If you’re still running Windows 10 on your office computers, you’re definitely not alone. A recent survey found that 82% of businesses have yet to make the leap to Windows 11, even though most devices are ready for the upgrade.
With the end of Windows 10 support on the horizon—October 14, 2025, to be exact—it’s time to start thinking seriously about making the switch.
But if upgrading feels overwhelming, don’t worry. Let’s break down the reasons why you should consider upgrading now, the common hurdles businesses face, and some simple solutions to get ahead of the curve.
What’s the Hold-Up? Why So Many Businesses Haven’t Upgraded Yet
Despite Microsoft offering a free upgrade to Windows 11, many businesses are understandably hesitant. Some key concerns are:
Compatibility Issues: If you’ve been in business long enough, you’ve probably dealt with the headache of older software not working with a new system. For many SMBs, this fear is real. Legacy or custom-built business applications might need tweaking or even a full overhaul to work smoothly on Windows 11.
Memories of the Windows 10 Upgrade: Remember how tricky that was? Businesses that struggled with the transition from Windows 7 to Windows 10 are understandably wary about doing it again. Compatibility problems, downtime, and unexpected costs all contributed to those migration headaches.
The Cost of New Hardware: While 88% of devices running Windows 10 are ready for Windows 11, a small percentage (about 11%) will need to be replaced entirely because they don’t meet the system requirements, like needing a Trusted Platform Module (TPM) 2.0 chip. For some businesses, that’s a significant investment.
Why Upgrading to Windows 11 Makes Sense
Let’s shift the focus to why upgrading is worth it, especially when weighed against sticking with Windows 10 until the very last minute.
Security Comes First: We all know that cyberattacks are on the rise, and once Microsoft ends support for Windows 10, you’re left wide open to security vulnerabilities. Windows 11 has built-in features like hardware-enforced security that make it far more resistant to attacks. If you want to keep your business data—and your customers’—safe, this alone is reason enough to upgrade.
Future-Proofing Your Business: Windows 11 is designed to work smoothly with modern hardware, meaning your newer devices will run more efficiently. Plus, Microsoft is gearing up Windows 11 to support AI-based tools. Whether or not you’re ready to adopt AI now, upgrading will prepare your business for this inevitable shift.
Avoiding the Extended Security Costs: If you don’t upgrade by the deadline, you’ll be paying Microsoft for extended security updates. And these updates aren’t cheap. The first year will set you back $61 per device, and it only gets more expensive from there. By the third year, you’re looking at $244 per device. Why wait and pay extra?
Tackling the Common Hurdles
So what’s stopping your business from upgrading? Let’s look at some of the most common roadblocks—and how to overcome them.
Worried About Compatibility? Test Before You Leap
It’s true that some legacy apps might not work perfectly on Windows 11, but you don’t have to guess. Tools like ControlUp’s Windows 11 readiness assessment can help you figure out which of your apps and devices are good to go and which might need updates or replacements.
Concerned About Downtime? Go for a Phased Approach
Upgrading doesn’t have to be an all-at-once affair. You can implement a phased rollout, upgrading a few machines at a time to minimize disruption. That way, if any issues pop up, they won’t bring your entire business to a standstill.
Facing Budget Constraints? Start Small and Plan Ahead
If upgrading all your systems feels like a financial stretch, start with the critical devices first, especially those that are most exposed to security risks. By spreading the upgrades over time, you can budget more effectively without compromising your business’s security.
Take Action Now (Before It’s Too Late)
Upgrading to Windows 11 might feel like one more thing to add to your ever-growing to-do list, but it’s not something you want to put off until the last minute. The risk of security vulnerabilities, escalating costs for extended updates, and potential operational disruptions all make it crucial to start planning your upgrade now.
Here’s what you can do today:
- Assess Your Devices: Use tools to check if your devices are ready for Windows 11.
- Prioritize Security: Upgrade the most exposed systems first to reduce your cybersecurity risks.
- Create a Timeline: Don’t wait until October 2025 to start upgrading. A phased approach will make the transition easier and more affordable.
With some planning and the right tools, upgrading to Windows 11 can be a smooth process that keeps your business secure and future-ready.