Sticking With Windows 10 Is the Most Expensive Way to Save Money

On October 14, Windows 10 officially reached its end of support. Overnight, millions of business devices crossed an invisible line: they still power on, but they no longer receive Microsoft’s free security updates and technical support that once kept them safe.

For organizations hesitant to move to Windows 11, Microsoft offers a temporary lifeline— Extended Security Updates (ESU) —a paid subscription workaround that provides critical patches for unsupported Windows versions. But that lifeline comes at a steep cost: $61 per device in year one, doubling each year to reach $427 per device over three years. And ESU delivers no new features. No bug fixes. No technical support. Microsoft itself warns the program is meant as a short-term bridge, not a long-term solution.

Meanwhile, the hidden costs begin to stack up—rising cyber risk, stricter audits, and more strain on already stretched IT teams. What seems like a way to save money quickly turns into the costliest path of all.

The real question isn’t “Should we upgrade?” anymore. It’s “How much are we willing to pay—financially and operationally—just to delay?”

Computer screen with Windows 11 loaded

The Real Cost of Standing Still

1. Higher Cyber Risk

Unpatched systems are easy prey. Now that Windows 10 has reached end of support, every new vulnerability discovered creates an elevated exposure point. While ESU provides critical security patches, it does not deliver the full spectrum of updates, leaving gaps that attackers can exploit. Threat actors are expected to stockpile vulnerabilities and reverse-engineer Windows 11 patches to craft attacks that bypass ESU coverage.

The attack surface also stops evolving, making legacy systems prime targets for ransomware, malware, and remote code execution. Even a single unpatched device can act as a foothold for lateral movement within the network or a weak link in the supply chain, exposing the broader business to compromise. In short: delaying migration doesn’t freeze risk—it multiplies it.

2. Tougher Audits & Compliance Risks

Unsupported operating systems create immediate compliance challenges. Most regulatory and security frameworks explicitly require that software be current, patched, and supported. Running Windows 10 past its end of support moves organizations out of alignment with these standards and leaves them vulnerable to audit findings.

Extended Security Updates (ESU) don’t fully solve the problem. Because ESU only delivers critical patches—without quality updates or full support—many auditors will not accept it as a long-term control. That forces organizations to rely on compensating measures and extra documentation, adding time, cost, and complexity to audit readiness.

The risks extend beyond failed audits. Organizations face the possibility of fines, contractual penalties, reputational damage, and even cyber insurance exclusions. Insurers increasingly deny claims or raise premiums when breaches involve unsupported operating systems, making Windows 10 not just a compliance concern, but a business continuity risk.

3. Overworked IT Teams & Stalled Innovation

Keeping Windows 10 alive through ESU doesn’t just strain budgets—it strains people. Help desk tickets rise as legacy systems encounter more compatibility issues. Patch management also grows more complex, with IT teams forced to spend extra time monitoring, testing, and deploying critical updates under ESU’s limited coverage. Hardware limitations add another layer of frustration.

Instead of focusing on modernization, automation, and employee experience, IT staff are forced into a constant firefight of urgent patching and short-term fixes. Research shows

patch delays across Windows devices already average nearly two months, and unsupported systems only make the backlog worse. The result is long hours, rising burnout, and higher turnover as skilled professionals look for opportunities where they can innovate, not maintain outdated infrastructure.

The opportunity cost is significant: every hour spent propping up unsupported systems is an hour not spent advancing digital transformation or improving the employee experience.

Mitigation in Q4: Buy Time Without Buying Trouble

With budgets most likely locked and the calendar winding down, most organizations won’t launch a full Windows 11 migration before year-end. But doing nothing isn’t an option either. The smarter path is mitigation: contain today’s risk while laying the groundwork for tomorrow’s execution.

That looks like four deliberate moves:

1. Scope Extended Security Updates Wisely Treat ESU as a bridge, not a destination. Limit coverage to the endpoints that truly can’t move yet—specialized devices, systems with temporary software dependencies, or machines awaiting refresh. Keep that list small, visible, and tied to leadership oversight. Every ESU enrollment should have a clear rationale, a risk owner, and an expiration date.
2. Document Every Exception Unsupported operating systems are always a red flag in audits. The difference between acceptable risk and unacceptable negligence often comes down to documentation. Record why each Windows 10 device is still in service, what compensating controls are in place, and when the risk will be retired. Maintain patch logs and evidence of controls so that auditors, insurers, and boards see diligence, not drift.
3. Segment Devices for Control and Clarity A comprehensive inventory is essential. Divide endpoints into three cohorts: ready to upgrade, needs refresh, and covered temporarily. This segmentation simplifies planning, prevents blind spots, and makes it easier to phase rollouts. It also helps IT leaders focus resources where they matter most—isolating high-risk devices, refreshing outdated hardware, and upgrading the bulk of the fleet in planned waves.
4. Reclaim Value Through Secure IT Asset Disposition (ITAD) Retiring Windows 10 hardware isn’t just about risk reduction—it’s an opportunity to recover value. Partnering with a certified ITAD provider ensures data is securely destroyed, chain-of-custody is documented, and resale or trade-in proceeds flow back into the budget. Done right, ITAD helps offset migration costs, supports sustainability goals, and eliminates lingering risk from forgotten devices.

From Mitigation to Migration

Mitigation buys time, but it’s not the finish line. Once budgets and timelines open up, organizations need a structured approach to migrate at scale—one that minimizes disruption, maximizes value, and links technical execution to business outcomes.

Here’s what to consider when you’re ready to move:

1. Plan with the End in Mind

Successful migrations begin with clear definitions of success. Establish readiness criteria around hardware compatibility, application stability, user feedback, and business priorities. Set measurable goals—whether it’s reducing security risk, improving productivity, or supporting sustainability reporting.

2. Build a Resilient Migration Program

A phased approach reduces risk. Pilot deployments first, then scale through waves—each one informed by lessons learned. Pair this with strong governance: a steering committee to align IT, security, procurement, and business units, plus transparent dashboards and clear user communications. The right cadence builds momentum and reduces resistance.

3. Optimize Device Lifecycle for Cost and Sustainability

Not every device needs replacement. Use management data to separate upgradeable systems from those requiring refresh. For retired assets, certified IT asset disposition (ITAD) ensures secure data destruction, maximizes resale value, and provides ESG reporting. Refreshing devices also reduces long-term support costs and improves energy efficiency.

4. Choose a Partner Who Goes Beyond Deployment

Windows 11 migration is an inflection point: the chance to retire legacy risk and build a smarter, more secure environment. The right partner brings technical breadth across tools like Intune, Configuration Manager, and Windows Autopatch, while also guiding governance, compliance documentation, and stakeholder communication. They connect the dots between device refresh, secure ITAD, and long-term lifecycle management so the migration delivers lasting business value.

MCPC provides that end-to-end support. With certified Microsoft consulting, enterprise-scale program management, and a proven track record in device lifecycle services, MCPC helps organizations turn migration into transformation—reducing risk, optimizing costs, and creating a more secure, productive environment for employees.

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