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 successfulenterprise-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 Regulatory requirements around data protection and system integrity won’t make exceptions for outdated infrastructure.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 If you scramble to deploy last-minute OS upgrades using outdated or manual processes, your IT team will be stretched thin.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.
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.
Salamon, J. (2025, June 30). It’s the end of support for Windows 10. Do you feel fine? or will you be fined? https://blog.quest.com/its-the-end-of-support-for-windows-10-do-you-feel-fine-or-will-you-be-fined/
