Sourcepass Blog

Executive Guide: Balancing Cost, Risk, and Timing for Your Windows 10 Strategy

Written by Alex Davis | Oct 01, 2025

Microsoft will officially end support for Windows 10 on October 14, 2025. After this date, devices that continue running Windows 10 without Extended Security Updates (ESUs) will no longer receive critical patches. For executives, the question is not whether to act, but how to balance cost, risk, and timing when deciding on the future of your organization’s IT environment.

This guide outlines the trade-offs business leaders need to evaluate when considering Windows 10 ESUs versus an immediate upgrade to Windows 11.

 

Understanding the Windows 10 Deadline

Windows 10 has been a stable and widely adopted operating system for years, but its lifecycle is coming to an end. Once Microsoft discontinues support:

  • No more free security updates

  • Increased exposure to cyberattacks and compliance risks

  • Pressure to either migrate quickly or purchase ESUs as a temporary safety net

 

What Are Windows 10 Extended Security Updates (ESUs)?

ESUs are a paid Microsoft program that delivers only security updates after October 2025. They are available for:

  • Windows 10 Pro, Enterprise, and Education editions

  • Devices running version 22H2

  • Purchases through Microsoft, CSP partners, OEMs, or resellers

While ESUs provide short-term protection, they do not add new features, performance improvements, or non-security fixes.

 

The Cost Equation

ESUs are sold in 12-month increments and priced per device. The cost doubles each year, making long-term reliance financially challenging:

  • Year 1: $61 per device

  • Year 2: $122 per device

  • Year 3: $244 per device

By comparison, a well-planned migration to Windows 11 is a one-time project investment that avoids escalating ESU costs.

 

The Risk Factor

Remaining on Windows 10 without support introduces significant risk. Even with ESUs, businesses face:

  • Rising attack surfaces due to outdated architecture

  • Limited ability to adopt modern security and compliance standards

  • Operational inefficiencies from delaying modernization

Executives must weigh whether the temporary protection from ESUs is enough to offset these risks.

 

Timing Considerations

Every organization has different IT readiness. Timing decisions often depend on:

  • Infrastructure maturity: Are your devices and applications compatible with Windows 11?

  • Budget cycles: Can you allocate funds for a migration this year, or do you need to extend your timeline?

  • Operational disruption: Can your teams handle an upgrade project without impacting productivity?

ESUs can buy time, but the timeline should be used strategically, not as an excuse to delay indefinitely.

 

Strategic Options for Executives

Executives generally have two primary options:

1. Upgrade to Windows 11 Now

  • One-time investment with long-term stability

  • Access to modern features, performance, and ongoing support

  • Improved compliance posture

2. Use Windows 10 ESUs as a Short-Term Bridge

  • Keeps systems secure temporarily while planning a migration

  • Adds annual costs that double each year

  • Requires clear communication that this is not the end strategy

 

Executive Recommendation

From a leadership perspective, ESUs should be treated as a contingency plan, not a business strategy. The smarter move is to budget and plan for a Windows 11 upgrade as soon as possible.

A phased approach often works best:

  • Identify and upgrade devices ready for Windows 11 today

  • Apply ESUs to only the legacy systems that truly need more time

  • Establish a clear migration roadmap that completes before ESU costs double or triple

 

Frequently Asked Questions

1. How long can my business stay on ESUs?
Up to three years, ending in October 2028. Costs increase each year.

2. Can Windows 10 Home devices use ESUs?
No. Only Pro, Enterprise, and Education editions are eligible.

3. Will ESUs give my systems new features?
No. ESUs only provide critical and important security patches.

4. Is upgrading to Windows 11 mandatory?
Yes. ESUs are temporary. Every business must eventually migrate to Windows 11 or another supported operating system.

 

Bottom Line

The end of Windows 10 support requires executive-level decision-making that balances cost, risk, and timing. While ESUs offer temporary relief, they are expensive and limited. A proactive Windows 11 migration delivers lasting security, compliance, and performance benefits.

At Sourcepass, we help organizations evaluate their IT environment, build migration roadmaps, and implement either ESUs or full Windows 11 upgrade projects. The goal is simple: keep your business secure and future-ready while minimizing disruption.