Windows 10 End of Life: Upgrade Paths for Enterprises

Windows 10 end-of-life enterprise - Corsica Technologies
Windows 10 end-of-life enterprise - Corsica Technologies

It’s that time again. A Windows operating system is becoming EOL (end of life). From small businesses to enterprises, everyone is looking for the right upgrade path from Windows 10 to Windows 11. Whether you’re on your own or working with a managed IT services provider, it’s time to determine how you’ll keep your computers secure while supporting your team’s technology needs.

Luckily, it isn’t the eleventh hour. You have time to make an informed decision that fits your organization.

Here’s everything you need to know about Windows 10 becoming EOL.

How long will Windows 10 be supported?

Microsoft will stop providing full support for Windows 10 on October 14, 2025. At that time, these specific types of service and updates will no longer be available:  

  • Technical support
  • Feature updates
  • Security updates and patches

Machines running Windows 10 will still work, but as time goes on, their risk of security breaches will increase, since Microsoft will no longer provide security updates.

If you need more time before you upgrade, you can enroll your workstations in Microsoft’s one-year Extended Security Updates program, which costs $30 per device. This program provides only critical and important security updates. It doesn’t provide other updates or technical support.

What is the adoption rate for Windows 11?

According to Statcounter, Windows 11 had 43.23% of the Windows desktop market as of May 2025, the last full month reported.

That’s up from 27.67% one year ago. However, Windows 10 still held 53.2% of market share in May 2025.

Windows 11 adoption is certainly picking up, having grown 56% in the space of 12 months. But the market has a way to go in realizing the full potential of Windows 11.

If you haven’t upgraded to Windows 11 yet, you’re in good company—but it’s time to start thinking about the future.

Windows 11 - Why upgrade? - Corsica Technologies

Is it worth upgrading to Windows 11?

Yes, it’s absolutely worth upgrading to Windows 11. The security benefits alone are enough to make the change worthwhile for large and small enterprises. You don’t want your workstations to become sitting ducks for cyberattacks.

Of course, there are other benefits beyond cybersecurity. Windows 11 comes with new features and capabilities that will make your team more productive.

Here’s what you get in Windows 11 that wasn’t available in Windows 10.

  • A new GUI that makes it easier than ever to navigate your computer.
  • Smart recommendations in file searches and the Start menu.
  • Your computer can automatically wake as you approach it and lock when you leave.
  • Built-in capabilities for voice transcription to text.
  • Voice commands for opening apps, minimizing windows, scrolling, and more.
  • File restoration in addition to file backup.

These are only a few highlights. Get the full picture from Microsoft here: Windows 11 vs. Windows 10.

Will upgrading to Windows 11 delete my files?

The short answer is no, as long as your upgrade is installed correctly and you select the option to retain files and applications.

Of course, as with any operating system upgrade, it’s best to back up all your files beforehand. This ensures that you don’t lose anything in case the upgrade isn’t implemented correctly.

When you work with a service provider like Corsica Technologies, you can rest assured that every workstation is properly backed up, your files are safe, and every upgrade is performed correctly.

Windows 11 workstation compatibility - Corsica Technologies

What if our workstations don’t support Windows 11?

Older machines may not be compatible with Windows 11. You can use Microsoft’s PC Health Check application to determine if a workstation is compatible, or your IT service provider can advise you.

If your computers aren’t compatible, you’ll need to upgrade to machines that can run Windows 11. There are two ways to accomplish this.

Which option is right for your organization?

The answer depends on two factors:

  1. Whether you have the cash reserves on hand to purchase new computers.
  2. Whether you prefer capex (capital expenditure) or opex (operating expenditure) for meeting your hardware needs over the long term.

Generally speaking, organizations with limited cash reserves but stable cashflow get a better value out of HaaS.

How can enterprises seamlessly upgrade to Windows 11?

The answer depends on many factors.

  • How many computers are on Windows 10 Enterprise?
  • How many are compatible with Windows 11?
  • Are you purchasing Windows 11 Enterprise?
  • Do you want to move to a HaaS model as part of your Windows 11 upgrade?
  • Do your users have essential software on their machines that will need to be upgraded as well?
  • Does your organization have cloud storage in place (OneDrive or SharePoint), or is everyone saving files locally?
  • Do you want to roll out Microsoft Copilot as part of your Windows 11 upgrade?
  • When should you perform the upgrade based on seasonal activity and demand?

Each of these factors will help determine what a good upgrade plan looks like. You can go through this process yourself, developing this plan, or you can engage a trusted partner. Here at Corsica Technologies, we’ve helped numerous companies transition seamlessly to Windows 11. No two upgrades are the same, and we help organizations determine their goals and the right processes to achieve them.

The takeaway: Plan now for your Windows 11 upgrade

The Windows 10 EOL date is just under five months away. There’s time to make plans—but not that much time. It’s good to start now so you have everything in place to execute before October 14th. Here at Corsica Technologies, our Microsoft experts can work with you to understand your current status with Windows computers, where you want to end up, and how you’ll get there. Contact us today to start your Windows upgrade process.

Ready to upgrade to Windows 11?

Reach out to schedule a consultation with our Windows specialists.

Garrett Wiesenberg
With over a decade of experience in IT, Garrett Wiesenberg brings deep technical expertise and a strong commitment to strategic problem-solving. For the past four years, he has focused on architecting and delivering advanced solutions for managed clients, consistently aligning technology with business outcomes. Garrett’s career has spanned a variety of roles—from service desk technician to senior network engineer—and now, as Vice President of Solution Consulting, he leads with a hands-on, business-focused approach. He holds several industry-recognized certifications, including CCNA Route & Switch, CCNA Security, CCNA Wireless, MCSA: Server 2012 R2, MCSA: O365 Administration, NSE 1–3, and CMNA.

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