In a world where cloud security threats are outpacing endpoint risks six to one, a staggering 80% of SMB tenants we scan exhibit significant Microsoft 365 misconfigurations. This alarming statistic highlights a critical area for MSPs to focus on—not just defending the endpoint but actively managing and optimizing cloud-based licenses that are often underutilized or completely overlooked.it’s no surprise that Microsoft 365 misconfigurations are among the top concerns for MSPs managing small business clients.

But here’s the kicker: while many MSPs are focused on defending the endpoint, the real opportunity—for both protection and profit—sits in the cloud. And more specifically, in the Microsoft licenses your clients already use... or don’t.

In a recent video, I break down how MSPs are turning licensing misalignment into real revenue—without needing to upsell unnecessarily or rely on technical jargon that clients won’t understand. (Watch it here)

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Licensing Isn’t Just About Cost—It’s About Capability

Most SMBs don’t know what’s included in their Microsoft 365 subscription. Whether they’re on Business Basic or E5, the reality is that many aren’t using the features that matter—or worse, don’t have access to the controls that protect them.

From a security perspective, that’s risky. From a business perspective, that’s an opportunity.

At Overe, we built Overe Assess (our free service) to make those conversations easier. It’s a lightweight tool that gives MSPs a clear snapshot of a client’s M365 posture: where they're protected, where they’re exposed, and—critically—what licensing they actually need to close those gaps.

Real Problems = Real Projects

What we consistently find is that around 80% of SMB tenants we scan are misconfigured in some material way. And there’s typically a licensing misalignment that’s limiting what security controls are even possible.

For an MSP, that data translates directly into work = revenue:

• Helping a client move from Business Basic to Business Premium to unlock Intune or Defender for Business.
• Building recurring value through quarterly posture reviews that show measurable improvements.
• Upselling to other services like, Overe Protect to offer fully automated security for M365

And yes, this can drive license resale uplift of Microsoft services, with typical margins around 15-20%. But as noted in the video—it’s the projects and services layered around the license where the real margin lives.

‍Enhance Margins with Strategic Upgrades

For example, leveraging Overe Assess allows you to guide your clients from Microsoft Business Standard ($12.50/user/month) to Business Premium ($22.00/user/month) effectively:

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It’s Not About Pushing E5 on Everyone

Let’s be clear: this isn’t a pitch to move every SMB client to E5. That’s not realistic, and most don’t need it. Instead, it’s about making tailored, context-aware recommendations backed by posture data. When you can show exactly what a client is missing—and how the right license helps address it—you turn a technical conversation into a business decision.

Lead with Insight, Not Assumptions

You don’t need to guess which clients are under-protected. Just scan. Overe Assess is free to use, with unlimited clients and unlimited scans. Whether it’s onboarding a new prospect or prepping for a QBR, the goal is to lead with data and show clients the “why” behind your recommendations.

If you’re an MSP already reselling Microsoft 365, there’s a clear path to increase your revenue per client while improving their security baseline. And if you're not reselling yet—this might be the right moment to reconsider.