory frameworks like DORA, PCI DSS, and ISO 27001 by automating vulnerability assessments and ensuring organizations remain audit-ready.
• Operates autonomously, executing tests and simulations without requiring manual approval, ensuring rapid response to newly discovered vulnerabilities.
• By providing continuous, automated validation of security controls and attack surfaces, automated penetration testing helps organizations stay ahead of threats, reduce risks, and maintain a proactive security posture while ensuring compliance.
• Reduces attacker dwell time by continuously validating detection and containment paths, allowing security teams to identify where adversaries could move undetected and close those gaps before exploitation occurs.
• Delivers clear, outcome-driven penetration testing reporting for CISOs, boards, and decision-makers by translating technical findings into business-impact scenarios, such as domain compromise, ransomware risk, or data exposure.

How to choose the best automated penetration testing tool for you? 

Here are the key questions you need to ask before choosing the best automated penetration testing tool for your organization:

• Assumed-breach starting point: Can it start from a domain-joined user or internal asset and realistically model post-compromise attacker behavior?
• Real exploit validation: Does it execute attack techniques to confirm what is actually exploitable, rather than stopping at exposure discovery?
• Attack path mapping and prioritization: Can it chain findings into full attack paths and clearly show which paths lead to Domain Admin, data exfiltration, or ransomware?
• Dynamic enumeration and adaptation: Does it continuously re-enumerate users, permissions, trusts, and assets as access changes, reflecting real attacker progression?
• Continuous and autonomous operation: Can it run safely on a schedule or autonomously without manual approvals, keeping pace with a changing environment?
• Outcome-driven reporting: Does it translate technical results into business-impact outcomes that CISOs, boards, and decision-makers can act on?
• Zero Trust and insider-risk validation: Can it expose hidden trust relationships and show how legitimate access could be abused to escalate privileges?
• Choke-point identification: Does it highlight where fixing a single weakness breaks multiple attack paths, maximizing remediation impact?

What is the best automated penetration testing solution for meeting security compliance requirements?

The best automated penetration testing solution for meeting security compliance requirements is one that goes beyond checkbox testing and continuously validates real exploitability in your environment. 

It should operate with an assumed-breach mindset, execute realistic attacker behaviors, and map attack paths to critical assets so you can demonstrate not just that controls exist, but that they actually prevent privilege escalation, lateral movement, data exfiltration, and ransomware impact.

From a compliance perspective (PCI DSS, ISO 27001, DORA, SOC 2, GDPR, HIPAA), the strongest solutions provide continuous evidence, outcome-driven reporting, and clear remediation prioritization tied to business risk. This allows security teams to stay audit-ready at all times while giving auditors and decision-makers defensible proof that security controls are actively tested, effective, and maintained in dynamic environments.

What does Gartner say about automated penetration testing software?

In alignment with this, on November 8, Gartner published a report titled “How to Grow Vulnerability Management Into Exposure Management,” which highlights that the following technologies and practices have been integrated into the broader category of Adversarial Exposure Validation. 

• Breach and Attack Simulation (BAS): Simulates attacker techniques to identify vulnerabilities and test security controls effectively without the need for a live attack.
• Automated Penetration Testing: Leverages automation to simulate real-world attack scenarios, identifying weaknesses and potential attack paths in an efficient and scalable manner.
• Attack Path Mapping: Visualizes potential attack paths, highlighting key vulnerabilities and showing how an attacker might navigate the environment to achieve their objectives.

Continuous automated penetration testing with Picus

As emphasized earlier, Automated Penetration Testing and Attack Path Mapping technologies provide security teams with accurate, risk-free, and continuous testing. 

Within Picus Attack Path Validation (APV), these capabilities are offered together to deliver unparalleled efficiency, minimizing network disruptions and reducing the time security operations teams spend on manual research. APV not only identifies critical risks but also maps actionable next steps to address them promptly, empowering teams to prioritize and remediate threats effectively.

Figure 7. Automated Pentesting and Attack Path Mapping to Achieve an Attacker’s Objective

The benefits of utilizing Picus Attack Path Validation (APV) are outlined below. If you prefer to dive straight into the case study, feel free to skip this brief section and proceed to the next title.

• Accurate and Stealthy Approach: Using a stable and evasive approach to testing, which can be initiated from any point within the network, we offer a stealthy solution that mimics real-world attackers. Picus APV delivers more accurate threat scenarios and attack paths with less false positives even in large network environments. 
• Risk-free: minimize the risk of unintended disruptions with the ability to prioritize operational stability. With streamlined and secure testing you can safeguard critical systems without manual approvals.
• Continuous and Autonomous: schedule and run assessments in parallel to keep up with your environment. Additionally, once configured APV can run on auto-pilot and automatically initiate and execute simulations continuously without requiring approvals for each exploit attempt. 

In addition, when combined with Picus Breach and Attack Simulation security teams can benefit from a comprehensive approach to Adversarial Exposure Validation, as they work to improve their security posture.  

Customer Testimonial for Automated Penetration Testing with Picus APV

In the previous section, we explored the capabilities of Picus APV and walked through a step-by-step case study of running a simulation with the platform. Now, let’s hear directly from one of our customers about how Picus APV has transformed their security operations.

This testimonial underscores the real-world value Picus APV delivers to organizations, helping them stay ahead of evolving threats while strengthening their security posture through automation and adaptability.

Picus APV Pricing:

Flexible Solutions for Realistic Automated Pentesting Simulations

For Picus Attack Path Validation (APV), our pricing is based on the number of hosts in the environment. This means that as the size of the environment increases, the number of host licenses required, and consequently the cost, also increases. 

However, we understand that some clients may prefer to start with a smaller scope to evaluate the solution. In such cases, we offer the flexibility to initiate the APV process by selecting a limited number of hosts randomly. This approach allows the client to experience the solution's capabilities without committing to a full-scale deployment upfront.

To get a better understanding, click here to get a demo.

See How an Attacker Can Reach Domain Admin in 7 Steps