The True Cost of Delaying Your Windows 11 Migration

Procrastination nearly always comes at a cost.

Delay taking out your garbage? Stinky.

Delay bedtime because you’re too busy scrolling? Crabby.

Delay upgrading your Windows 11 migration because you’re too busy or want to wait until it’s closer to the drop-dead date? Inconvenient at best, and likely expensive.

Before we reimagine the personalities of all seven of Snow White’s companions, let’s get to the point. (We do not want to see a remake with Stinky, Crabby, Inconvenient, and Expensive.)

Windows 10 will stop receiving support on October 14, 2025. If that date is on your calendar, it better be for trick-or-treating or a costume party—not because you still need to execute the migration. Migration should be a distant memory by that point, and that means you need to start now.

Save Now, Pay More Later

At first glance, putting off the transition to Windows 11 might seem like a cost-saving move. After all, upgrading hardware, testing applications, and executing a rollout all come with associated expenses—especially if you’re not careful about the platform you use. But when you look at the full picture, it becomes clear that the costs of delay can quickly outweigh any short-term savings.

That’s not just talk. Let’s look at the true cost: First, there’s the issue of extended support. Once Windows 10 reaches end-of-life in October 2025, Microsoft will start charging steep fees to continue supporting the OS. In the first year, it’s $61 per user. In the second year, that doubles to $122. By the third year, you’re looking at a staggering $244 per user. For large organizations, these costs can quickly add up to millions of dollars—a significant drain on IT budgets.

Who Will Get The Competitive Advantage?

The financial impact goes beyond support fees. Delaying migration also means missing out on any performance enhancements, security features, and management capabilities that Windows 11 may offer. Even if you can theoretically do without the speed and functionality, it’s worth noting that Windows 10 will stop receiving security support after October 2025. That alone should be a reason to upgrade, on top of avoiding productivity issues and increased operational costs over time.

There’s also the matter of competitive advantage to consider. As more and more organizations move to Windows 11, those still on Windows 10 risk falling behind in digital capabilities and agility. You already know how fast the business world is evolving, particularly with the rise of artificial intelligence and machine learning. You should be grabbing any thoughtfully considered advantage you can.

Fortunately, these costs and risks are avoidable. By starting the migration process now, you can spread expenses over time, avoid last-minute rushes, and ensure a smooth, well-executed transition. Solutions like ControlUp can further streamline the process, providing real-time visibility into hardware and application readiness, automating critical migration tasks, and minimizing end-user disruption.

Psst: need help? We already have our sleeves rolled up and are ready to dive in. From assessing compatibility pre-migration to streamlining deployment with a human-centric migration to optimizing post-migration performance, our solutions are designed to deliver tangible, measurable results that maximize results and mitigate costs. 

Learn how you can access your Windows 11 readiness with just one click!