Why Delaying Windows 10 Upgrades is a Risky Business 

Quick Summary 

• You already know Windows 10 support ends October 2025. 
• So why have so many not upgraded yet? 
• IT teams are battling legacy apps, hardware constraints, business risk aversion, and budget cycles. 
• We break down the real blockers, and how Trustco can help you speed through the process with our expertise. 

We All Know the Date. So, What’s the Hold-Up? 

Let’s skip the basics: if you’re an IT professional, you don’t need reminding that Windows 10 hits end-of-support on 14 October 2025. You know the risks. You’ve flagged them. You’ve probably raised it at least three times in board meetings. 

But here we are – and a huge number of organisations haven’t made the leap to Windows 11 yet. According to a Forbes report from April, around 900 million devices were still on Windows 10. So, what’s getting in the way? 

The Real-World Challenges of Migrating to Windows 11 

Upgrading isn’t just a technical task – it’s a business-wide shift that can throw up all sorts of complications. We’ve been on the ground with IT teams dealing with exactly this, and here’s what we’re seeing: 

Legacy App Compatibility 

Some business-critical applications just won’t play nicely with Windows 11. It’s not just about replacing them. It’s about revalidating workflows, managing vendor upgrades, or isolating legacy environments safely. 

Hardware Doesn’t Make the Cut 

Windows 11’s hardware requirements (hello, TPM 2.0) mean many devices, even some bought in the last few years, are out. That leaves IT teams juggling refresh budgets, leasing options, and supportability trade-offs. 

Business Risk Aversion 

For many, “If it ain’t broke…” is still alive and well.  

Exec teams want guarantees and to avoid disruption. IT gets stuck in analysis paralysis trying to de-risk the whole thing instead of being empowered to phase in change properly. 

Budget Timing and Priorities 

It’s one of a dozen competing IT priorities. Even when you have the plan ready, the funding isn’t. Or worse: it gets bumped for a shinier, more ‘strategic’ project. That ‘strategy’ could be a very costly mistake. 

What’s at Stake If You Wait Too Long 

Just because everyone knows the date doesn’t mean you can jump ship the day before, there will be teething problems. In fact, the longer the delay, the more painful and expensive the transition becomes. Here’s just a few highlights that we see a lot of: 

• Security blind spots: Unpatched vulnerabilities become open doors. 
• Insurance compliance gaps: Unsupported systems can void policies. 
• Rising support costs: Legacy systems require more firefighting. 
• Lost productivity: Crashes, compatibility issues, frustrated users and endless support tickets. 

The delay can simply add urgency and anxiety to your IT teams. No one likes to hear the ticking clock. 

How Trustco Can Help 

We don’t make fancy guarantees, like ‘migration in 7 days’, because we understand the complexities of organisational setups means that is unfeasible and a promise waiting to be broken. We use our knowledge of past Windows 11 migrations to improve our service on an on-going basis 

Tailored Windows 11 Migration Services 

Whether you need full hardware refresh, in-place upgrades, or a phased hybrid rollout, we can scope, plan, and deliver a migration path that fits your setup – not a copy and paste job from our last customer’s experience. 

Bonus: We handle the comms, change management, and user training too. Less drama. Less disruption. 

Extended Security Update (ESU) Planning 

Need more time? We’ll help you license, track, and budget for Microsoft’s ESU programme – including year-on-year cost modelling, so it’s a stopgap, not a trap. 

Virtual Desktop Isolation for Legacy Apps 

Still got a Win10-only app that runs some critical function? We’ll help you isolate it securely via virtual desktop infrastructure (VDI), local or cloud – so it doesn’t hold your estate back. 

Strategic Refresh Planning 

Device refresh doesn’t have to be a blunt instrument. We’ll help prioritise based on real usage, compatibility, and lifecycle. So, you’re not overspending or under-resourcing. 

Fewer Deadlines. More Decisions 

Windows 10 going EOL isn’t the surprise. What matters now is what you do next – and how to do it without taking your business down in the process. 

If you’re stuck in the “we’ll get to it” phase, or struggling to get internal buy-in, let’s talk. We’ll help you cut through the blockers, make a plan that works in the real world, and get moving. Contact Trustco today about your Windows 11 migration plans.