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Microsoft officially ends support for Windows 10 in October 2025. That might feel like plenty of time; why worry now when there are so many other things you need to worry about? But for equipment dealerships, especially those managing complex IT setups, it’s crucial to start planning now.

Whether you’re overseeing a fleet of computers in your dealership or just trying to keep the day-to-day operations running smoothly, this change is more than just an IT issue—it’s a business continuity challenge.

Why should you care now?

Windows 10 has been a solid operating system for years, but with Microsoft ending its updates and support, the risks of sticking with it become significant. Without regular security patches and bug fixes, your business’s systems could be vulnerable to cyberattacks and data breaches. Any cyberattack or breach can disrupt your operations, damage your reputation, and even lead to hefty financial losses.

History can be a great indicator of the future, and when Microsoft ended support for Windows 7 in 2020, many businesses delayed upgrades, exposing themselves to cyberattacks. After the end of Windows 7 support, the FBI had to warn companies that hackers were actively targeting businesses that were still using the outdated OS. Similar risks will emerge when Windows 10 support ends in 2025, meaning any machine not upgraded could become an easy target for attackers.

But here’s the thing: upgrading your systems isn’t just about security. It’s about budgeting and planning ahead to avoid last-minute panic, rushed decisions, and higher costs.

Budgeting and planning for the upgrade

IT planning can feel like a nuisance for many business owners and executives. We get it—why deal with software upgrades when you’ve got dealerships to run? But the reality is that leaving these upgrades to the last minute can be much more expensive and stressful than preparing ahead.

When businesses waited to upgrade from Windows 7, they were forced to pay up to £150 per device annually for extended security updates (ESUs), which were only available for a limited time. Businesses that failed to plan ahead often had to make rushed upgrades, paying higher costs to replace incompatible hardware. It was a costly challenge at the time.

Imagine discovering a year from now that half your machines are running on unsupported Windows 10 systems, scrambling to upgrade at premium prices, or worse—being hit with a cyberattack that could’ve been prevented with a simple update.

Start by evaluating your current systems:

· How many machines are running Windows 10?

· What will it cost to upgrade them to Windows 11 (or beyond)?

· What other software or hardware will need upgrading to be compatible?

This audit will give you a clear view of what’s needed and allow you to create a budget spread over the coming year, minimizing disruptions and financial shocks.

Love it when someone else manages IT

Here’s where we come in. We understand that most machine dealerships aren’t in the business of loving IT—that’s our job. But the beauty of outsourcing your IT to a managed services provider like us is that we take care of these transitions for you, ensuring your business stays secure and your systems run smoothly.

Let us handle the technical details, from assessing your current setup to upgrading and securing your machines. Our team loves IT, and we know that, in time, you’ll love it too—especially when you don’t have to deal with the stress and complexity yourself.

Final thoughts

You have a business to run, and IT is just one piece of the puzzle. However, ignoring changes like the end of Windows 10 support can put your entire operation at risk. By planning ahead, you can avoid last-minute chaos, budget efficiently, and stay ahead of any security threats that could come your way.

Reach out to us today to start planning your upgrade path. We’ll handle the IT, so you can focus on what matters—running your dealership

Written by

Kevin possesses the unique ability to understand, and explain in non-threatening and non-technical ways how technology, business and team members work with, and sometimes, against each other. He has an innate ability to understand how technology works at the basic conceptual level and how it interacts with hardware, software, networking, people and business processes. A rare combination in today's technology arena.

Kevin lives in Charleston, South Carolina with his bride Summer, their two sons - Caleb and Isaiah - and their Vizsla wonder dog Dexter.