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Navigating the CMMC Compliance Maze: Lessons from the Front Lines

Eligibility for many Department of Defense contracts will hinge on passing a Cybersecurity Maturity Model Certification (CMMC) Level 2 assessment. For organizations handling Controlled Unclassified Information (CUI), CMMC is a revenue gate. 

But when defense contractors first hear about CMMC, the reaction is often the same: “We’ll buy the right licenses and we’re good, right?” That can be a dangerous assumption. 

In our webinar, Navigating the Path to CMMC Compliance: A Buyer’s Guide, Rich Baron, SVP of Operations at CyberSheath, shared what actually happens when organizations approach CMMC the wrong way and what separates first-time passes from expensive remediations. 

Rich’s experience guiding multiple organizations through successful Level 2 assessments aligned with NIST SP 800-171 reveals a consistent pattern: Compliance isn’t something you buy. It’s something you operate. 

The Myth of Partial Compliance 

Partial compliance is noncompliance, and you want to pass your audit the first time. 

Achieving CMMC Level 2 with a perfect score requires implementation of all 110 security controls in NIST SP 800-171. There is no 80% solution. 

Think of compliance like building a bridge. If you complete 80% of it, you don’t have a bridge, you have a liability. 

Failing an assessment can mean: 

  • Delayed contract awards
  • Ineligibility for new DOD work
  • Expensive remediation cycles
  • Paying for a second assessment 

Passing the first time isn’t a preference. It’s a business requirement. 

Why Only Buying Licenses Won’t Save You 

One of the most common missteps Rich sees? Organizations rushing to purchase Microsoft GCC High because someone told them it was required. 

Months later, they still not CMMC compliant. 

Licensing isn’t going to monitor your network or write your system security plan. It’s just one piece of the puzzle. 

A license will not: 

  • Write your System Security Plan (SSP)
  • Develop and track POA&Ms
  • Execute documented patch management
  • Conduct incident response exercises
  • Produce audit-ready artifacts 

Technology enables compliance. It does not create it. 

True CMMC readiness requires alignment across people, process, and technology. Miss one, and the entire system collapses under audit scrutiny. 

Auditors don’t score what you purchased. They evaluate how you operate. 

Vendor Red Flags That Lead to Overspending, Under-Complying, and Audit Failure 

There are recurring, all-too-common warning signs organizations should watch for when selecting a compliance partner that can introduce serious operational and financial risk: 

  • License-First Pitches: If a provider begins with “just buy GCC High and you’re compliant,” scoping hasn’t been done.
  • Partial-Solution Claims: There is no “80% of Level 2” under CMMC.
  • Fake Badging: Claims like “DFARS certified” — those certifications do not exist.
  • FedRAMP as the Whole Story: FedRAMP and FIPS matter where CUI is stored, processed, or transmitted. But they do not replace implementing all 110 applicable controls across your actual environment — especially in hybrid or on-prem environments common in manufacturing and OT networks.
  • Hype Without Proof: “Trusted by thousands” isn’t evidence. Ask for successful assessment references in organizations similar to yours in industry, size, and complexity. 

To help buyers navigate these pitfalls, we compiled a detailed checklist of vendor red flags and must-ask questions in The CMMC 2.0 Compliance Buyer’s Guide. 

The Contract Risks No One Talks About 

Beyond technical implementation, contractual blind spots often create the greatest exposure. 

“Security never sleeps,” noted Rich. “There is no second chance in security.” If your vendor charges additional fees to respond to a breach, you are exposed at the worst possible moment. 

Financial Risk 

  • Extra charges for incident response
  • Hidden emergency remediation fees
  • Unexpected audit support costs 

Operational Risk 

  • 24/7 monitoring not included
  • No clear ownership of compliance documentation
  • Weak control-mapping accountability 

Contractual Risk 

  • Vendor-owned tenancy or licensing
  • Lock-in clauses
  • One-sided termination penalties 

“Can you imagine having an incident response document that says if I pay, then things keep going?” Rich asked. If incident response isn’t built into your agreement, you don’t have a true security partner. 

Compliance Never Stops. Make It a Daily Operational Outcome. 

Passing your C3PAO assessment is a milestone, but it’s not the finish line. As Rich explained during the webinar: 

“The biggest misconception is that compliance stops after certification. Even the day after you pass your C3PAO assessment, it’s great—but that doesn’t mean we wait three years until the next cycle. There are many different things that can take place inside of that time.” 

Why? Because your business evolves: 

  • New hires change access control requirements
  • Infrastructure modifications impact scope
  • Systems move in or out of the enclave
  • Threat actors adapt 

Compliance must be treated as an ongoing operational capability, supported by: 

  • Continuous monitoring
  • Vulnerability and patch SLAs
  • Annual internal assessments
  • Tabletop exercises
  • Documented change management
  • Executive governance oversight 

For example, as Rich explained: “Your change management procedure isn’t just about having a tool, it’s about having a process and the right people involved.” 

You might purchase a change tracking platform. But if you lack a documented change review process, security stakeholder involvement, evidence of approvals, and audit trails of implemented changes, then you’ll fail that control. 

Build controls to harmonize people, process, and technology—auditors want to see how you run, not just that a tool exists. Compliance should become a natural byproduct of daily operations, not a once-every-three-years scramble. 

A Practical Roadmap to CMMC Level 2: The Four-Phase Lifecycle for Sustainable Compliance 

Organizations that successfully achieve CMMC Level 2 certification tend to follow a disciplined four-phase approach:

1. Kickoff: Scope CUI, define system boundaries, align stakeholders, and establish governance ownership.

2. Build: Conduct gap assessments, develop the SSP, construct POA&Ms, deploy controls, and document policies.

3. Go Live: Operationalize monitoring, validate evidence collection, and prepare for assessment readiness.

4. Ongoing Management: Maintain continuous monitoring, conduct internal reviews, update documentation with system changes, and reinforce executive oversight.

When executed correctly, compliance becomes embedded into business operations, not layered on top of them. 

Questions Every Buyer Should Ask 

Don’t just ask what tool a vendor is selling. Ask how they’re getting you across the finish line. Before signing with any compliance partner, question: 

  • Does your solution achieve full CMMC Level 2 compliance? What’s excluded?
  • Which specific NIST 800-171 controls do you implement directly? Show the control mapping.
  • How many organizations have you guided through successful Level 2 assessments?
  • Who owns the licensing and tenancy?
  • Is incident response included contractually in the base agreement?
  • What happens if we fail our assessment? 

If those answers aren’t clear, the risk is yours. 

What the Right Compliance Partner Actually Looks Like 

Not all CMMC partners are built the same. As organizations move toward CMMC 2.0 readiness, one reality becomes clear: the right partner doesn’t sell point solutions. They take a compliance-first approach and support your business at every stage of its journey, even as requirements evolve. 

Here’s what that looks like in practice.

1. They Solve the Whole Compliance Challenge

CMMC isn’t just an IT project. It spans regulatory interpretation, technical control implementation, security operations, documentation, governance, and audit evidence. 

The right partner integrates: 

  • Regulatory alignment (including NIST SP 800-171 control mapping)
  • IT architecture design (cloud, enclave, hybrid, on-prem)
  • Security operations and monitoring
  • Policy, documentation, and audit preparation 

Fragmented vendors create fragmented compliance. Integrated support closes gaps before auditors find them. 

2. They’re Flexible Enough to Match Your Maturity 

Some organizations are just beginning their CMMC journey. Others already have mature security programs and need refinement, validation, and operationalization.

A strong partner adapts to both. Whether you’re: 

  • Defining CUI scope for the first time
  • Standing up a compliant enclave
  • Scaling controls across multiple business units
  • Preparing for your first C3PAO assessment 

The approach should flex to your reality, not force you into a rigid, one-size-fits-all model.

3. You Retain Control of Your Environment and Data

Compliance should never mean surrendering ownership. The right partner ensures: 

  • You own your licenses and tenancy
  • You maintain full control over your data
  • Documentation and artifacts remain accessible
  • Exit terms are clear and fair 

If your compliance environment is controlled by your vendor, you don’t have a sustainable solution, you have dependency risk.

4. Breach Response Is Built In — Not an Add-On

Security incidents don’t pause because of contract fine print. A true compliance partner includes: 

  • Rapid incident response
  • Expert-led breach remediation
  • Root cause analysis
  • Documentation updates to restore compliance posture 

Restoring operational security and restoring compliance are not separate activities. They must happen together.

5. Operational and Emergency Support Are Always Available

CMMC isn’t a one-time event, it’s an operating model. That means you need support for: 

  • Day-to-day monitoring and ticketing
  • Change management reviews
  • Evidence collection
  • Internal assessments
  • Audit preparation
  • Rapid response during incidents or external assessments 

Compliance maturity depends on consistency and consistency requires accessible expertise.

6. Deep, Evolving Expertise

CMMC 2.0 requirements continue to mature. Guidance clarifies, threat actors adapt, and scope changes. Your partner should include specialists across: 

  • Regulatory compliance
  • IT architecture
  • Security operations
  • Governance and risk management 

And they should proactively stay ahead of changes so you’re not reacting at the last minute. 

The Strategic Reality 

Achieving full CMMC 2.0 compliance consumes significant internal resources: executive time, IT bandwidth, operational focus, and financial investment. 

Selecting the wrong partner doesn’t just slow progress. It makes compliance harder, more expensive, and riskier. The right partner solves the whole problem in a way that works for your business model, technical environment, and growth plans. 

Anything less creates gaps that surface at the worst possible time: during an audit, a breach, or a contract award decision. 

The Bottom Line and Next Steps 

CMMC compliance is not a procurement exercise. It is an operational transformation. There are no shortcuts or partial compliance when it comes to CMMC. And there is little margin for error when DOD contract eligibility is at stake. 

Organizations that treat compliance as a strategic capability—not a licensing decision—are the ones that pass on the first attempt and sustain eligibility long term. 

If CMMC Level 2 is on your roadmap this year, start by evaluating whether your approach is tool-driven or operationally mature. Download the CMMC Compliance Buyer’s Guide as a framework for making that decision. 

That distinction determines whether you pass—or pay twice.