October 14, 2025, marks the official end of support for Windows 10. That date is a little too close for comfort when you consider the complexity and scope of a successful enterprise-wide operating system (OS) migration.
This isn’t just a routine IT upgrade. This is a business continuity challenge that requires immediate attention from executive leadership. Delaying your planning process can lead to cascading risks across operations, security and compliance. You need to begin now because the operational and financial implications of inaction will only increase with time.
What’s at stake for your business with Windows 10 end of support
Failing to act on the Windows 10 end-of-life deadline is not a passive decision—it’s an active risk. According to Gartner, 80% of total IT costs occur after the initial purchase, largely due to support, maintenance and downtime. The consequences of waiting are significant as running unsupported OS versions after October 2025 will add to your cost burden substantially.
Security vulnerabilities will rise. Once support ends, Windows 10 devices will no longer receive security updates. Multiple studies have shown that endpoints are the entry point for up to 90% of successful cyberattacks and as many as 70% of successful data breaches. If your endpoints are running an unsupported OS, your attack surface grows overnight. Regulatory requirements around data protection and system integrity won’t make exceptions for outdated infrastructure.
Compliance penalties will follow. If you’re in a regulated industry like finance, healthcare, or government, or working with organizations that are, unsupported endpoints could put you out of compliance. This isn’t just a tech problem; it’s a legal one.
Manual migrations carry hidden costs. If you scramble to deploy last-minute OS upgrades using outdated or manual processes, your IT team will be stretched thin. You’ll likely miss critical deployment windows and introduce errors. The unbudgeted labor hours and disruption to user productivity will far exceed the cost of early, automated planning.
Operations will be disrupted. Without coordinated planning, users could lose access to critical applications due to compatibility issues. Business services could be slowed or halted entirely. Reactive migration often means prioritizing speed over reliability… and that’s when mistakes happen.
The Windows 11 leap: What makes this upgrade different
Windows 11 introduces fundamental shifts that make this upgrade more complicated than prior transitions. For many enterprises, this is not just a software update, it’s a hardware overhaul. Microsoft has raised the bar on minimum system requirements, and some reports are stating that over 40%, or roughly 400 million, Windows 10 devices will be ineligible for an upgrade.
This requires a complete hardware inventory and compatibility analysis. It also means potential new device purchases must be within your fiscal budget. Delaying this analysis pushes you into a corner where procurement and migration timelines collide, and that leads to missed deadlines and unnecessary costs.
You also need time to test your application portfolio. Many legacy or line-of-business applications may not function as expected on Windows 11. Application remediation is not a switch you flip… it’s a phased, strategic process.
And then there’s workforce impact. Every migration introduces change. Without proper communication, training and support, your employees may face productivity loss and frustration. As an executive leader, you must sponsor the change not just from a technology perspective, but from a change management perspective also.
Delaying now means paying more later
It’s tempting to defer action when no crisis feels imminent. But waiting to address Windows 10 end of support until the last minute won’t just compress your schedule, it will inflate your costs.
If you start planning now, you can:
- Align procurement with existing budget cycles
- Avoid emergency hardware purchases at premium prices
- Reduce labor costs with automation
- Limit downtime through phased rollouts
- Minimize risk of security breaches or compliance violations
- Preserve productivity with proactive user training
Forrester has noted that organizations who embrace automated migration tools and phased deployment models can save up to 40% in operational costs compared to those using manual, reactive approaches.
The financial risk of ignoring the Windows 10 end-of-support deadline is measurable… and avoidable.
What about Microsoft’s ESU Program?
Using Microsoft’s Extended Security Updates (ESU) Program for Windows 10 can be tempting but it may not be a great business decision for several reasons, especially when viewed from a strategic, financial and operational perspective. Below are the key reasons.
High and escalating costs. The ESU program is expensive, with costs doubling each year for businesses. Pricing starts at $61 per device for the first year. $122 per device for the second and $244 per device for the third year, totaling $427 per device over three years. This cumulative cost structure means businesses cannot skip earlier years to save money; enrolling in year two requires paying for year one as well.
Limited scope of updates. The ESU Program only provides critical and important security updates as defined by Microsoft’s Security Response Center. It does not include new features, non-security fixes, bug fixes or general technical support.
Missed opportunities with Windows 11. Windows 11 offers advanced security, productivity, and AI-driven features (e.g., Copilot+), as well as improved performance for hybrid work environments. Business opting for ESU will miss out on these benefits, which could enhance efficiency and competitiveness.
Will you wait for a crisis or take command and control now?
If you’re in a senior IT, operations or compliance role, here’s how you can take ownership today:
- Initiate an executive-level conversation about the end-of-support timeline and its risks
- Direct IT teams to begin a full asset and compatibility assessment
- Ensure budgets reflect hardware refreshes, tool investments and training resources
- Establish cross-functional governance to guide the migration project
- Define key metrics such as device readiness, app compatibility, user satisfaction and deployment success
- Communicate openly and frequently with business units to maintain transparency and trust
The transition to Windows 11 will happen, one way or another. The only question is whether it will happen on your terms… or under crisis conditions.
Your step-by-step action plan for OS migration
A successful migration isn’t driven solely by IT; it’s a collaborative business initiative. Here’s what a best-practice plan should include:
1. Executive sponsorship.
Secure visible, ongoing support from senior leadership. Treat this as a business transformation project, not an IT refresh. Leadership sets the tone and helps ensure organization-wide alignment.
2. Comprehensive inventory and readiness assessment.
Assess every endpoint for hardware compatibility, usage patterns, and criticality. Identify what can be upgraded, what must be replaced, and what requires further analysis. Without a full asset picture, planning is guesswork.
3. Choose your upgrade path.
- In-place upgrade: Retains apps, settings, and files but requires thorough testing.
- Clean install: Wipes the system for a fresh start, ideal for older or problematic devices.
- Image-based deployment: Uses Microsoft or third-party tools to automate the process of installing the operating system and applications on multiple computers.
4. Application testing and remediation.
Conduct thorough testing of enterprise applications, especially those built in-house or tailored to specific workflows. Document which apps need updates or reconfigurations for Windows 11 compatibility.
5. Phased deployment plan.
Segment your organization into logical groups for staged rollouts. Begin with pilot users, refine the process, and then expand. Prioritize mission-critical users with the most complex needs.
One solution. Many workloads.
6. Contingency planning.
Prepare for potential issues: hardware shortages, user resistance, app incompatibilities. Build buffer time into your schedule and identify fallback processes that preserve continuity.
7. User communication and training.
Keep users informed throughout the migration journey. Clear timelines, expectations and support channels will minimize disruption and improve satisfaction. Consider offering brief training sessions or self-help materials to ease the transition.
Final thoughts
Windows 10 end of support requires more than a routine IT upgrade; it’s a strategic moment that tests your organization’s readiness for change, risk tolerance and leadership vision. The enterprises that succeed will be those who act early, plan thoroughly and lead boldly.
Don’t wait any longer to start planning your migration strategy. October will be here before you can blink. Begin now, while you still have the luxury of time to do it right.
