Beyond Compliance: How to Effectively Plan Your Offensive Security Engagement
Why Planning Your Offensive Security Engagement Matters
When it comes to offensive security, many organizations start with one goal: meeting compliance requirements. And while compliance is important, it often leads to a check-the-box approach where security testing is done just to satisfy regulators rather than to uncover real security risks.
The problem? Many companies don’t have a clear vision of what they actually want to achieve with an offensive security engagement. They know they need to test something, but they’re unsure what the focus should be, what’s most critical, or how the results should drive security improvements. This often leads to engaging a service provider just to run tests, generate a report, and move on without truly understanding what was tested or how it impacts the organization’s overall security.
A big reason for this is the lack of structured planning. Even when companies fill out scoping forms provided by service providers, they often don’t provide enough useful details leaving providers to make assumptions about what needs to be tested. Without clarity on priorities, threat models, or risk appetite, the engagement might end up missing key security gaps or focusing on the wrong areas.
This blog is here to change that. If your organization is planning an offensive security engagement, you should be asking:
- What are we trying to achieve beyond compliance?
- What systems, applications, or attack vectors do we need to focus on?
- What type of testing is best suited for our risk profile?
- How do we measure success beyond just getting a report?
By thinking beyond compliance and planning with clear objectives, companies can ensure that offensive security isn’t just an exercise in paperwork it becomes a valuable tool for identifying real risks, improving defenses, and strengthening overall cybersecurity resilience.
Why Companies Need Offensive Security
Cyber threats are constantly evolving, and attackers are becoming more sophisticated in how they target businesses. Yet, many organizations only realize their security weaknesses after a breach has already happened. This reactive approach often results in financial losses, reputational damage, and regulatory penalties all of which could have been avoided with a proactive offensive security strategy.
Why Is Offensive Security Important?
Unlike traditional security measures that focus on defense and detection, offensive security thinks like an attacker finding weaknesses before bad actors do. It helps organizations understand their real security risks, improve their defenses, and strengthen incident response.
Key Reasons to Adopt Offensive Security
Stay Ahead of Attackers: Identify and mitigate vulnerabilities before they can be exploited.
Example: A government financial regulator conducted penetration tests on their cloud-based transaction monitoring system. This uncovered misconfigured access controls, allowing them to prevent unauthorized access to sensitive financial records.
Test Real-World Defenses: Ensure that security controls and protocols are functioning effectively.
Example: A national critical infrastructure organization performed a red team exercise to simulate a state-sponsored cyberattack. The exercise revealed delays in incident detection, prompting an upgrade to their Security Information and Event Management (SIEM) system.
Comply with Regulations: Meet industry-specific compliance requirements, such as GDPR or PCI DSS.
Example: A retail bank carried out quarterly penetration testing on their payment processing platform to ensure compliance with both regional and international financial regulations.
Safeguard Critical Assets: Protect sensitive data, financial information, and operational systems from compromise.
Example: An insurance company simulated insider threat scenarios to ensure privileged access management was configured correctly, protecting policyholder data.
Adopting offensive security not only improves resilience but also enables organizations to make informed decisions about their cybersecurity investments.
Defining the Right Objectives for Your Offensive Security Engagement
One of the biggest mistakes companies make when planning an offensive security engagement is not having a clear objective. Many go into security testing just to “check the box” for compliance or because they feel it’s something they should do. but without a solid plan, the engagement won’t provide real value.
Steps to Define Your Offensive Security Objectives
1. Identify What You Want to Learn
Are we trying to find technical vulnerabilities in our applications?
Do we want to assess how well our security team detects attacks?
Are we testing for real-world business risks, such as fraud or insider threats?
2. Prioritize Based on Business Risk
Critical Business Systems: Payment processing platforms, customer data storage, financial reporting systems.
Public-Facing Applications: Web portals, APIs, and mobile apps that interact with customers.
Third-Party Integrations: Cloud services, vendor APIs, or external tools that connect to your environment.
3. Define the Scope Clearly
Which systems, networks, and applications will be tested?
Should testing include third-party vendors or cloud services?
Are there any restrictions (e.g., testing must be non-disruptive to operations)?
Methodology/Framework | purpose | when to use |
---|---|---|
MITRE ATT&CK | Simulates real-world adversary tactics and techniques. | When testing detection and response capabilities against known attack patterns. |
OWASP Testing Guide | Focuses on identifying vulnerabilities in web applications and APIs. | Best for application security assessments. |
NIST Cybersecurity Framework (CSF) | Provides a structured approach to risk management and security program development. | When aligning security assessments with organizational risk management efforts. |
PTES (Penetration Testing Execution Standard) | A structured approach to penetration testing, covering pre-engagement interactions, threat modeling, and exploitation. | When conducting detailed penetration tests across networks, applications, and infrastructure. |
The frameworks listed above are some of the most widely used in offensive security engagements, but they are not the only ones. Depending on the industry, regulatory requirements, and specific security goals, organizations may also consider other methodologies
Determining the Right Type of Offensive Security Engagement
Different types of offensive security engagements serve different purposes. Choosing the right one depends on your objectives, security maturity, and the threats you need to test against.
Objective | recommended engagement |
---|---|
Identify vulnerabilities in applications (web, mobile, APIs) | Application Penetration Testing |
Assess weaknesses in IT infrastructure (internal & external networks, cloud, IoT) | Network Penetration Testing |
Test how well security teams detect and respond to real-world attacks | Red Teaming |
Collaborate between offensive (red team) and defensive (blue team) teams to improve detection & response | Purple Teaming |
Simulate attacks from specific threat actors to validate defenses | Adversary Emulation |
Identify misconfigurations, outdated software, and security gaps | Vulnerability Assessments |
Understanding Methodologies and Frameworks
Choosing the right methodology ensures that security assessments align with industry best practices and real-world attack scenarios. Different frameworks serve different purposes, and selecting the right one depends on your organization’s objectives.
Example: A healthcare provider used the NIST CSF to guide its offensive security engagements, ensuring that penetration testing efforts aligned with broader risk management and compliance requirements.
Choosing the Right Service Provider
The success of offensive security testing depends heavily on the approach and flexibility of the service provider. Organizations should prioritize providers that go beyond certifications and standard checklists, focusing instead on real-world scenarios and customized testing strategies.
What to Look for in a Service Provider
- Scenario-Based Testing: Providers should design tests that simulate realistic attack scenarios specific to the organization’s threat profile. This ensures the testing mimics how adversaries would target the organization’s assets.
- Customizable Services: The provider should adapt their methodologies to align with the unique requirements and goals of the organization, instead of relying on rigid frameworks.
- Comprehensive Methodologies: Instead of focusing on compliance checklists, the provider should emphasize identifying business logic flaws, critical vulnerabilities, and real-world attack vectors.
- Collaboration and Insight Sharing: A good provider should work closely with the organization’s internal teams to ensure knowledge transfer, helping the organization improve its overall security posture.
Questions to Ask Providers
How do you design scenarios that reflect our specific threat landscape?
Can your testing approach be customized to align with our business-critical systems and unique goals?
Do you focus on business logic and complex attack scenarios beyond standard compliance checks?
How will you collaborate with our internal teams to enhance our long-term security capabilities?
Choosing the right offensive security service provider is critical to ensuring a valuable and effective engagement. Not all providers approach security testing the same way, and selecting one that aligns with your objectives can make the difference between a meaningful assessment and a generic checklist-driven test.
Measuring Success
Measuring the effectiveness of offensive security is essential to demonstrate its value.
Key Metrics
How Many Identified Issues Were Actually Fixed?
Did the Engagement Help Improve Detection & Response?
Did the Engagement Uncover Business Logic or Process Gaps?
How Did the Engagement Improve Long-Term Security Strategy?
A successful offensive security engagement isn’t just a test—it’s a learning experience that helps an organization become more secure, more resilient, and better prepared for real-world threats.
By focusing on these success criteria, organizations can ensure that offensive security engagements provide real security value—far beyond a compliance checkbox.
Conclusion
Offensive security, when done right, is not just about finding vulnerabilities—it’s about enhancing an organization’s security resilience, improving detection and response capabilities, and ensuring security efforts align with real-world threats. By defining clear objectives, selecting the right engagement type, and measuring success based on actionable outcomes, companies can move beyond compliance and build a truly effective cybersecurity strategy.
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