Preparing for Windows 10 End of Life: A Strategic Guide for MSPs

Windows 10 will officially reach its end of support on October 14, 2025. While this may seem distant, the reality is that planning and execution must start now to ensure smooth transitions for clients. With tariffs being implemented, this is a time of economic uncertainty which will likely have a large impact on many small and medium size businesses.

This massive shift is not just about upgrading systems; it's about protecting client environments, managing operational risks, and maintaining trust as a strategic advisor. Leveraging ITIL4's Change Management process can provide the structure needed to navigate this critical change efficiently. Below is our best-practices and recommended approach MSPs can take to prepare for Windows 10 EOL, using strategic business reviews, client segmentation and personas, project planning, and proactive communication to lead the way.

Why the push?

While I’m sure I don’t need to explain the technical why or how to you, explaining to your clients that Microsoft's announcement means no security updates, patches, or technical support after the EOL date, and exposing outdated systems to significant cybersecurity risks is critical. Research shows that unpatched systems are three times more likely to suffer major breaches. Additionally, about 32% of business PCs are over four years old, and only 55% of those are expected to meet Windows 11 hardware requirements without upgrades (Enterprise Apps Today). Further, IBM has reported that outdated systems have a 74% higher breach risk (https://www.ibm.com/security/data-breach) on unpatched and outdated software. While Microsoft has allowed the bypass of TPM 2.0, it isn't without risk as outlined by Microsoft below.

Critical Notes from Microsoft:

• No Security Guarantees: Devices bypassing TPM 2.0 lose critical security features like Pluton and Secured-Core PC protections.
• Update Risks: Microsoft reserves the right to block updates for non-compliant devices (e.g., KB5029351 blocked some bypass methods).
• Compliance: Only recommended for testing, not production environments.

Without early action, MSPs risk overwhelming their teams and providing a subpar client experience. Planning now ensures clients have the time and budget to make informed decisions and allows MSPs to manage the workload in a structured, high-quality way.

Change Management

Change Management, as defined by ITIL4, provides a structured approach to managing changes with minimal disruption. For Windows 10 EOL, this framework ensures that all planning, communication, and project execution are documented, approved, and tracked. While minor hardware replacements might not need full change management, major initiatives like OS migrations absolutely do.

Strategically Plan for Strategic Business Reviews (SBRs)

Strategic Business Reviews (SBRs) are essential touchpoints to position Windows 10 EOL projects. Not every client will need quarterly reviews. We recommend scheduling SBRs based on Monthly Recurring Revenue (MRR) and client segmentation.

If you don't yet have a client segmentation framework or a policy governing SBR frequency, now is the time to build one. Start by listing all your clients along with their MRR. Then determine logical thresholds for how often you should meet with each tier. Here's a sample breakdown you can adapt:

I often get asked why we recommend this approach. The short answer is simple: the larger the client’s MRR, the more endpoints, projects, security needs, and technology assets you manage. Tier 1 clients often have ongoing initiatives that require frequent strategic discussions. Smaller clients have fewer moving parts and typically tighter budgets, meaning their technology environments may be more stable and changes are less frequent. Matching the cadence of your reviews to the complexity and scale of each client ensures you’re allocating your resources effectively while still providing high-value advisory services to every client segment

What is a Client Persona and Why Does it Matter?

Using Client Personas and User Stories can further enhance messaging and objection handling. A client persona is a semi-fictional representation of your customer based on real data, observed behaviors, and patterns in communication, decision-making, and buying motivations. It’s more than a demographic snapshot, it’s a practical tool to help your team anticipate how different types of clients think, what motivates them, and how they are likely to respond to change.

When preparing for Strategic Business Reviews, especially around initiatives like Windows 10 EOL, having client personas in place can dramatically improve how you communicate your message. Personas help you frame your conversation in a way that resonates with each client's values and concerns. For example, an executive in healthcare is focused on compliance and risk may need to hear about exposure, vulnerabilities, and liability, while a cost-conscious small business owner in finance will care more about cash flow and operational disruption.

By understanding these personas, your team can:

• Predict client objections before the meeting and preemptively address them in your presentation of the solution
• Tailor recommendations to align with the client's business’s priorities, including tiered approaches
• Prepare responses that feel personalized rather than templated
• Build trust faster by speaking the client's language

Developing just a few key personas, like the Security-Conscious Executive in Healthcare, the Cost-Conscious Owner in Finance, can help your entire team approach each SBR with clarity and confidence. These profiles can guide your prep, shape your SOWs, and improve how you present quotes and timelines.

Preparation Steps for Strategic Business Reviews

Pre-SBR Preparation

Before walking into a Strategic Business Review, preparation is critical. Use your RMM toolset to audit client devices and generate reports that clearly flag non-compliant hardware. Devices that do not meet Windows 11 requirements, such as lacking TPM 2.0 or being more than four years old, should be categorized and visually identified in red.

Group devices into two buckets:

• Upgradeable: Systems that meet Windows 11 specs
• Replace: Systems past lifecycle, or unsupported

Then prepare templated materials that you can quickly customize for each client:

• Scope of Work (SoW): Define what’s in scope, exclusions (like legacy apps), and proposed timelines.
• Quotes: Pre-build project estimates, e.g., "$1,200/device, including migration and 1-year warranty" This ensures you are quickly able to adjust and send out the final quote.
• Knowledge Base (KB): Have articles ready such as “Navigating Windows 11’s Start Menu” or “Pinning Legacy Apps”. Having a knowledge base allows clients to search and find answers themselves which can reduce support tickets and calls by up to 30%.

Finally, decide internally how to address unsupported devices: Will you decline support entirely or increase service pricing to account for the added risk and complexity of managing an unsupported operating system?

Conducting the SBR

During the Strategic Business Review, when done correctly, there should be a two way conversation with the client speaking the majority of the time. Remember, you're there to help them achieve their business objectives while keeping them informed of risks and improvements along the way. Their technology should help them achieve their goals and operate smoothly.

The SBR is no different, however, when it comes time to address the Windows 10 EOL. Make sure to begin with a strong emphasis on "why" this conversation matters by highlighting the risk of unpatched systems and the operational impact of unsupported hardware. Present specific device recommendations and outline upgrade or replacement pathways clearly. It’s important to listen to the client’s concerns without pushing back immediately. Take detailed notes on objections, so that you can craft thoughtful, well-reasoned follow-ups later. Acknowledge and respond to the objections but avoid trying to aggressively overcome them as it may come across in unintended ways such as a push for sales. Using the client personas can help prepare and address these concerns before they are brought up.

Post-SBR Follow-Up

Within 24 hours of the meeting, send a comprehensive follow-up package to the client. This should include the Scope of Work, the formal quote, and a detailed response to any objections or questions raised. Offer the opportunity to schedule a short follow-up call to review the details. Confirm decision-making timelines and ask the client for the best time to follow up.

NOTE: Clients generally don't want to see tables of ticket metrics. Giving them a detailed report with the important information in an easily digestible format in the first few pages as an overview will enable them to hone in on the information they need quickly. They can flip through the details in the following pages if needed.

From Approval to Execution

Internal Rollout Planning

Once the client approves the project, the next step is a detailed rollout plan. Larger organizations may require phased upgrades over several weeks, while smaller businesses might handle transitions in a single day. Always consider client industry cycles; for instance, avoid rolling out upgrades for accounting firms during month-end or tax season. Thoughtful scheduling avoids stress and improves project outcomes.

Client Communication Strategy

Effective communication can make or break the project. Send detailed pre-upgrade emails outlining exactly what to expect—the date, time, duration of the upgrade, primary contact for support following the upgrade and what actions users must take, such as ensuring devices are plugged in, powered on, and connected to the internet. Stress the importance of not powering down devices during the upgrade to avoid corruption, and also to avoid downtime during the next startup. Additionally, provide links to self-service resources for basic troubleshooting after the update.

Execution Day Support

Schedule the actual upgrades mid-week, generally Wednesdays or Thursdays tend to be optimal, to minimize ticket volume interference. Assign technicians to standby roles with clear instructions: prioritize urgent post-upgrade support but remain available for quick ticket handling between those calls. Dispatch should be informed about who is on standby, ensuring fast escalation paths if needed. Even if calls are light, technicians must stay engaged but available for transition support.

Key Points to Remember

• Do not rush massive upgrades; stagger and plan for consistent quality.
• Respect client operational cycles when scheduling upgrades.
• Communicate proactively and clearly throughout the entire process.
• Document every step for transparency and continuous improvement.

Conclusion

Windows 10 EOL is a major event that MSPs cannot afford to approach reactively. By planning ahead with structured Change Management processes, segmenting clients strategically, building proactive support resources, and communicating clearly, you can turn this industry-wide challenge into a showcase of your operational maturity, excellence, and value. Starting now ensures that you control the pace, minimize disruptions, and strengthen client trust when it matters most.

If you would like help preparing client segmentation, project templates, or SBR strategies for your team please reach out, we're here to help guide your success through this transition. Book a 30-minute consultation to build your Windows 10 EOL playbook and standardize how you execute Strategic Business Reviews. Let’s turn this deadline into your next revenue stream!

Additional Resources

Additional Resources

• ITIL 4 Change Enablement Guidelines
• Microsoft’s Windows 10 EOL Advisory
• 74% higher breach risk