Security Testing: You’re Playing By The Rules, They’re Rewriting The Game

Sauron had a ring to rule them all, but unfortunately, no tool was forged in the fires of Mount Doom to single-handedly secure modern software.

When discussing application security, the DAST vs. SAST debate inevitably comes up. It’s an old argument, one that too often falls into a narrow, binary mindset. Static vs. dynamic, code vs. runtime, white-box vs. black-box. If that’s your frame of reference, you’re already on the wrong path. Security isn’t a contest between methodologies. It’s about layering defenses and thinking beyond the toolset.

Static or Dynamic Application Security Testing?

Static Application Security Testing (SAST), or white-box testing, makes perfect sense on paper. You analyze source code, identify vulnerabilities before they reach production, and developers get to fix security issues early. It’s efficient, cost-effective, and a key part of the shift-left philosophy. But here’s the problem: SAST lacks real-world context. Just because something appears vulnerable in code doesn’t mean it’s exploitable in practice. Testing generates a lot of noise and endless false positives that frustrate developers, overwhelm security teams, and ultimately could allow real threats to slip through the cracks.

Dynamic Application Security Testing (DAST), or black-box testing, on the other hand, shifts the focus to execution. It assesses how an application behaves under attack conditions in a live environment. Misconfigurations, broken authentication, and runtime flaws, issues which SAST might miss, become glaringly obvious with DAST. The trade-off? DAST can only test what it sees. If a vulnerability is hidden deep within logic that isn’t triggered during testing, it remains undetected.

This is where the debate typically unravels. People get caught up in choosing a side, arguing over which method is “better.” Some might even argue the benefits of gray-box testing. The in-between solution of providing the testers with some level of insight, such as credentials. Regardless of which method, what's the reality? Neither is sufficient alone. Relying purely on SAST is like reviewing a building blueprint while ignoring the construction process. Depending solely on DAST is like stress-testing the final structure but never inspecting the foundation. You need both perspectives to get a complete picture. They're needed in different contexts and stages of the security lifecycle.

The right approach is a strategic blend. Use SAST early to eliminate obvious flaws before deployment. Leverage DAST later to identify real-world risks. But here’s the kicker: automation alone will never be enough. No scanner, no matter how advanced, can truly think like an attacker. The best security programs don’t just rely on tools; they leverage human ingenuity, offensive expertise, and continuous adaptation. Exploiting an application is rarely a one-step process. Remote code execution is not typically achieved through a single attack vector. In most cases several vulnerabilities are chained together in order to exploit the application.

Scenario Time: Chaining Attacks

To understand chaining, consider this scenario: A web application is vulnerable to path traversal, allowing an attacker to read arbitrary files on the server hosting the application. This could lead to sensitive data exposure, where confidential information, never meant for public access, falls into the wrong hands. Among the exposed files, the attacker discovers a stored API key in an old email stored as a file. With this key, they gain unauthorized access to restricted areas of the application, bypassing authentication controls. With elevated access, the attacker stumbles upon a file upload feature, potentially within an administrative console. The feature lacks input sanitization, permitting the upload of a malicious avatar image embedded with a reverse shell. Once the script is executed, perhaps when an uploaded avatar is loaded by an admin, the attacker establishes remote command execution on the underlying server. What started as a simple file read vulnerability has now escalated into full system compromise through attack chaining.

SAST would have detected the insecure file handling that enables path traversal, flagging it as a potential risk but lacking the context to determine what sensitive files could be accessed. DAST, testing against the running application, would have confirmed that directory traversal is possible, identifying that files outside the intended directory structure could be retrieved. However, neither automated approach would have recognized the significance of an exposed email file containing an API key. Manual testing plays a critical role in interpreting the leaked data, understanding its value, and leveraging it for further exploitation. Once authenticated using the stolen API key, SAST might have flagged the lack of input validation on the file upload feature, while DAST could have confirmed the ability to upload arbitrary files. Still, it would take human reasoning to chain these findings together, recognize that an uploaded file can be accessed and executed, and ultimately achieve remote code execution on the server.

Choosing The Right Methodology

Security isn’t about checklists, nor is it about picking the “right” methodology. It’s about execution, strategy, and staying ahead of adversaries who aren’t bound by rules or tool limitations. It’s how you gain real visibility into risk. If you’re serious about security, stop searching for silver bullets. Start thinking like an attacker. It's not about blindly following industry trends but about understanding context. It’s about knowing when to use SAST to empower developers and when to deploy DAST to assess real-world attack surfaces. Security is an evolving discipline. One that requires continuous refinement, adaptability, and a mindset shift. Organizations that truly embrace security don’t just scan and patch; they learn, iterate, and integrate security into every aspect of development.

Enter, Microsoft’s Security Development Lifecycle (SDL), which embeds security requirements at every phase of software development. By integrating security from the start, teams can reduce vulnerabilities before they ever reach production, minimizing costs and risks. But SDL isn’t just about scanning code, it prioritizes proactive threat modeling. Identifying potential attack vectors early allows teams to architect security into the core of an application rather than treating it as an afterthought.

Threat modeling isn’t just another security exercise; it’s a way to outthink adversaries before they strike. Instead of treating security as a patchwork process, teams should approach it like a chess game by anticipating threats, questioning assumptions, and continuously evolving their models. The most secure organizations aren’t the ones with the most tools. They’re the ones who see security as a competitive advantage and stay ahead of the attacker’s next move.

What About DevOps 8?

But wait a minute. This sounds like DevOps 8. Is this the silver bullet you just said doesn't exist? Not quite. DevOps 8 builds on the foundation that SDL laid, but it’s not a replacement, it’s an evolution. Where SDL focused on integrating security into traditional development lifecycles, DevOps 8 acknowledges that modern software development doesn’t move in neat, sequential steps. It’s fast, continuous, and highly automated. Security can’t afford to be a gatekeeper. It has to be embedded, automated, and adaptable. The key difference? DevOps 8 treats security as a living, breathing part of the pipeline, shifting left while staying responsive to threats in real time. It’s not about running a SAST scan and calling it a day. It’s about security that moves at the speed of DevOps, integrating threat modeling, continuous validation, and real-world attack simulation into the entire workflow. The companies that truly get this aren’t just deploying secure software, they’re building security resilience into the very DNA of their development culture.

Don’t Gamble With Your Security Posture

It's not an afterthought; it’s foundational. It’s one of the first things that should be embedded into the development lifecycle because it delivers immediate, tangible results. Without testing, you’re making security decisions in the dark, hoping the development process got it right. That’s not strategy, that’s gambling. Security testing validates whether your measures actually hold up under scrutiny. It’s the difference between assuming a workload is secure and knowing where the cracks are.

By incorporating a holistic and layered testing strategy, you can reduce the risk of security blind spots. The key is to integrate multiple layers of security validation and continuously refine testing processes. A truly resilient security posture is built on proactive testing, strategic layering of tools and methods, and a mindset that anticipates threats before they manifest. It's a combination of automatic testing as well as manual penetration testing. Attackers don’t stick to one technique, why should defenders?

Read more about Security Testing and Threat Modeling practices in Microsoft's Service Development Lifecycle, or read about the DevOps Application Lifecycle.

Are you interested in hearing more about Security Testing, Threat Modeling, or DevOps? Let us know!

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