Continuous Penetration Testing: How To Lower Costs & Improve Security

Assess and validate your security with PurpleSec’s penetration testing services.

Author: Eva Georgieva / Last Updated: 1/27/2023

Reviewed By: Seth Kimmel, OSCP

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The way that code is developed has changed immensely over the past decade, yet for some reason, companies still believe that implementing security the same way we did it ten years ago should be sufficient.

Think of it this way, we would never purchase tons of different services that we might need as part of our software stack and later ask for their price, yet it is a standard practice to develop all the different features in an application and then ask ourselves if our product is secure.

Implementing continuous penetration testing into your security program in the development cycle from the beginning is not more work. In fact, it enables organizations to develop secure code and discover vulnerabilities more quickly.

Techniques to mitigate these potential breaches can then be developed and implemented across the organization.

As a result of these proactive measures organizations can focus on constantly improving their defensive security controls versus building plans and defenses once the damage is done.

With continuous testing, you are able to receive constant simulations of how a breach can look like, what are your weak points and apply what you’ve learned in your defense strategies.

What Is Continuous Penetration Testing?

There are many definitions of continuous penetration testing. At PurpleSec, we believe conducting a penetration test at least quarterly means you’re continuously assessing your security posture.

There are, of course, many different definitions as to what “continuous” means and which frequency of testing is the best for your organization.

However, at its core, you can say that you are performing continuous penetration testing if your organization is constantly aware of the security status of your application, service, or network system.

When we say “Continuous Penetration Test” we refer to a thorough security assessment with the goal of discovering security flaws in your application, service, or network conducted by an offensive certified security professional (OSCP).

What Continuous Penetration Testing Isn’t

Continuous Penetration Testing does not mean pointing a scanner at an environment or API looking for vulnerabilities. It is also not a checkbox, but a learning opportunity and a mapping tool for the security posture of your environment.

Most importantly, Continuous Penetration Testing is not a barrier in your software development cycle. And this is often something that is quite argued in development teams.

The most frequently asked question once an organization decides to implement continuous penetration testing is:

“How do I fit security in the picture without slowing down the development process?”

The best answer to this is that you can plan it, which puts your organization in control, therefore the development teams communicate better and can address the security challenges in a timeline that works for the organization.

On the other side, by conducting penetration tests only once or twice a year, you are kept in the dark about the security status of your applications, services, or networks for a longer period of time.

This means you can anticipate bigger security issues to be identified, which would then require more work for the development teams, shorter deadlines to implement the newly required security controls, and unavoidable rearrangement of the security development plan.

Why Annual Penetration Testing Isn’t Enough

With the emerging threat landscape, threat actors are constantly on the lookout for zero-day vulnerabilities.

We are experiencing an increasing number of security researchers, new technologies are constantly being developed and implemented in our technology stack and organizations are releasing new features in a more frequent manner.

This just expands the attack surface and accelerates development.

Now the question to ask is “Are you building securely?”, and unfortunately annual penetration tests can’t answer that, and especially not in the pace that things are being built today.

Why Continuous Penetration Testing Is Essential In 2023

With new technologies constantly being developed and AI on the rise, threat actors are now not just using standard tools and methodologies but they are importing AI tools into their arsenal, tools like ChatGPT to build and automate attacks more effectively than before.

In order to combat this growing threat, a more thorough and continuous assessment of your cyber security posture is a must.

The main benefits of continuous penetration testing include:

• Cost-Effective
• Increase Visibility
• Meet Compliance Requirements
• Reduces Cyber Risk

Cost-Effective

You can plan the mitigation of findings, most likely a smaller amount of work will be required therefore not whole teams need to be engaged on fixing the security findings and you can seamlessly implement the fixes as tasks in your sprint. Continuity also allows for better budget planning.

Increases Visibility Of The Security Posture

With continuous penetration testing you are constantly informed about the security status of your environment which gives you more insight into what additional controls need to be implemented in your defense strategy which allows you to continuously and simultaneously build your defense as you assess your posture.

Learn More: How To Improve Visibility In Cyber Security

Helps To Meet Compliance Requirements

Continuous assessments provide more evidence, more findings, and more reports, therefore, removing the pressure of not complying with security standards and regulations since you’ll be constantly up to date.

Reduces The Risk Of Successful Attacks

The key to staying ahead is always data, organizations need to know more about their environment than threat actors do. Continuous penetration testing enables that.

When Should You Consider Continuous Penetration Testing?

An organization can determine when they need continuous penetration testing by evaluating their overall security posture and risk profile.

Some factors that can indicate a need for continuous penetration testing include:

• High-Value Assets: Continuous penetration testing can assist in identifying and resolving vulnerabilities that could be exploited by attackers if an organization has to protect valuable assets, such as sensitive data or vital infrastructure.
• Compliance Requirements: Organizations that work in regulated fields like healthcare or finance may have to adhere to rules that call for frequent penetration testing.
• Frequent Changes To The Network: Continuous penetration testing can assist in identifying and addressing vulnerabilities that may be introduced as a result of network changes on a regular basis.
• Previous Security Incidents: If an organization has experienced security incidents in the past, continuous penetration testing can help identify and remediate vulnerabilities that may have contributed to those incidents.
• Risk Appetite: if an organization has a high-risk appetite, continuous penetration testing will give them the ability to have a more thorough understanding of the organization’s security posture, thus reducing the risk of attacks.

Ultimately, the decision to implement continuous penetration testing should be based on an organization’s overall security goals and risk management strategy.

Best Practices For Implementing Continuous Testing

While you may want to dive right into a continuous penetration testing process it’s important to first explain a few best practices around how to implement this program for your organization.

• Determining The Frequency
• Set Clear Objectives And Goals
• Use Both Manual And Automated Techniques
• Regular Review Of Testing Processes

Determining The Frequency

The frequency in which a pentest should be performed is usually based on how often do you develop new features or make significant changes to our network/codebase/infrastructure and how critical is the new feature that is being developed. Always think of the security implications and the possible worst-case scenarios.

Set Clear Objectives And Goals

Before making the decision to implement continuous security penetration testing answer these questions:

• With what kind of data are we dealing with?
• What are the key flow processes that we want tested?
• What are some scenarios that, if they materialize, would be disastrous for our company?

Write these down and start from there.

It is also quite important to set the communication tone at the beginning of the engagement.

• What is it that you’re looking for from this pentest?
• How can the pentest team help you?

Establish communication channels between both teams so you can get the most value out of it.

Use Both Manual And Automated Techniques

Get an understanding of the methods and techniques that are going to be used throughout the pen test. Look for a service that uses a combination of both manual and automated testing techniques.

For example, automated penetration testing will scan and attempt to exploit vulnerabilities found on the network or application. However, a manual technique is required to identify out-of-the-box security policies set in say Microsoft or security misconfigurations that may be present.

Regular Review Of Testing Processes

The client’s environment changes and so should the testing process. Look for penetration testing services that model APTs using the Mitre ATT&CK framework.

Since you want to collect opinions from both your offensive and defensive teams, it is crucial to establish collaborative threat modeling.

PurpleSec’s Managed Penetration Testing Services

Having a fully managed Penetration Testing solution that integrates directly into your vulnerability management program is the future of offering an enterprise level security solution in a cost effective way.

A managed security provider can offer a range of services. Our managed platform for continuous vulnerability management and testing can improve security by automating many of the manual tasks associated with penetration testing, such as vulnerability scanning and reporting.

This can also significantly reduce the time it takes to complete projects by allowing security teams to focus on more critical tasks, such as remediation and incident response.

The following are some concrete ways a managed platform can increase security and shorten project duration:

• Automated Vulnerability Scanning: Our platform can automatically scan an organization’s systems and networks for vulnerabilities on a regular basis, reducing the need for manual scans.
• Reporting And Analytics: We can provide detailed reporting and analytics on the organization’s security posture, allowing security teams to quickly identify and prioritize vulnerabilities.
• Efficient Remediation: Our model helps security teams more efficiently prioritize and remediate vulnerabilities by providing clear and actionable recommendations for fixing issues.

Affordable Penetration Testing

Another benefit of our offering is that it is not overpriced, but it is designed such that it fulfills your security standards and keeps you on budget.

• The traditional model of an annual pen test starts at $10,000 and is billed upfront.
• The managed model provides quarterly testing starting at $20,000 and billed monthly.

Fully Automated Penetration Test

The effectiveness of your cyber security program is strongly correlated with your capacity to model actual attacks and put in place reliable safeguards to ensure that the same entryway is not used again.

The best way to accomplish that is through automation and we offer that.

Fully automated penetration testing has many advantages for a company.

First, it can considerably cut down on the time and materials needed to carry out a penetration test.

Second, by increasing testing frequency, vulnerabilities may be found and fixed more quickly.

Third, it can deliver repeatable outcomes that are consistent, allowing businesses to spot patterns and trends in their security posture.

Finally, it can be combined with other security technologies to provide a more thorough picture of an organization’s security posture, such as vulnerability scanners.

Performed by Certified Security Experts

PurpleSec cares about people and wants to do security that makes an impact, therefore our team consists of highly experienced professionals.

Our team of cyber security experts have:

• Have direct experience working for the Defense Information Systems Agency, U.S Cyber Command and Other Government agencies.
• Have an average of 20 years of security experience from the C-Level to Technical Implementation and Controls.
• Hold numerous certifications including CISSP, OSCP, CRISC, GCED, GWAPT, MCSE, MCP, CCNA and more.

Integrate With Your Vulnerability Management Program

The mean time to remediation and cyber risk can both be decreased by integrating penetration testing into a vulnerability management program in a number of different ways.

Firstly, by identifying vulnerabilities through penetration testing, an organization can prioritize and address the most critical vulnerabilities first. This can shorten the time it takes to fix vulnerabilities and lessen the likelihood that a cyber attack would succeed.

Second, an organization can better understand the attack pathways and methods that are likely to be utilized against it by incorporating penetration testing as part of the vulnerability management program.

This can assist the company in better understanding its cyber risk profile and determining the best course of action for risk reduction.

Finally, by regularly conducting penetration testing, an organization can track progress in reducing vulnerabilities over time and measure the effectiveness of its vulnerability management program.

This can help the organization to identify areas where additional resources or changes in processes are needed to further reduce cyber risk.

We can help you achieve this by integrating penetration testing into a vulnerability management program to help you reduce the mean time to remediation by identifying and prioritizing critical vulnerabilities, better understand the cyber risk profile and easily track the progress over time.

Wrapping Up

In today’s digital environment, penetration testing is essential because it identifies system vulnerabilities before hostile actors can take advantage of them.

Regular testing guarantees that any flaws are found and fixed right away, shielding the system and its users from potential attacks.

For any organization’s digital assets to remain secure, ongoing penetration testing is crucial.

PurpleSec allows you to build a powerful and continuous penetration testing program.

This allows teams to focus on more important issues and develop programs focused on reducing human error without worrying about the broader threat landscape.