Microsoft will officially stop free security updates for Windows 10 on October 14, 2025, leaving businesses and users with a choice: upgrade, pay for extended updates, or risk running an unsecured system. With nearly 70% of Windows users still on Windows 10, the decision brings both challenges and cost implications.

Windows 11’s defining feature is its integration of artificial intelligence (AI), particularly through tools like Copilot, a virtual assistant designed to enhance productivity with smart search capabilities and task automation. Copilot is part of Microsoft’s broader effort to make AI a core part of its operating systems.

However, some users are wary, fearing increased data collection and reliance on automated systems. This skepticism is a factor driving businesses and individuals to stick with Windows 10 for as long as possible.

When the time limit imposed by Windows 10 expires, devices will be vulnerable to new threats as there will be no more free security updates. While Microsoft offers Extended Security Updates (ESU) licenses to help organizations manage the transition, the escalating costs—starting at $61 per device in year one and reaching $244 by year three—make it an expensive stopgap solution.

“Extended Security Updates are not intended to be a long-term solution but rather a temporary bridge,” Microsoft explained in a blog post. “You can purchase ESU licenses for Windows 10 devices that you don’t plan to upgrade to Windows 11 starting in October 2024, one year before the end of support date.”

Many users also hesitate to switch to Windows 11 due to the hardware requirements. Microsoft’s newest OS requires relatively modern hardware, including Trusted Platform Module (TPM) 2.0 chip and processors released after 2018, which excludes many existing PCs from a straightforward upgrade. The necessity for modern hardware has alienated users with older machines, forcing them to choose between upgrading their PCs or looking for alternatives. Some have turned to Linux, an open-source operating system that has gained traction for its flexibility and community-driven support.

Microsoft’s ambition leans into a trend toward intelligent computing,  apparent with Copilot and their AI-enhanced search features, where future computers will be able to assist users through AI-powered predictions. Yet not everyone is on board with these changes, with many citing problems about privacy and the learning curve of adopting these workflows.

The integration of AI into Microsoft’s ecosystem adds a new dimension to the Windows 11 upgrade decision. While businesses can buy time with extended support for Windows 10, the rising costs mean the transition is inevitable. Users will need to weigh the benefits of AI-driven computing against the risks of staying on unsupported systems. Whether they embrace Microsoft’s new vision or explore alternatives like Linux, one thing is certain: AI is no longer optional in this new frontier.