Risk Management

When the Bots Start Doing Billy’s Job (Part 4)

Written by:  William White, CISSP

Chief Technology Officer, Ultimate Risk Services

(Part 4 in our AI vs AI series)

Don’t Let AI Create Your CMMC Policies 

Why Letting AI Write Your CMMC Cybersecurity Policies Is a Risky Shortcut

There’s a growing temptation in cybersecurity circles: “Why not just have AI write our policies?”

After all, AI is fast, fluent, and can generate documents that look like they were written by a committee of very serious people who use phrases like “robust control framework” without irony.

For many use cases, that’s fine.

But if you’re aiming for CMMC compliance, letting AI take the wheel on your cybersecurity policies is less “efficiency hack” and more “creative way to fail an assessment.”

Let’s talk about why you should leave your CMMC policies to the professionals. 

1. CMMC Is Not a Template Exercise

CMMC (Cybersecurity Maturity Model Certification) isn’t just a checklist you casually breeze through with a well-formatted document. It’s a structured framework with very specific practices and processes that must be implemented and demonstrable.

AI tends to approach policy writing like this:

“Here is a very professional, generally applicable policy that sounds correct.”

CMMC assessors approach it like this:

“Show me exactly how your organization satisfies this specific requirement.”

That gap between generic correctness and specific applicability is where AI-generated policies tend to fall apart. 

2. “Mostly Covered” Is the Same as “Not Covered”

AI is very good at getting things mostly right.

Unfortunately, CMMC is very good at penalizing “mostly.”

Each control has nuances:

  • Specific documentation expectations

  • Defined roles and responsibilities

  • Evidence of implementation

  • Alignment with your actual environment

AI might:

  • Combine multiple requirements into one vague statement

  • Miss subtle distinctions between similar controls

  • Omit edge-case requirements that still count

And in an assessment, missing even part of a requirement isn’t partial credit—it’s a finding. 

3. Your Environment Is Weird (And AI Doesn’t Fully Know How)

Every organization believes they aren’t unique with their general IT needs. Most aren’t wrong… arguably.

However, when it comes to cybersecurity environments, everyone is weird in their own very specific, very compliance-relevant ways.

You might have:

  • A hybrid cloud/on-prem setup with legacy systems

  • Contract-specific data handling requirements

  • Third-party dependencies that complicate control ownership

  • Operational workarounds that never made it into official diagrams

AI doesn’t see any of that unless you explicitly and exhaustively tell it; and, even then, it may not interpret those nuances correctly.

So it writes policies for an idealized version of your organization.
CMMC evaluates the real one. 

4. CMMC Requires Traceability, Not Just Readability

A good CMMC policy isn’t just readable… it’s traceable.

You need to be able to map:

  • Each policy statement → to a specific CMMC control

  • Each control → to implementation evidence

  • Each implementation → to actual system behavior

AI-generated policies often lack this precision. They sound comprehensive, but they aren’t structured for:

  • Control-by-control validation

  • Audit defensibility

  • Clear evidence mapping

In other words, they look good right up until someone asks, “Where exactly do you address AC.L2-3.1.1?” and the answer is… “somewhere in paragraph four, probably.” 

5. AI Doesn’t Understand the Auditor’s Mindset

CMMC compliance isn’t just about meeting requirements; it’s about proving you meet them.

That means thinking like an assessor:

  • What questions will they ask?

  • Where will they look for gaps?

  • What counts as sufficient evidence vs. hand-waving?

AI doesn’t have audit anxiety. It doesn’t anticipate scrutiny. It doesn’t write with the quiet paranoia that comes from knowing someone will try to poke holes in every sentence.

Humans who’ve been through audits do.

And that experience shows up in how policies are written… Tight, explicit, and defensible. 

6. The Hidden Risk: False Confidence

This might be the most dangerous part.

AI-generated policies often look so polished that they create a false sense of security:

  • “This seems comprehensive.”

  • “We’ve covered everything.”

  • “We should be good for the assessment.”

But compliance failures rarely come from obviously bad policies.
They come from subtle gaps that weren’t caught early.

AI doesn’t raise its hand and say:

“I might have missed a requirement that will cost you certification.”

It just keeps writing confidently. 

7. Where AI Can Help (Without Getting You in Trouble)

To be fair, AI isn’t the villain here, it’s just being over-trusted.

Used correctly, it’s actually quite helpful:

  • Drafting initial policy language

  • Translating technical controls into plain English

  • Suggesting structure aligned to frameworks

  • Highlighting potential gaps (as a second opinion, not the final one)

But the key word is assist.

Final policy ownership, especially for CMMC, needs to stay with someone who:

  • Understands the framework deeply

  • Knows your environment intimately

  • Can defend every line in front of an assessor 

Final Thought

If you let AI write your CMMC cybersecurity policies, you’ll likely end up with something that looks impressive, reads smoothly, and passes a quick glance test.

What you may not get is something that actually passes a CMMC assessment. And in the world of compliance, that distinction is everything. Because when the assessor walks in, they’re not grading your writing style.

They’re verifying your reality.

And that’s one test you don’t want AI taking on your behalf. Let the pros handle that for you.

 

When the Bots Start Doing Billy’s Job (Part 3)

Written by:  William White, CISSP

Chief Technology Officer, Ultimate Risk Services

(Part 3 in our AI vs AI series)

In a previous post (about getting your CISSP to keep your job), I stated:

“Try asking an AI to convince a senior executive to invest in a security initiative that won’t show ROI until after something bad happens. Exactly.”

But then I got to thinking again…hmmm…

Who would be more effective at convincing, a CISSP or a machine? This is within the per view of a CISO , after all.

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In 2026, the cybersecurity landscape has undergone a tectonic shift. According to the World Economic Forum’s 2026 Global Cybersecurity Outlook, over 94% of security leaders now identify AI as the primary driver of cyber risk. Hackers are no longer just using scripts; they are deploying "Agentic AI"—autonomous bots that can scout, adapt, and attack with superhuman speed.

To help you navigate this, we’ve synthesized the latest 2026 guidance from the CISA (Cybersecurity and Infrastructure Security Agency), FBI, and NIST into an actionable defense plan.

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In the world of government contracting and infrastructure, "security" used to mean high fences and badges. Today, the perimeter has shifted. Whether you are a small sub-contractor or a mid-sized engineering firm, your most vulnerable asset isn’t your job site—it’s your data.

At URS (Ultimate Risk Services), we see compliance not just as a regulatory hurdle, but as a competitive advantage. When you "level your defenses," you aren’t just satisfying an auditor; you’re telling your partners and the Department of Defense that you are a reliable link in the chain.

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Most business leaders know cybersecurity matters. You’ve invested in antivirus software, firewalls, and backups. You may even have policies in place.

So why do breaches still happen?

Because the most dangerous cyber risks aren’t always dramatic or obvious. They’re quiet. Routine. Easy to overlook. And that’s exactly why hackers love them.

Cybercriminals rarely “break in” the way movies portray. Instead, they walk through doors that were accidentally left open—doors created by small gaps in everyday operations. These hidden weaknesses are called cybersecurity blind spots, and nearly every organization has them.

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Now that you have established a strategy for Cybersecurity Supply Chain Risk Management (C-SCRM), the next logical step is to identify exactly who is in your "supply chain ecosystem". As the recent NIST SP 1305 guide points with, you cannot treat every vendor the same way. A cloud provider holding your company’s intellectual property requires much stricter oversight than a vendor providing office furniture.

This process is known as Activity 2: Identifying and Prioritizing Suppliers.

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In today’s world, no piece of technology is an island. Whether you are using a laptop, a smartphone, or a cloud service, that product was built using an extensive, global network of parts, software, and people. This network is known as the Supply Chain Ecosystem.

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Think about the last time technology got in the way of your work instead of supporting it. Maybe email went down during a busy day, a system update broke something critical, or a “quick fix” turned into hours of lost productivity. For many small and mid-sized businesses, IT has quietly become a major source of stress.

That’s why IT outsourcing has moved from being a “nice to have” to a serious consideration. Instead of managing everything internally, companies are partnering with outside experts to handle their technology more efficiently and securely. But does that approach actually make sense for your business? Let’s take a fresh look.

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The Cybersecurity Maturity Model Certification (CMMC) Level 2 is a critical step for Department of Defense (DoD) contractors who handle Controlled Unclassified Information (CUI). Unlike Level 1, which covers basic safeguarding of Federal Contract Information (FCI), Level 2 builds a comprehensive cybersecurity program, aligning with NIST SP 800-171 Rev 2.

Level 2 is the foundation for advanced security practices and is often required for prime contractors and subcontractors managing sensitive DoD information. Compliance ensures that your organization is protected against cyber threats while maintaining eligibility for defense contracts.

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Every October, Cybersecurity Awareness Month reminds us that digital safety isn’t just a tech issue — it’s a people issue.
In reality, most cyber incidents don’t start with a sophisticated hacker breaching firewalls. They begin with something small and human: a missed software update, a reused password, or a hasty click on a fake link.

The truth is, your organization’s strongest defense isn’t the latest security tool — it’s consistent, smart habits practiced every single day.

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Your business is thriving. Sales are strong, your team is productive, and your systems seem to be running like a well-oiled machine.

Then — out of nowhere — everything freezes. Emails stop. Customer orders vanish. Phones are silent. You've just been hit by a cyberattack.But no worries, right? You’ve got cyber insurance. The policy’s paid, the paperwork is in order, and you've been reassured time and again that you're covered. Or so you thought.

How Forgotten Office Devices Like Old Printers Can Open the Door to Hackers

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🎯 The Forgotten Devices That Could Be Your Biggest Cybersecurity Threat

You walk past it every day.
A printer stuffed in a closet.
An old router blinking away under a pile of cables.
A dusty PC under a desk, never turned off, never updated.

They seem harmless, right?

But in the cybersecurity world, those forgotten, outdated devices are like wide-open windows in an otherwise locked-down building.

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Cyberattacks are no longer a rare occurrence—they’re a daily threat to individuals and organizations alike. Unfortunately, many people don't realize they've been compromised until significant damage has occurred. Understanding how to recognize the warning signs of a breach and knowing how to respond can help you prevent further harm, preserve your data, and recover with minimal disruption.

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The Hidden IT Risk That Could Cripple Your Business During a Cyberattack

When executives plan for cybersecurity threats, they usually focus on external risks—malware, phishing, ransomware, and bad actors breaching the network. But one of the most dangerous threats is already inside the organization: undocumented, unwritten IT knowledge—also known as tribal knowledge.

💰 Why Cutting Your Cybersecurity /IT Security Budget Could Cost You More Than You Think

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In today’s fast-paced economy, small and medium-sized businesses (SMBs) are constantly looking for ways to save money. Trimming the budget might seem smart — until it puts your entire business at risk. One of the most common but dangerous areas businesses cut? Information and cyber security.

❌ Cost-Cutting Mistake: Slashing Cybersecurity

Many SMBs believe that cybercriminals only target big corporations. That’s a dangerous myth.

🔐 60% of small businesses that suffer a cyberattack go out of business within six months, according to the U.S. National Cyber Security Alliance.

Cybersecurity isn’t a luxury. It’s business survival.

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Launching a new business is tough. Keeping it running during a crisis? Even tougher. Whether you're facing a cyberattack, a flood, or a major supply chain disruption, the difference between shutting down and staying strong often comes down to one thing: technology.

This isn’t just about having the right tools. It’s about using them strategically to ensure your business stays resilient, responsive, and ready for anything. That’s the power of tech-driven business continuity planning

Why a Disaster Recovery Plan (DRP) Is Critical for Every Business

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What Happens Without a Plan?

Businesses without a DRP face serious consequences:

  • 43% of businesses fail after a catastrophic data loss without a recovery plan

  • 93% go bankrupt within a year if they can’t restore data within ten days

  • Small outages cost thousands: small firms lose around $8,000/hour, mid‑size $74,000, and large enterprises $700,000/hour in downtime .

  • Many businesses lack plans: 1 in 5 SMB executives say they don’t have a recovery strategy

  • Even when backups exist, 58% fail during actual recovery due to outdated tech or inadequate testing

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What would happen to your business if your systems went down tomorrow?

Think of all the things that could bring your business to a halt: a power outage, a flood, a cyberattack, a key employee leaving suddenly. Without a plan, even a small disruption can snowball into major financial loss, lost customers, and damage to your reputation. That’s where Business Continuity Planning (BCP) comes in.

What Is Business Continuity and Why Should You Care?

Business Continuity is simply about making sure your business keeps running—even during a crisis. It involves having a written, tested plan that outlines how your operations, people, systems, and data will recover from disruptions.

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1. What Is SharePoint — and Who’s Affected?

SharePoint is a document‑sharing platform that many organizations run on their own servers, not the cloud. These are called on‑premises SharePoint servers, and they’re widely used in schools, hospitals, government agencies, and businesses