The Complete Guide to Understanding Automated Penetration Testing

What Is Automated Penetration Testing?

In this section, we will provide the true definition of automated penetration testing, explain how it works, demonstrate how it simulates adversarial behaviors after a breach, and outline the attack techniques it employs.

Definition of Automated Penetration Testing

Automated penetration testing is the use of specialized software to identify security weaknesses and misconfigurations within an organization's environment. Examples include Kerberoastable accounts, weak password policies, and the exploitation of known protocol vulnerabilities such as SMB, as well as credential dumping attacks. 

This method adopts an adversarial perspective, uncovering and chaining seemingly isolated vulnerabilities to access critical organizational assets, such as domain admin accounts—effectively mimicking real-world attack scenarios.

How Does Automated Pentesting Work?

Before discussing the flow of an automated penetration testing simulation, it is essential to understand that these technologies are developed with a specific mindset: the assumption of a breach.

Automated Pentesting Assumes a Breach Has Already Occurred

Automated penetration testing solutions are specifically designed to simulate what happens after a breach, focusing on scenarios triggered from a domain-involved host. This approach mimics the initial foothold of an attacker who has gained access to a host within your domain, such as through the compromise of an endpoint or the exploitation of an internet-facing application via a specific CVE. These simulations do not assume an internal breach but start from the entry point, providing a realistic view of potential attack paths that adversaries could take from the breached domain asset.

How Attacks Are Executed in an Automated Pentesting Simulation

The automated penetration testing process begins with discovery actions to map accessible assets within reach of the compromised host (a.k.a. patient-zero from which the simulation is triggered). Stealthy credential access attacks are then executed to avoid alerting implemented security controls, mimicking the behavior of sophisticated attackers. If successful, the tool leverages the obtained credentials to escalate privileges further. These escalated privileges enable lateral movement to other hosts along the attack path, ultimately progressing toward high-value targets such as a domain admin account. (To see a step-by-step case study of an automated penetration testing simulation, refer to the Continuous Automated Penetration and Attack Testing with Picus section.)

Through this approach, automated penetration testing provides a comprehensive and realistic view of potential vulnerabilities, demonstrating the attacker’s journey and highlighting critical weaknesses that need remediation.

A Comparison Guide to Penetration Testing: Manual vs. Automated 

This section compares manual penetration testing with automated penetration testing simulations across four main categories: scope and depth, cost and resource allocation, accuracy and depth, and frequency and scalability.

1. Scope and Depth: Automation Brings Broader Coverage to Pentesting 

Manual Penetration Testing: Offers an in-depth, tailored analysis, focusing on complex and business-specific vulnerabilities. Highly effective for uncovering edge-case scenarios and providing detailed insights that require human expertise.

Automated Penetration Testing: Offers broad coverage of the attack surface, identifying security vulnerabilities and misconfigurations efficiently. By leveraging AI-driven intelligence, it maps stealthy attack paths and validates each step, ensuring accurate and comprehensive results, ideal for large and dynamic environments.

2. Cost and Resource Allocation: Striking a Balance Between Investment and Value

Manual Penetration Testing: Resource-intensive and typically more costly due to the reliance on skilled professionals. Additionally, manual testing often involves aggressive probing techniques that can place significant stress on the network, as it focuses on uncovering vulnerabilities without prioritizing stealth or minimizing impact.

Automated Penetration Testing: Streamlines the discovery and validation of attack paths, minimizing reliance on manual effort while acting as a skillful real-life hacker.

3. Accuracy and Depth: Tailored Insights vs. Systematic Detection

Manual Penetration Testing: Renowned for its precision in identifying business logic vulnerabilities and complex attack chains. Human testers excel at contextual analysis and simulating realistic, nuanced attack scenarios, reducing false positives and uncovering issues unique to specific environments. 

Automated Penetration Testing: With automated solutions, you can initiate a penetration testing simulation from any desired host, providing unmatched flexibility and coverage. These simulations reveal the stealthiest and most critical attack paths to high-value objectives, such as domain admin account access.

4. Frequency and Scalability: Meeting the Needs of Dynamic Environments

Manual Penetration Testing: Conducted infrequently due to high costs and time demands, it is best suited for targeted assessments during critical stages like deployments or compliance audits. Its resource-heavy nature makes it less practical for addressing rapidly changing attack surfaces or conducting continuous testing.

Automated Penetration Testing: Automated solutions provide continuous, scalable assessments, adapting to dynamic IT environments. By simulating real-world attack scenarios from any host at any time, they uncover critical attack paths and deliver real-time insights, enabling security teams to proactively address emerging threats and maintain a strong security posture.

Three Reasons Automated Penetration Testing Helps CISOs Sleep Better at Night

Adversarial behaviors are reaching an unprecedented level of sophistication, further compounded by the rapid expansion of digital ecosystems driven by cloud adoption, remote work environments, SaaS applications, and interconnected operational technologies. Caught between increasing attack campaigns, complex IT environments, and limited resources for security teams and tools, decision-makers are seeking solutions to protect their organizations from highly destructive breaches.

Reason 1. Attack Path Mapping Shows What Happens After Your Employee Clicked on a Phishing Link

With the advancements in LLM (Large Language Model) technologies, adversaries are becoming increasingly proficient at crafting spear-phishing campaigns targeting employees to gain footholds in organizations' internal networks. They often remain undetected for months due to their stealthy lateral movement techniques and ability to exploit seemingly isolated security weaknesses. 

This has become a persistent challenge that keeps CISOs awake at night. To address this, Automated Penetration Testing and Attack Mapping capabilities are being increasingly adopted by Adversarial Exposure Validation (AEV) vendors. 

These Automated Pentesting and Attack Path Mapping technologies map out your internal network from any chosen starting point and mimic the actions of a real-life sophisticated hacker, revealing the stealthiest attack paths leading to your organization's crown jewels, such as domain admin accounts. 

By demonstrating how security vulnerabilities—such as Kerberoastable accounts or weak password policies in HR—can be exploited and chained by an adversary to deliver maximum impact, your security team gains a data-driven visualization of the issues that require immediate attention. This proactive approach addresses the question, "What happens if an employee clicks on a phishing email?" and helps eliminate strategic vulnerabilities that adversaries could exploit to move laterally within your environment.

Reason 2. Pentesting Automation Helps Your Security Team in a Dynamic Attack Surface

Organizations today face an increasingly complex challenge: their attack surfaces are expanding rapidly, making it difficult to keep up with emerging exposures. Traditional solutions like vulnerability management tools, while adept at identifying known software and application vulnerabilities, inherently lack the capability to uncover misconfigured security controls, weak baselines, exposed credentials, or admin accounts with poor password hygiene. These gaps leave organizations vulnerable to threats that often go undetected.

While manual pentesting remains invaluable, its resource-intensive nature often limits engagements to once or twice a year, leaving gaps in a constantly evolving IT environment. Automated pentesting solutions serve as the ideal complement to manual efforts. By providing continuous testing and real-time insights into newly emerging exposures, they ensure organizations remain agile and prepared. Automated solutions won’t replace the depth of manual testing but offer a proactive layer of security that lets CISOs sleep better at night, knowing their defenses are continuously validated.

Reason 3: Automated Pentesting for Adherence to Compliance and Regulatory Standards

Automated penetration testing supports compliance by providing continuous assessments of security controls, ensuring adherence to frameworks like DORA, PCI DSS and ISO 27001. Unlike manual testing, which is periodic and resource-intensive, automated solutions deliver consistent visibility into vulnerabilities, allowing organizations to address issues promptly and stay audit-ready. 

For CISOs, this means confidence in their organization's ability to meet regulatory demands and mitigate risks effectively. The reassurance of ongoing compliance validation allows CISOs to sleep better, knowing their security posture is proactively managed.

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. 

These advancements enable the validation of identified exposures within an organization’s unique IT environment, assign contextual risk scores based on the findings, and facilitate more effective prioritization of remediation efforts.

• 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.

In the upcoming section, we will showcase not only our Security Control Validation (SCV) product, powered by our pioneering Breach and Attack Simulation technology, but also how Picus Attack Path Validation uniquely combines the capabilities of Automated Penetration Testing and Attack Path Mapping. 

Together, we’ll explore a step-by-step case study to demonstrate the execution and impact of an APV simulation.

Continuous Automated Penetration Testing Simulation 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 1. 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.  

Step-by-Step Case Study: Running an Automated Pentesting Simulation with Picus APV

In this section, we will provide a step-by-step explanation of how to run an automated penetration testing simulation using Picus Attack Path Validation (APV).

Step 1:

Choosing the Objective of an Automated Pentesting Simulation

Good automated penetration testing solutions must focus on objective-based simulations to mirror real-world adversarial tactics effectively. Since adversaries always act with a clear goal—be it encrypting sensitive data, exfiltrating information, or gaining control of critical systems—it is essential for these tools to replicate such purposeful behaviors to assess vulnerabilities comprehensively. 

Picus exemplifies this approach by providing targeted simulation objectives, such as 

• Simulating Ransomware Behavior, to test data protection and exfiltration defenses, and 

• Obtaining Domain Admin Privileges, to evaluate the security of privileged access within Active Directory environments. 

These options enable organizations to measure their resilience against the most impactful threats.

Figure 2. Choosing the Objective for the Automated Pentesting Simulation with Picus

For this case study, we will focus on the objective of obtaining domain administrator privileges within an Active Directory environment. This goal represents a critical milestone for adversaries, as achieving domain admin access provides complete control over the network, enabling lateral movement, data exfiltration, and potentially crippling disruptions. By simulating this scenario, we aim to demonstrate the vulnerabilities that attackers exploit and the importance of implementing robust security controls to prevent, detect, and mitigate such high-impact threats.

Step 2:

Choosing the Attack Actions for Pentesting Simulations

In the following step, we are going to choose which attack actions we will allow the Picus APV used in our environment. Actions are listed under four different categories:

• Discovery

• Credential Access

• Privilege Escalation

• Lateral Movement

Clicking on each category, we can select or deselect the attack vectors we want Picus APV to run. Below, you can see a screenshot from Picus APV’s Credential Access section, which lists some of the actions within this category.

Figure 3. Choosing the Attack Actions for the Automated Pentesting Simulation with Picus

It is important to note that just because you are choosing a certain attack action does not mean that Picus Intelligent Adversary Decision Engine is going to blindly try these on every endpoint in your environment. It is quite the opposite.

Step 3:

Defining the Scope of Pentesting Testing Simulation

Scoping is a critical step in penetration testing, whether traditional or automated, as it ensures simulations focus on relevant assets. The following screenshot illustrates how Picus APV enables users to define target device restrictions by specifying domain names, IPs, or ranges. This flexibility allows organizations to tailor simulations to their unique environments, ensuring lateral movement paths are accurately assessed and critical assets are prioritized.

Figure 4. Deciding the Scoping for Picus APV Simulation

After the scope of the pentesting simulation is decided, it is to move onto the next step: downloading the initial stager.

Step 4:

Downloading the Initial Stager to as a Starting Point for Our Simulation

In this step, we will select and download the initial stager to begin the simulation. The choice of stager does not limit the simulation path, as alternative stagers are available. Depending on your desired execution method, implementation process, file type, or compatibility with tested EDR vendors, you can select the stager that best fits your requirements.

Refer to the table above to explore the available stagers, such as the Honeybadger Stager and Eagle Stager, each offering different execution methods (e.g., APC Injection or Callback Functions), implant processes (e.g., Remote or Self-Hosting), and file types (e.g., EXE or DLL). This flexibility allows you to tailor the simulation to your specific needs and environment.

Figure 5. Downloading the Initial Stager to Trigger the Pentesting Simulation

Step 5:

Analyzing the Pentesting Simulation Results

After the simulation is completed, it's time to analyze the results. The process begins with a simulation summary, which confirms that the objective was successfully achieved: obtaining the NTLM hash of the ADMIN user, who has admin-level privileges, within 27 minutes.

The summary provides additional details, but for demonstration purposes, we focus on the attack path mapping generated by the simulation. This map can be explored in detail, with zoomable micro-components on the left. On the right, we see the activity feed, which logs all actions performed during the simulation.

For instance, in the left pane, we observe that Picus APV executed code over the SMB protocol to successfully perform lateral movement to DB02, a database within our tested environment. The corresponding card includes a note indicating that a new session was established on this asset using the administrator user.

Figure 6. Attack Path Mapping for Automated Pentesting Simulation with Picus APV

Remember the attack actions we allowed at the start of our simulation. Here, the Picus Intelligent Adversary Decision Engine generates this comprehensive mapping by performing various attack actions on the hosts it reaches in the most stealthy way possible. When an action succeeds, it proceeds to the next host.

On the map, you’ll notice that some hosts are tested after others, but only one may be successfully used for lateral movement. This reflects the realistic nature of actual IT environments and serves as proof that the Picus Intelligent Adversary Decision Engine operates like a real-life hacker, finding the most efficient and stealthy route to its objective.

If the attack path mapping seems too detailed to analyze, you can directly focus on the specific attack path that led Picus APV to the domain admin account.

Figure 7. The Attack Path Leading to Domain Admin Account

Note that Picus APV not only identifies the security weaknesses in your hosts that adversaries could exploit to reach a domain admin account, but it also provides a detailed mitigation guide for addressing these vulnerabilities. For example, it might reveal the presence of a Kerberoastable account while simultaneously offering actionable recommendations, such as implementing complex password generation and enforcement.

This means the product goes beyond merely mapping potential attack paths; it ensures you receive actionable guidance to enhance your security posture. Moreover, we continuously work to improve and expand this guidance to deliver even greater value.

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.

Open Source Automated Penetration Testing Tools

While our discussion has primarily focused on commercial automated penetration testing solutions, several open-source tools are available that offer valuable capabilities:

• Metasploit: A widely-used framework that facilitates comprehensive penetration testing through a user-friendly interface. 

• OpenVAS: A free tool offering advanced vulnerability scanning within its own framework. 

• Burp Suite Community Edition: An open-source version of the Burp Suite platform, providing essential tools for web application security testing. 

• Nikto: A free, open-source web server scanner designed for comprehensive testing against various vulnerabilities. 

• Nmap: A network exploration tool and security scanner used to identify open ports and services on a network. 

• SQLmap: An open-source tool that automates the detection and exploitation of SQL injection flaws. 

While these tools provide valuable insights, they can generate a significant number of false positives. Interpreting these results often requires dedicated professionals to distinguish between genuine vulnerabilities and false alarms, which can diminish the inherent advantages of automated penetration testing.

Therefore, it's imperative for organizations to not only identify their vulnerabilities but also assess the business-critical risks associated.