Penetration Testing helps organizations assess the security of their IT infrastructure by proactively exploiting system vulnerabilities the same way an attacker would. Using ethical hacking mechanisms, organizations can simulate an actual attack in a controlled environment, gaining insights into how threat actors infiltrate the system.

By mimicking the actions of a hacker, security teams can patch up open vulnerabilities that can be potentially exploited to destabilize IT infrastructure, thereby improving the organization’s security posture. 

Penetration testing differs from vulnerability assessment as the latter offers a passive security management approach where only potential security flaws are identified. On the other hand, vulnerability assessment tools scan applications, devices, networks & physical IT infrastructure components for potential vulnerabilities and generate detailed reports.

On the other hand, Penetration testing takes this a step further since it involves attempts to compromise and access data from a system safely. As a result, pentests offer a more comprehensive approach to identifying and fixing security flaws in applications than other traditional methods.

This article delves into various benefits, stages, and automated penetration testing tools in modern high-velocity application development. 

Table of contents
  1. How Organizations Undertake Penetration Testing?
  2. What Is Automated Penetration Testing?
  3. The Importance of Automating the Penetration Testing Process
  4. Top Automated Penetration Testing Solutions

How Organizations Undertake Penetration Testing?

Ethical hackers perform penetration tests to check whether a system is secure enough to resist real attacks that can threaten the business. To identify and patch security vulnerabilities before they are exploited, software teams follow a thorough, diligently planned process. The following section explores the various commonly used stages and types of penetration testing.

Stages of the Penetration Testing Process

The penetration testing process begins long before a simulated attack. This allows ethical hackers to study the system, explore its strengths and weaknesses, and identify the right strategies and tools to break into the system. The penetration testing process typically goes through the following five stages:

Planning – This stage involves planning to simulate a malicious attack – the attack is planned in a way that helps to gather as much information on the system as possible. Ethical hackers inspect the system, note the vulnerabilities and how the organization’s tech stack reacts to system breaches. Some methodologies of gathering information include social engineering, dumpster diving, network scanning, and domain registration information retrieval.

Scanning – Based on the finding of the planning phase, penetration testers use scanning tools to explore system weaknesses. This stage identifies the system weaknesses that are potentially exploited for targeted attacks.

Gaining System Access – Having understood the system’s vulnerabilities, pen testers then infiltrate the infrastructure by exploiting security weaknesses. They attempt to exploit the system further by escalating privileges to demonstrate how deep into the target environments they can go.

Persistent Access – This stage identifies the potential impact of a vulnerability exploit by leveraging access privileges. Once they have a foothold in a system, penetration testers should maintain access and hold the simulated attack long enough to accomplish and replicate malicious hackers’ goals. 

Analysis and Reporting – As part of the last stage, the security team prepares a detailed report describing the entire penetration testing process. Some of the details to be analyzed and presented include tools that can successfully penetrate the system, vulnerabilities, and remediation recommendations.

Penetration testing in a graphical representation

Types of Penetration Tests

A typical penetration test involves identifying vulnerabilities that affect an application workflow. To ensure a comprehensive audit, different types of penetration testing cover specific security goals. These include:

External Penetration – These tests target IT infrastructure components that can be accessed from the internet. To do so, these tests are focused on – gaining unauthorized access to web applications, API endpoints, emails, and domain servers to extract valuable information.

Internal Penetration – These tests are performed by security teams simulating an attack by an insider. One of the most common internal manual penetration testing scenarios involves getting into the account of a staff/team member whose credentials are compromised due to a phishing attack.

Blind Penetration – In such tests, the ethical hacker is only given the enterprise’s name whose systems they are testing with no background information. Also known as the closed-box penetration test, this type of penetration test provides software teams with a real-time simulation of how a malicious threat actor gains entry into the system.

Double-blind Penetration – This penetration testing approach simulates an organization’s preparedness for an attack since the security team has no idea whether penetration testing has been appropriately performed. This also means that similar to a real-life attack scenario, security experts have no time to leverage to strengthen their defenses before the data breach.

Targeted Test – A commonly used penetration testing where ethical hackers and security teams work together to keep tabs on each other’s capabilities. Targeted testing offers valuable insights that offer real-time feedback of a hacker’s thought process and next possible exploits.

Run An Automated Pentest and Check for Vulnerabilities


What Is Automated Penetration Testing?

With an increased focus on automation in software engineering, automated penetration testing is an essential approach for easier, reliable, and efficient identification of security gaps and vulnerability exploitation.

These tests can be performed frequently, allowing software teams to keep their security up-to-date, maintain compliance, and retain optimum user experience.

By removing the lengthy and inefficient bottlenecks to perform manual penetration testing, these tools allow software teams to focus on application build rather than spending efforts on implementing security measures or hiring dedicated security professionals. 

An automated penetration testing solution is delivered via a virtual machine or an agent that consistently scans the system for potential flaws. Unlike vulnerability scanners, these tools further filter through the vulnerabilities discovered and choose targets they can use to infiltrate the system.

Automated penetration testers decide on the best targets to use based on such factors as noise and ease of exploitation, among others. Once a target is identified, the software propagates itself through the infrastructure as a human tester would. 

The Importance of Automating the Penetration Testing Process

With automated testing, software security tools imitate attackers’ actions with no human intervention.

In the current technology landscape, an increasing number of organizations are now harnessing the capabilities of Artificial Intelligence and Machine Learning to develop powerful automatic pen-testing tools. While no mature auto-testing platform exists to consider vulnerabilities completely, organizations use available tools for focused areas of vulnerability scanning.

Following are some of the key advantages such tools offer:

Time Benefit

Automatic testing tools perform tests, analysis and produce reports much faster, allowing organizations to detect more vulnerabilities quickly, in near real-time. These tools mostly rely on rules set by Quality Security Assessors (QSAs) to test systems according to PCI security standards to test and analyze application entry points rapidly. Additionally, automated penetration testing tools can run multiple tests simultaneously, reducing the overall time and effort spent.

Integrating Security Testing into CI/CD Pipelines

With Continuous Delivery and Integration being practiced in modern software engineering, human-generated reports may be outdated before delivery. To help solve this, automated testing tools are replicated as frequently as needed, ensuring that security issues in the system are fixed as soon as identified. In addition, this allows development teams to verify the efficiency of components as soon as a change is effected in production.

Easy Learning & Updates 

Human testers require methodical training and a steep learning curve to keep up with the latest developments in the world of cyberattacks. On the other hand, automatic tools are easily updated through over-the-air updates or downloaded scripts to detect newer vulnerabilities or acquire recent pen-testing capabilities.

Enhanced Team Productivity

Auto-testing tools take care of the repetitive and time-consuming tasks of vulnerability scanning, target identification, and privilege escalation. As a result, developers and members of the security teams enjoy reduced stress and improved productivity as they can focus their energy on sophisticated security controls or other tasks that require human intervention. 

Top Automated Penetration Testing Solutions

Automated tools have found favorable use in modern security testing since they use robust, high-quality exploits that simulate a reliable and holistic penetration. Some popular automated penetration testing tools include:

Crashtest Security

Crashtest Security is a popular commercial-grade vulnerability testing suite that offers advanced crawling to detect vulnerabilities within applications. By seamlessly integrating into the application’s development pipeline, Crashtest Security combines high-grade, industry-standard scanning power with a user-friendly interface for efficient web application and API testing. 


This tool is designed to automatically find flaws in modern web applications using proprietary proof-based scanning. The tool plugs into existing tools and workflows, making setup easy and reliable. NetSparker also offers various reporting tools such as a visual dashboard and customizable resources for easy control of data and tracking trends.


Nessus is a popular, comprehensive automated testing tool that implements six-sigma accuracy to ensure deep vulnerability coverage. The tool relies on a simple user interface to make penetration testing simple and intuitive. Nessus includes pre-built templates and policies for simple reporting and analysis and automatically updates plugins for enhanced malware detection. These make the tool suitable for sensitive data searches, compliance checks, and scanning websites & IP Addresses.

Burp Suite Pen Tester

The Burp Suite is designed to improve efficiency in pen-testing by offering full visibility of the system’s comprehensive security exposure. The tool lets organizations combine manual pen-testing techniques with automation for improved speed and efficiency. The suite also consists of several tools that work together to perform the whole pen-testing process, from initial mapping to exploiting vulnerabilities.


Based on the concept of exploit scripts, Metasploit is one of the most popular frameworks for pen-testing. The open-source tool provides a powerful platform to probe weaknesses in the system and understand the motive of a threat attack. The framework integrates seamlessly with other scanning and patch enumeration solutions, making it easy to integrate security assessments into an existing stack.

A recent Cyber observer report suggests that roughly 314 days is the total time it takes from the breach to the containment of a successful cyber attack. It takes an average of 7 months to identify a breach and another 4 months to contain such a breach. The malicious programs deployed by successful hackers are stealthy, automatic, and can successfully disguise themselves as non-malicious files in case of a routine security check-up.

Cyber Observer

Additionally, according to a Cybercrime Magazine’s trend report, by the end of 2021, hacking will cost organizations about $6 trillion. 

Cyber Magazine

Such statistics highlight the severity of the cyberattacks and their potential effects on organizations that rely on technology. To solve this, penetration testing lets organizations stay on top of threats by modeling real-life attacks safely. By continuously simulating attack vectors and providing remediation, automated tools beat conventional penetration testing in modern, high-velocity software pipelines. This accelerates the testing process, allowing vulnerabilities to be identified across all layers and stages of an application workflow. 

To know more about how Crashtest Security can help your organization assess vulnerabilities and safeguard critical application components, sign up here for free and run your first scan.

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