Windows 10 Enterprise End of Life: What Your Organization Should Be Doing

Is your business ready for Windows 10’s end of life?

Many businesses are staring down a fast-approaching IT deadline — Windows 10 Enterprise end of life is coming October 14, 2025. While that may sound far off, upgrading an entire fleet of devices, coordinating app compatibility and ensuring cybersecurity compliance will take more than a few months to execute well. If you’re still running Windows 10 Enterprise, it’s time to move from planning to action.

We should note, that as of March 2025, Windows 10 remains the most widely used desktop operating system, accounting for approximately 54.2% of the market share worldwide.

This article will help IT leaders, system administrators and CIOs prepare for the end of Windows 10 support. We’ll break down what end of life really means, the risks of delaying your migration and the concrete steps organizations should take today to avoid downtime, data breaches and operational disruption. We’ll also touch on the long-range view, including the Windows 11 end of life date and why you should factor that into long-term planning.

Let’s start with the basics — what does “end of life” mean for your business?

What End of Life Means for Windows 10 Enterprise

Microsoft’s end-of-life policies are clear: once a product reaches its end of support, it no longer receives security updates, patches or technical support. For Windows 10 Enterprise, that date is October 14, 2025, and it applies to the latest supported version of Windows 10 22H2, which is also the final feature update for Windows 10.

Here’s what that means in practice:

• No more monthly security updates, including critical vulnerability fixes.
• No technical support from Microsoft for issues on Windows 10.
• No new driver updates, application compatibility updates, or bug fixes.
• Increased risk of software or hardware incompatibility with future tools and services.

Even organizations running enterprise-grade Microsoft support contracts will see support taper off. Businesses that don’t upgrade will either pay for extended security updates (if eligible) or face serious security gaps.

Key Risks of Inaction

Waiting too long to address Windows 10 end of life introduces several risks to your organization.

For example, unsupported systems become high-value targets. Without regular security patches, any new vulnerabilities discovered after EOL remain unpatched, leaving you open to ransomware, phishing and zero-day exploits.

One of the most urgent and dangerous consequences of Windows 10 Enterprise reaching end of life is the loss of security updates, which directly increases your organization’s exposure to cyberattacks. According to a report by the Ponemon Institute, 60% of data breaches in 2023 link to unpatched software vulnerabilities.

When Microsoft stops delivering monthly security patches on October 14, 2025, any vulnerabilities discovered after that date will go unaddressed on systems still running Windows 10. That gives threat actors a clear and growing attack surface.

Unsupported operating systems are frequent targets of cybercriminals who rely on known, unpatched exploits. Attackers often reverse-engineer security updates released for supported versions to identify vulnerabilities they can exploit on legacy systems still in use.

Ransomware thrives in these conditions. Without patching, endpoints become easy entry points for malware delivery. In high-compliance sectors — such as healthcare, finance and defense — this risk could also translate to violations of regulations like HIPAA, PCI-DSS or CMMC.

You have to worry about more than external threats. Internal risks — such as misconfigured systems, outdated antivirus software and unmonitored network access — are harder to detect on unsupported platforms. Logging, auditing and integration with security information and event management (SIEM) tools may become unreliable as compatibility fades.

Delaying the upgrade to Windows 11 or newer supported platforms isn’t just a compliance issue; it’s a direct threat to your security posture. Cyber insurance providers and security auditors increasingly flag unsupported operating systems as red flags that can raise premiums or disqualify coverage entirely.

Organizations should prioritize migrating their most critical endpoints and user groups to mitigate these risks. Consider layering additional defenses, such as endpoint detection and response (EDR), during the transition period — but make no mistake: Running Windows 10 past its end-of-life date introduces unacceptable long-term risk.

What Your Organization Should Be Doing Right Now

Preparing for the Windows 10 Enterprise end of life isn’t just about installing a new OS — it’s an opportunity to reevaluate how your endpoints are managed, how security is enforced and how users interact with their devices.

Here’s a roadmap your IT team should be following to mitigate your risk:

1. Inventory Your Devices and OS Versions

You can’t migrate what you haven’t identified. Start by building a comprehensive inventory of all endpoints across your organization. Ask yourself:

• • Which devices are running Windows 10?
  • What specific versions (e.g., 21H1, 22H2) are installed?
  • Which ones are eligible for an in-place upgrade vs. hardware replacement?

Tools like Microsoft Endpoint Manager, System Center Configuration Manager (SCCM) or Azure Arc can help automate this step.

2. Identify At-Risk Machines

Focus on endpoints running Windows 10 22H2 or earlier. It is the final supported feature release, and no newer updates will arrive before end of life. Devices on older versions like 21H2 or 20H2 are already in out-of-support territory and should be a top priority.

Sometimes, older hardware may not meet Windows 11’s minimum requirements, such as TPM 2.0 or specific processor models. In these cases, hardware refresh planning should begin immediately.

3. Plan for Upgrades or Replacements

Once your team has identified which machines are running Windows 10 (especially those on the final supported version, 22H2), the next step is to evaluate upgrade options and make strategic decisions about each endpoint. Organizations generally have three choices: in-place upgrades, device replacements or new device provisioning using modern deployment tools.

If a device meets Windows 11’s system requirements — like a supported CPU, TPM 2.0 chip and Secure Boot — it can be upgraded in place. This is the quickest option, letting you keep user data, profiles and apps while moving to the new OS with minimal disruption. Still, you’ll need to test your applications to make sure everything runs smoothly after the upgrade.

Companies will need to replace older devices that do not meet Windows 11 requirements. These legacy systems often lack the hardware-level security needed to support modern threat protection. Rather than trying to force upgrades on unsupported hardware, it’s more effective to use this moment to refresh aging machines. This approach helps standardize your fleet and improve end-user performance.

If acquiring new hardware, consider using Windows Autopilot and zero-touch enrollment capabilities to streamline provisioning. These tools allow IT teams to configure and deploy devices with minimal hands-on effort, making supporting distributed teams or remote workers easier. Autopilot also integrates well with Microsoft Intune and other modern device management platforms, helping IT enforce policies and configurations automatically when a device is first powered on.

Don’t delay this process until the last minute. Many organizations learned the hard way during the global chip shortage that supply chain disruptions can leave IT departments scrambling. Waiting until mid-2025 to begin sourcing hardware could expose you to product backlogs, long lead times and inflated pricing. Licensing models may also change as Windows 10 nears retirement, making upgrades more costly or more complex.

Starting early gives you time to test, train and transition on your own schedule — rather than being rushed into risky or reactive decisions. It also opens opportunities to negotiate pricing, phase rollouts by department and take advantage of incentives offered by Microsoft partners or OEMs looking to assist with mass migrations.

4. Test Applications and Compatibility

Even if your devices meet Windows 11 requirements, your apps may not. Create a testing environment that mirrors your production environment and evaluate:

• • Line-of-business applications
  • Antivirus and security tools
  • VPNs, printers and drivers
  • Custom internal software

Use Microsoft’s App Assure program or the Compatibility Test Kit if you anticipate issues.

5. Build and Communicate a Migration Timeline

Once testing is complete, build a realistic migration schedule and communicate it across teams. Executives, department heads and end users should all know what to expect.

Key details should include:

• • Migration start and end dates.
  • Training or documentation for users.
  • Support resources for troubleshooting.
  • Device backup and data preservation steps.

Long-Term Considerations

While upgrading from Windows 10 is an urgent need, it’s also a strategic opportunity. When done right, this transition can help modernize your IT infrastructure and improve endpoint security.

Evaluate Modern Endpoint Management Tools

If your current processes are heavily manual or legacy-driven, migrating to Windows 11 is a good time to adopt modern tools like:

• Microsoft Intune for mobile and cloud-first device management.
• Windows Autopilot for zero-touch provisioning.
• Conditional access and Azure AD to strengthen identity-based controls.

These tools reduce administrative overhead and support hybrid/remote work environments more effectively.

Leverage the Upgrade to Improve Security Posture

Migrating to Windows 11 isn’t just about keeping systems up to date — it’s a critical move toward strengthening your organization’s overall security posture.

Windows 11 introduces several advanced security features that go well beyond what Windows 10 offers. These include hardware-based isolation enabled by TPM 2.0, the Microsoft Pluton security processor on supported devices and enhanced protections like Secure Boot and virtualization-based security (VBS), which help prevent kernel-level attacks. Windows 11 also adds phishing protection through Smart App Control, which blocks untrusted or malicious apps before they can execute.

Look Ahead to Windows 11 End of Life

Planning for upgrades shouldn’t end with Windows 10. Microsoft has already announced that Windows 11 21H2 will reach end of life support on October 8, 2024, with mainstream support for other versions phasing out gradually depending on your servicing channel.

For Windows 11 Enterprise and Education editions, each release gets 36 months of support. That means future upgrade planning must become part of your normal IT lifecycle, especially if you’re moving to annual updates.

Red River Can Help You Get Ready

Planning a migration across hundreds or thousands of endpoints is no small task. Red River brings deep experience in enterprise device lifecycle management, Microsoft licensing, cloud readiness assessments and security posture upgrades. Whether you need help planning, deploying or managing the Windows 11 transition, we’re ready to support your goals.

Talk to Red River today to schedule a readiness assessment or migration consultation.

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