Windows 10 End of Life Is Coming: What It Means for Your Business

Windows 10 support officially ends on 14 October 2025—a date that’s creeping up faster than many IT departments might realise. But what does this actually mean for organisations still using Microsoft’s most widely adopted operating system? 

As our consultants Matt and Chris discussed in our recent podcast, the implications go far beyond simply running “unsupported software.” From security vulnerabilities to application compatibility, the ripple effects will impact your entire business tech strategy. 

So, if you have devices running Windows 10, what should you do? Upgrade to 11 now? Wait for Windows 12? Ignore it all and hope for the best? We’ll go through your options below. 

Fancy watching rather than reading? Check out the full video podcast below, or read on for our take on what Windows 10 “end of life” really means for your business. 

When we talk about “end of life” for Windows 10, it doesn’t mean the OS will suddenly stop working. 

In Microsoft’s own words, “technical assistance and software updates will no longer be provided”. 

This means there are several practical implications that’ll directly affect your business: 

• No more security updates or patches: This is perhaps the most critical aspect—your machines won’t receive protection against new vulnerabilities and threats. 

• End of Microsoft support: If something goes wrong, you can’t ring Microsoft for help. You’re on your own. 

• Third-party vendor support issues: Application vendors will gradually stop supporting Windows 10, creating a domino effect where even if your OS technically works, your business apps might not be supported. 

• No new features: While Windows 10 hasn’t seen major feature updates for some time, you’ll miss out on cool new toys like Microsoft Copilot and other AI integrations in Windows 11. 

As Chris noted in our discussion, “You could take a chance, and stuff might work, but if you run into a problem and your vendor says it’s not supported on this platform—it leaves you in a difficult position.” 

Microsoft will offer extended support for organisations that can’t migrate immediately, through their Extended Security Update Program. It comes at a price, though. The cost is reported to double each year: 

• Year 1: $61 per device per year 

• Year 2: $122 per device per year 

• Year 3: $244 per device per year 

• Year 4: $488 per device per year 

And you have to pay a year in one go—there aren’t any monthly or quarterly billing options. Clearly, it’ll get pretty expensive if you leave it too long. (For individuals or Windows 10 Home customers, the ESU program will cost $30 for one year.) 

There are some exceptions worth noting. If you’re using Azure Virtual Desktop (AVD) or Windows 365 Cloud PC, extended support is included at no additional cost. However, we still recommend planning for migration rather than relying on this indefinite extension. 

We believe extended support makes sense for very specific scenarios—perhaps you have mission-critical custom software that only runs on Windows 10 and represents a significant investment. In that case it’d be sensible to extend your time with it. Manufacturing environments with specialised equipment control systems often fall into this category, for example. 

For most businesses, however, investing in a proper migration strategy is going to be a more cost-effective path than paying ongoing extended support fees. 

If you absolutely must keep certain Windows 10 machines running beyond the support deadline, security should be your primary concern. 

We recommend several approaches: 

• Network segregation: Place legacy systems on isolated network segments with strict access controls. 

• Air-gapping: For truly critical systems, consider removing internet connectivity entirely. 

• Zero trust approach: If internet access is necessary, implement stringent controls to limit access to only essential services. 

• Physical security: Don’t forget about protecting the physical machines themselves.

Chris highlighted that with proper diligence, unsupported systems can be protected: “If you’re aware of these vulnerabilities and mitigate against them by removing your machines from the internet, you’ve removed a very big attack vector.” 

That said, we have to emphasise that no mitigation strategy is foolproof. Each introduces operational complexity and still carries risk. Consider these measures as temporary solutions while working towards a proper upgrade path. 

For companies using Azure Virtual Desktop with Windows 10 multi-session, the upgrade path requires careful planning. Microsoft’s official stance is that in-place upgrades from Windows 10 to Windows 11 for AVD are unsupported. 

There are several reasons for this: 

• Image cleanliness: AVD images often accumulate configuration artefacts and legacy settings over time. 

• Profile management: FSLogix profile containers may require reconfiguration. 

• Application compatibility: Applications need thorough testing in the new environment. 

While some IT administrators might be tempted to try an unsupported in-place upgrade (and indeed, you can find unofficial guides online), we strongly advise against this approach. As Matt points out, “We’ve seen comments from people who’ve attempted this, reporting problems with applications hanging, logon issues, and FSLogix crashing.” 

When you’re supporting hundreds of users, these kinds of issues create massive operational headaches. 

Instead of going rogue with a DIY upgrade, we recommend: 

1. Creating a fresh Windows 11 image 
2. Thoroughly testing all applications 
3. Implementing new group policies specific to Windows 11 
4. Establishing new profile containers 
5. Migrating users in controlled batches 

Yes, this approach requires more initial effort, but it provides a clean, stable foundation for your virtual desktop environment going forward. During the transition, you’ll likely need to maintain both environments temporarily, which means some additional costs—but these are offset by the benefits of a properly executed migration. In the long run, it should be worth it. 

The most time-consuming aspect of any OS migration is often application compatibility and redeployment. We’ve seen several approaches to managing this challenge: 

• Intune deployment: Using Microsoft Intune to deploy applications to your Windows 11 environment can streamline the process, particularly for modern applications. 

• MSIX packages: These newer application packaging formats promise easier deployment, though we’ve found they work best with simpler applications. 

• App-V virtualisation: Separating applications from the OS layer can simplify migration, though it requires initial setup effort. 

• Third-party tools: Solutions like PDQ Deploy can help automate application installation across your environment. 

“The dream,” as Matt puts it, “is having a base image with all your applications managed through Intune. Then, as new builds come out, you can quickly deploy them without spending hours reinstalling apps and recreating complex configurations.” 

In reality, most organisations will need a hybrid approach. You’ll likely have at least one legacy application that needs special handling—and these are often the most business-critical ones. 

Our strongest recommendation: document everything. Every application, every configuration setting, every group policy. This will not only make your Windows 11 migration smoother but will also pay dividends for future upgrades. 

With rumours circulating about Windows 12 potentially arriving in late 2025 or early 2026, some organisations might be tempted to skip Windows 11 entirely. We understand the logic, but we don’t recommend this approach. 

Several factors influence our thinking: 

1. Timing: Windows 10 support ends in October 2025. Even if Windows 12 releases shortly after, you’d be operating unsupported systems in the interim. 
2. First release stability: As Chris notes, “I’d probably never push out the first release of an operating system to something like AVD until it’s properly tested”. Wait until it’s more stable. 
3. Migration complexity: Each migration gets more complex the longer you wait, as you accumulate more customisations and dependencies. 
4. Potential delays: We’ve seen it before with Microsoft—release dates can slip. As Chris mentioned in the podcast, the October 2025 date might get pushed back again, and the same could happen with Windows 12. Betting your strategy on rumoured release dates is risky business. 
5. Hardware requirements: Windows 12 is rumoured to have significantly more demanding hardware requirements due to its AI features. Your current hardware upgrade plan for Windows 11 might not cut it for Windows 12, potentially requiring another round of investment. Things could get pricey. 

It’s worth remembering that the Windows 10 end-of-life date itself was already pushed back six months from April to October 2025. As Chris pointed out, “Microsoft almost seemed to want to cover up the fact that they had to push it back.” Planning your business around speculative release dates is dangerous territory. 

Rather than playing the waiting game, we suggest moving forward with Windows 11 migration planning now. This gives you plenty of time to test, refine your approach, and handle any unexpected complications. 

Based on our experience supporting clients through multiple OS transitions, here’s what we recommend: 

1. Start planning now: Don’t wait until late 2025 when resources will be stretched thin. 
2. Conduct application inventory: Identify potential compatibility issues early. 
3. Test thoroughly: Especially for AVD environments, test with a small user group before broader deployment. 
4. Budget appropriately: Account for potential hardware upgrades, temporary dual environments, and staff time. 
5. Engage stakeholders: Ensure business leaders understand the necessity of the change, while users are prepared to deal with it. 

OS migrations have an impact beyond just your infrastructure—they affect how your users work every day. Taking the time to properly plan and execute the transition will minimise disruption and maximise the benefits of moving to a modern, supported operating system. 

Synextra is here to help if you have questions about your Windows 10 to Windows 11 migration. Our friendly team of Azure specialists has extensive experience with transitions like these, particularly in complex environments.  

Get in touch to discuss your situation and we’ll see how we can help make your upgrade journey smoother.