A Pentest Wednesday™ Story
Every security leader knows about Patch Tuesday. It’s the rhythm Microsoft set decades ago to deliver updates and fixes, and it quickly became a mainstay of IT and security operations. Teams plan change-windows around it. Vendors align updates to it. And for many organizations, Patch Tuesday has become the de facto symbol of “staying secure.”
But here’s the uncomfortable truth: patching is only half the battle. Applying a patch doesn’t guarantee that the underlying risk is eliminated. Misconfigurations persist. Legacy systems don’t behave the way you expect. And attackers don’t care whether a vendor says a vulnerability is “fixed” — they care whether it’s exploitable in your environment.
That’s why I believe for every Patch Tuesday, there should be a Pentest Wednesday.
To see why Pentest Wednesday matters, look at how one of the nation’s largest healthcare systems put the concept into practice.
The Customer
One of the nation’s largest healthcare systems, operating hundreds of hospitals and clinics across the U.S., faced a challenge shared by many in the sector: securing a vast IT estate while ensuring that patient-care devices and clinical systems remained safe and operational. In healthcare, even the smallest disruption carries risks beyond IT — it can impact patient safety.
The Problem
A Big 4 consultancy audit made it clear their current approach to vulnerability management wasn’t enough. The recommendation: adopt a Continuous Threat Exposure Management (CTEM) strategy. The timing was urgent. The security team was already swamped in scanner output, so noisy and unmanageable they estimated it would take five additional full-time staff just to keep pace.
Scanner data wasn’t telling the full story, and point-in-time pentests offered little proof of actual business risk. Compliance-driven efforts pushed the team to chase low-value issues while critical exposures went unvalidated.
AHA Moment
When the healthcare system deployed NodeZero®, the difference was immediate. Within weeks, the platform safely executed more than 60 adversarial tests, mapped dozens of network segments, and uncovered exploitable attack paths their scanners had completely missed.
Unlike other tools that require heavy setup or constant tuning, NodeZero’s streamlined configuration and ease of deployment allowed the team to scale quickly without adding overhead — a critical factor for large enterprises with complex environments and limited staff capacity.
One security leader summarized the shift:
Scanner data wasn’t telling the full story. We needed to move from theoretical vulnerability management to exploitability and exposure management.
The Outcome
NodeZero quickly became the foundation of their CTEM program, enabling them to accelerate remediation with closed-loop workflows in Jira and ServiceNow. Results included:
- 60+ tests executed in the first weeks, creating a new rhythm of continuous validation.
- 30+ network segments mapped for ongoing coverage across the enterprise.
- A unified risk view that aligned IT, security, and executive leadership.
- Compliance-ready evidence to support HIPAA, PCI, and cyber insurance audits.
- Faster integration and divestiture validation during M&A activities, giving teams a “clean bill of health” across new environments.
For the first time, the board and executives could see which risks truly mattered.
Importantly, all of this was achieved without disrupting sensitive clinical systems. Tests were designed to minimize operational impact while delivering actionable proof. In healthcare, where uptime is a matter of patient safety, that balance proved decisive.
Why Pentest Wednesday Matters
Patch Tuesday is a useful milestone, but it represents only one side of the equation. It’s about vendor-driven updates. Pentest Wednesday is about organization-driven validation.
On Patch Tuesday, software companies tell you what to fix. On Pentest Wednesday, you confirm whether those fixes actually matter in the context of your environment.
- Patch Tuesday is about assumptions. Pentest Wednesday is about evidence.
- Patch Tuesday is about vendor priorities. Pentest Wednesday is about your business priorities.
- Patch Tuesday is about applying fixes. Pentest Wednesday is about proving impact.
When you make Pentest Wednesday part of your security rhythm, you gain confidence that your defenses hold up in practice — not just on paper.
The Future of Security is Verification
This healthcare provider’s story is just one example of a shift that’s long overdue in our industry. For too long, security has been built on faith in tools, reports, and compliance checklists. Pentest Wednesday flips that model. It says: don’t just trust — verify.
The organizations that adopt this mindset find themselves better prepared, more resilient, and more confident. They know not just what they patched, but what they proved.
In an era where threats move fast, where attackers exploit chains of weaknesses in hours or even minutes, the difference between theory and proof can mean the difference between resilience and compromise.
So here’s my challenge: when you sit down after Patch Tuesday, ask yourself — what will you validate on Pentest Wednesday?
Each week, I’ll be sharing new stories from the field — real-world examples of how organizations are using Pentest Wednesday to turn assumptions into evidence, and uncertainty into confidence.