Act Now: Why That 24-Hour Upgrade Window from Microsoft Matters for Your Business

If your business is still running Windows 10, you’re now facing a critical decision point. Microsoft ended support for Windows 10 October 14, 2025. After that date, Windows 10 devices no longer received security updates, feature updates, or technical support—leaving them at elevated risk.

But here’s the twist: Microsoft is offering an extension via the “Extended Security Updates” (ESU) program—effectively giving you extra time to secure your systems. The catch? You need to act, and fast. If you delay, you can inadvertently open your business to security threats, compliance gaps, and downtime. Let’s break down what this means for small and mid-sized businesses (SMBs) and outline the actionable steps you should take right now.

Why This Matters for SMBs

1. Security & cyber-risk: Once Microsoft stops delivering patches, any newly discovered vulnerabilities in Windows 10 will go unaddressed. That means hackers and threat actors may increasingly target outdated systems—because they know the “patch gap” is open. As an MSP with over 20 years’ experience helping SMBs, I can confirm that unsupported OSes are high-risk assets.

2. Productivity & support overhead: Older systems aren’t just riskier—they’re more costly. Unsupported machines may fail, run slowly, have software compatibility issues, and shift the support burden back on your internal team or MSP partner (that’s me). Avoiding the upgrade now often ends up costing more later.

3. Compliance & insurance impact: If you handle customer data, regulated info, or sensitive business operations, running unsupported software can complicate compliance (e.g., insurance underwriting, audits). From a liability standpoint, this is not the time to gamble.

4. Window to transition: The ESU program offers a bridge—not a permanent fix. Use this period to plan a clean upgrade path to Windows 11 or to modernize your hardware and platform strategy. That’s critical in today’s economic environment where stretching IT dollars matters.

What the Offer Actually Gives You

Here are the key components of the extension:

• Eligible devices must be running Windows 10 version 22H2.

• The ESU program allows continued receipt of critical and important security updates for up to one additional year, through October 13, 2026.

• Enrollment options: either pay (a fee per device), redeem Microsoft Rewards points, or—in certain markets—enroll for free by syncing your PC’s settings via OneDrive/Windows Backup.

• After the deadline, unsupported systems will keep working, but with significantly elevated risk and no “safety net.”

What You Should Do (Now)

Here’s a step-by-step plan tailored for SMBs:

Step 1: Inventory your devices: Immediately identify all PCs running Windows 10 in your organization. Document the version (must be 22H2 or higher), hardware age, and whether they’re upgrade-eligible for Windows 11.

Step 2: Review eligibility for Windows 11: Use Microsoft’s PC Health Check or the built-in “Check for updates” path to determine whether each machine qualifies to upgrade to Windows 11. (If not, you’ll need to plan either a hardware refresh or continue via the ESU bridge.)

Step 3: Enroll in the ESU program if staying on Windows 10: If your devices cannot yet transition, enroll them in the ESU extension before the cut-off date. Ensure devices are on version 22H2, fully patched, signed into a Microsoft Account if required, and that you choose the free or paid pathway depending on your region.

Step 4: Build your upgrade roadmap: Don’t treat this as optional. Plan a phased upgrade—hardware refreshes, OS upgrades, testing, user training. Use the extension year to give yourself breathing room, not to procrastinate indefinitely.

Step 5: Communicate internally: Inform your staff or clients (if you manage systems externally) that the OS is changing. Set expectations around timelines, possible hardware refreshes, and any interruptions.

Why Waiting Is Not a Strategy

Putting this off introduces several dangers:

• Zero-day vulnerabilities on unsupported OSes become “low-hanging fruit” for attackers.

• Compliance flags can appear during audits when running unsupported systems.

• Longer upgrade runway means hardware will be older, risk of failure increases, support becomes harder.

• Budget squeeze: In an economically tight year, delaying means the cost of reactive fixes may outweigh planned upgrades.

Final Thoughts for Southeastern Wisconsin SMBs

If your business is in the Milwaukee/Racine/Kenosha area and you’re still on Windows 10, this moment demands action. Whether you’re running manufacturing, nonprofit, professional services, or a veteran-owned business, the risk-reward calculus is clear: you can extend your Windows 10 OS for another year—but only if you take that step now and treat it as a bridge. Your true target should be a modern, supported environment that reduces operational risk and IT spend.

If you’d like help assessing your device fleet, mapping upgrade paths, estimating cost-benefit, or developing a communications plan to your users, I’m happy to assist.

Call to Action: Don’t wait until the last minute. Schedule a OS-audit within the next 24 hours. Make sure you’re eligible, choose your path (upgrade vs. ESU), and get your plan in motion.