Windows 10 EOS Deadline Presents a Critical Opportunity for MSPs to Upgrade Clients and Strengthen Security

As October 17, 2025 approaches, the end of support for Microsoft Windows 10 comes with it. It is an important milestone that many Managed Service Providers (MSPs) need to proactively address with their clients. The transition from Windows 10 to Windows 11 presents both opportunities and challenges, particularly when dealing with organizations that might not prioritize technology upgrades until they face an urgent need. While upgrading to Windows 11 can be relatively straightforward for many systems, the implications for cybersecurity, hardware, and business strategy are far-reaching.

Software vs. Hardware Upgrades

For businesses with relatively new hardware, the shift from Windows 10 to Windows 11 can be a simple process, as most modern systems are compatible with Windows 11’s requirements. Many computers built within the past eight years should have the Trusted Platform Module (TPM) 2.0 chip, alongside other specifications necessary for a smooth transition. This means less downtime, lower costs associated with hardware purchases, and fewer labor hours associated with performing upgrades. N‑able Patch Management makes this an even easier process as it allows you to control when this upgrade occurs.

However, for older Windows 10 computers nearing the end of their life cycle, or lacking TPM 2.0 modules, the upgrade can become more complex. These machines will not support Windows 11, and this poses a challenge for many businesses. On top of this, while upgrading a handful of computers might be manageable, upgrading fleets of machines presents a significant financial burden. Furthermore, the hidden costs, such as compatibility testing, potential software re-licensing, and training for staff on new interfaces, can be daunting for business leaders to engage with when as far as they can tell everything is running just fine.

MSPs often carry the responsible for identifying these older systems and presenting their clients with options. The decision comes down to either investing in new hardware or attempting to extend the life of legacy machines, potentially increasing the risk of running unsupported software.

Resistance to Change

Convincing business leaders to invest in new hardware or upgrades can be a significant challenge. Often, these leaders focus on the immediate bottom line, and if their existing systems are functional, they may not see the urgency in upgrading to Windows 11. They might view the upgrade as unnecessary, especially since the business operations benefits of moving from one operating system to another may not be compelling or readily visible. However, this is where the role of an MSP extends beyond just providing technical solutions; it requires strong advisory, risk management and educational capabilities.

The main challenge lies in communicating the risks that come with running unsupported software. Once Windows 10 reaches end-of-life, Microsoft will no longer provide security updates or patches, leaving systems vulnerable to exploits. Explaining the potential for increased cybersecurity threats—ransomware, phishing attacks, data breaches—and how these vulnerabilities can affect business operations, and help MSPs position the upgrade as a necessary investment rather than an optional expense. In this context, MSPs must shift the conversation from “hardware replacement” to “protecting the business’s future and its data assets.”

Have Conversations Early

It’s an old adage but if a wheel isn’t squeaking then it doesn’t need grease. If a piece of equipment adequately serves its function in the business little attention will be paid to it. This means when you approach a decision maker to inform them that an operating system has been out of support but it still serves its business function just fine they are not likely to be very motivated to replace it since it ‘still works’.

It’s much easier to convince a decision maker of the need to plan for an upgrade of systems that will reach end of support in a year than it is to convince them they need to replace a system that reached end of support a year ago and they have, so far, suffered no impacts to the business from that out of support device.

Balancing Costs and Security

The decision to upgrade should involve a thoughtful risk conversation that balances business operational needs against security. Business leaders often view technology spending as a capital expenditure, and persuading them to allocate budget for an upgrade when existing systems appear to be functioning well can be an uphill battle. However, MSPs can reframe this discussion by focusing on the hidden costs of not upgrading—such as system failures, increased maintenance, downtime, and potential breaches due to security vulnerabilities.

Rather than simply highlighting the immediate costs of upgrading, MSPs should emphasize the costs of not upgrading. Unsupported operating systems often incur far greater expenses when a breach occurs or when legacy systems break down and require emergency fixes or replacements. Presenting data on increased vulnerabilities, compliance requirements, and potential fines for non-compliance can also help drive home the importance of moving off unsupported software.

Future-Proofing with Managed Services

MSPs can take this opportunity to not only assist in the transition from Windows 10 to Windows 11 but also to help clients future-proof their systems. As Windows 11 represents a relatively stable platform with a focus on software over hardware changes, businesses can expect a smoother path for future upgrades. This opens the door for MSPs to offer managed service packages that include regular system assessments, updates, and hardware refresh cycles.

By offering long-term technology planning services, MSPs can help businesses avoid the “boom and bust” cycle of hardware and software replacements. Instead, companies can move toward more predictable, subscription-based service models that spread out the costs of staying current with technology, reducing the shock of major capital expenditures and even transitioning some capital expenditures to operation expenditures.

Conclusion: A Strategic Opportunity for MSPs

The end of Windows 10 support should be viewed as more than just a technical hurdle; MSPs should look at it as a strategic moment to solidify their role as trusted advisors. While upgrading to Windows 11 might seem simple from a technical standpoint, the real challenge can be in convincing business leaders of the importance of proactive investments in technology. MSPs can navigate these conversations by focusing on security, risk mitigation, and the long-term benefits of staying current with supported software.

The October 17, 2025 deadline is fast approaching and the time needed to plan, budget, and execute upgrades is even shorter. MSPs need to be at the forefront of guiding their clients through this transition—one that has implications not just for this particular upgrade project but also for shaping the security and resilience of their client’s business in the future.

Lewis Pope is the Head Security Nerd at N‑able. You can follow him on Twitter: @cybersec_nerd

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