Leading a global penetration testing practice several years ago I found that most organizations that planned their needs last minute were meeting compliance that they didn’t know was needed or required with a partner, with a few clients who cared more about security, and then a select few that were optimizing to the left of boom to reduce risk continually in operations. Is automated penetration testing for you? How do you know? When and how do you get into this marketplace if you’re not a pen testing expert but may need such services, continually?
Don’t Go It Alone
Living in the Pacific Northwest we realize that the folks that successfully navigated the Oregon Trail had a guide. Someone that had been on the long and treacherous road before them, that knew the way, the tactics, and what really mattered and didn’t, for success. If you’re new to penetration testing and security beyond compliance start by hiring an external third-party expert to guide, you along the way. You won’t regret having a trusted 3rd party like 4D5A Security who helps you identify needs, priorities, your best return on investment strategy and roadmap, and how to best implement for success when learning new skills, tools and operations.
Why Automated Pen Testing?
Traditional penetration testing is human based, expensive, and time consuming. As a result, it is often done annually or whenever it is required, and not much more often. Change management and realities of dynamic ever-changing networks and assets are mean while vulnerable to attack until they are tested and validated at a single point in time a year later.
Automated penetration testing can also baseline and consistently test with known trusted results compared to varied human penetration testers with various levels of skills, ability, and focus. This is especially true in 2025 where there is an entire new generation of “tools-based” penetration testers that just run tools and don’t really have architectural knowledge, or techniques, tactics, and procedures (TTPs) to hack beyond the tool, where the tool often does a better job than low skilled penetration tester behind the tool. Modern tools now use AI to learn and become more effective and capable over time within an environment, improving value each day it is used in production.
Some of the chief benefits of automated penetration testing are listed below to summarize key areas of application and risk reduction, when properly configured, deployed, and used in operations:
- Exposure Management (EM)
- Cyber Asset Attack Surface Management (CAASM)
- Digital Forensics & Incident Response (DFIR)
- Breach and Attack Simulation
- Managed SIEM Services
- Vulnerability Prioritization (Threat and Vulnerability Management/TVM)
- Network Detection & Response (NDR)
- Endpoint Detection & Response (EDR)
- Bot Management
- Application Security Posture Management/Secure Coding by Design
- API Threat Protection
- Threat Modeling Automation
- Cloud Web & API (Cloud WAAP)
- Mobile Application Security Testing
- Artificial Intelligence Security Testing (AI Security)
In summary, each layer of operations and architecture are now able to be supported by continual penetration testing to reduce risk proactively to the left of boom and in real-time, as changes are made and rapidly detected.
The Good, The Bad, and the Ugly
Not all tools are made the same and some of the features don’t work as advertised – sorry to speak truth here! Overall, the market has matured significantly over the past few years with a few leaders that have solid products and solutions with improving support and features. Initially, a few years ago, support was person-based and ad-hoc, remote support and access was ‘initial’ and immature for some solutions, and setup was too cumbersome out of the box for such an as-a-service solution.
Startups in the space have matured significantly and have continued to mature with feature request development and roadmap additions that continue to drive value towards enablement of continual penetration testing and security within your own organization, affordably, to reduce risk.
“Wins” in the space now sound like this:
- Getting to Your Repos Before Attackers
- Using KEV & AI to Stay Ahead of Attackers
- I See Changes in Real Time and Remediate
You’ll still need humans – despite how automation helps – to solve more complex, architectural, and operational needs within the organization. Automated penetration tools drive consistent, efficient, real-time risk reduction to the left of boom empowering your staff to focus on what they do best instead of being too busy to have the visibility or manage it.
When Am I Ready?
If you’re already penetration testing on a regular repeated basis and understand the value and are compliant you appreciate the marketplace, outcomes, and the lifecycle of penetration testing, remediation, and how to best manage all that is involved with this service. This enables leadership to make an informed decision, with the help of an expert third party and roadmap, towards how to best onboard, implement, and scale over time automated penetration testing for continual risk reduction in operations. You’ll already have a budget for annual penetration testing and can adapt it towards an automated penetration testing solution, showing increased value and return on investment for the organization, with continual testing. Ensure the right staff exist and have training to properly configure, run, and consume automated penetration testing tooling, reports, and remediation to drive operational outcomes required for the program to be a success.
