Windows 10 is on the clock. While the 14th of October 2025 might still feel like a distant deadline, the reality is that it’s just around the corner when it comes to enterprise planning. But there’s more to it than just patch updates.
This shift is a pivotal moment for organisations to rethink their IT strategy, hardware readiness, compliance stance, and employee experience. While you may have seen and read other articles about Windows 10 end of support (EOS), we wanted to make it very clear what you must consider to be prepared.
The countdown to 14 October 2025 is more than a milestone, it marks a turning point in cyber risk exposure for any organisation still running Windows 10. After this date, Windows 10 will no longer receive security patches or support as part of standard servicing. This leaves your organisation increasingly vulnerable to cyber attacks, with no new fixes for emerging threats.
Large-scale migrations take time, so the clock really is ticking. Waiting too long to act may lead to rushed deployments, unexpected costs, and significant disruption. This isn’t just a technical deadline; it’s a strategic one.
For organisations unable to complete a migration before the deadline, Microsoft offers an Extended Security Updates (ESU) program. But it doesn’t come cheap. In year one, the cost is $61 per device, doubling in each subsequent year to reach $244 per device by year three. The fees are also cumulative, so if a company joins in year two, it must pay the year one and year two fees. This is not a long-term solution. It’s a stopgap at best and a budget-buster at worst.
More critically, ESUs don’t include feature updates, performance improvements, or innovation. In short, you’re paying more just to maintain the status quo, while still falling behind.
Upgrading to Windows 11 isn’t as simple as clicking ‘update now’. Many existing devices don’t meet the minimum requirement, particularly around CPU compatibility and Trusted Platform Module (TPM) 2.0.
Estimates suggest that 30–40% of devices in the market today won’t meet these requirements. While it’s technically possible to install Windows 11 on unsupported devices, doing so introduces performance instability and additional management complexity, risks few organisations can afford.
Running an unsupported operating system poses not only security concerns but also serious compliance risks. Regulatory frameworks such as the GDPR (General Data Protection Regulation), HIPAA (Health Insurance Portability and Accountability Act), and ISO standards (International Organization for Standardization) often mandate up-to-date software and patching practices.
Operating on outdated platforms can also lead to failed audits, financial penalties, and reputational damage, not to mention the potential loss of trust from customers and partners.
Upgrading isn’t just about plugging security holes. Windows 11 introduces a host of features designed to improve user experience and productivity:
These are not gimmicks, they are practical enhancements that make your teams more efficient and more satisfied with their work environment.
Yes, upgrading your entire organisation can feel overwhelming, but it doesn’t have to be done in one massive wave. A phased rollout allows you to prioritise critical systems, test new environments, and manage budgets more effectively.
Begin with a thorough hardware inventory and compatibility assessment, which Data#3 can help with. From there, develop a tiered deployment plan that aligns with business priorities. Start with pilot groups, gather feedback, and refine the process before wider rollout.
While delaying action might seem like a cost-saving tactic in the short term, it often leads to:
In contrast, organisations that begin planning now can make better informed, strategic decisions. They can budget effectively, choose the right solutions, and execute transitions with minimal disruption.
Remember the lessons of the Windows 7 EOS? Many who waited too long faced outages, rushed deployments, and stressed-out teams. Let’s not repeat history.
Technology is only part of the equation. The other half? People. Both are equally essential to every organisation. Making a smooth transition to Windows 11 hinge on how well your organisation manages change.
This includes:
When employees feel informed and empowered, adoption improves, resistance drops, and productivity rebounds faster.
The Windows 10 EOS is more than a technical milestone, it’s a strategic opportunity. Whether you’re planning a full Windows 11 migration, exploring a hybrid model, or considering alternative approaches, the time to start is now. Because doing nothing? That’s the most expensive option of all.
The Data#3 and Microsoft partnership has been in existence since 1994; Data#3 has the tools and expertise to guide your Windows 11 migration end to end. We hold the highest Microsoft accreditations and work with customers across the full ecosystem, from cloud and data centre to security and end user environments.
We have a range of services to support your migration:
Requirements and discovery workshop
Application compatibility testing and remediation
Proof of concept (POC)
Infrastructure modernisation
Deployment of modern management tools
User training and change management support
Whether you’re ready to start or just beginning to assess your options, now is the time to act.