Microsoft’s 2025 Upgrade Push: 5 Smart Moves for MSPs Supporting Clients

Microsoft’s push to retire Windows 10 and complete the shift to Windows 11 by October 2025 affects more than 400 million devices worldwide—and that means managed service providers (MSPs) are on the front lines. While many end users are unaware or hesitant, this looming deadline presents a massive opportunity for MSPs to lead, educate, and deliver.

Here are 5 smart moves MSPs can make now to guide clients through the transition and position their businesses for long-term value.

1. Run a Full Endpoint Audit—And Communicate It Clearly

Start with visibility. You need to know exactly which client devices are still running Windows 10 and how critical they are to operations. An audit allows you to categorize risk, budget needs, and timeframes—and shows your clients you’re ahead of the curve.

MSP Tip: Create a branded “Windows 10 Status Report” for each client. Visual reports help drive urgency and trust.

2. Initiate Upgrade Roadmaps During QBRs

Clients rely on their MSPs for strategic IT guidance. Make Microsoft’s deadline a central topic in upcoming quarterly business reviews. Use the opportunity to scope upgrade plans, hardware refresh cycles, and any compatibility checks needed.

MSP Tip: Present upgrade paths with optional add-ons—like EDR tools, remote monitoring, and cloud backups—for extra margin.

3. Turn Compliance into a Call to Action

In many industries—like healthcare, finance, or legal—running an unsupported OS after October 2025 could trigger compliance issues and insurance exposure. This isn’t just an IT inconvenience—it’s a risk management issue.

MSP Tip: Include Windows 11 compliance checkpoints in your cybersecurity assessments and incident response plans.

4. Bundle the Upgrade into a Broader Security Conversation

The upgrade from Windows 10 isn’t just about staying current—it’s also a chance to modernize. Use this shift as a springboard for talking about Zero Trust, MFA, and advanced endpoint protection. Security sells.

MSP Tip: Offer an “Endpoint Evolution Package” that includes OS upgrades, EDR, user training, and compliance auditing.

5. Make It Easy—Offer Fixed-Fee Upgrade Projects

Many clients fear complexity and unknown costs. Turn your upgrade offer into a fixed-fee service with clear deliverables. By taking the ambiguity out, you’ll increase adoption and show real leadership.

MSP Tip: Create simple upgrade tiers: Basic (OS only), Standard (OS + AV + backup), and Premium (full device lifecycle and support).

Microsoft’s 2025 Windows upgrade deadline doesn’t have to be a headache—it can be a catalyst. MSPs who act now, educate consistently, and wrap upgrades into broader value-added services won’t just meet the moment—they’ll grow from it. This is more than a migration; it’s a relationship-deepening opportunity.