The October 14, 2025 end-of-support deadline for Windows 10 is not merely a calendared event — it is a commercial and technical inflection point that hands managed services providers (MSPs) a unique, high-margin growth opportunity to lead migrations, manage risk, and convert one-off refresh activity into long-term managed relationships. ControlUp’s large-scale readiness data and Microsoft’s own lifecycle guidance make the stakes crystal clear: a significant portion of enterprise endpoints remain on Windows 10 as the clock winds down, and many of those devices are operationally ready but stalled by execution friction. MSPs that pair rigorous readiness assessments, Digital Employee Experience (DEX) telemetry, and human-centered rollout design can turn migration activity into recurring revenue and strategic advisory engagements.
Microsoft has fixed the end-of-support date for Windows 10 at October 14, 2025. After that date Microsoft will stop shipping routine security updates, feature updates and general technical assistance for mainstream Windows 10 editions; customers have the option to enroll eligible machines in the Windows 10 Consumer or commercial Extended Security Updates (ESU) program as a time-limited bridge. That technical reality alters threat models, compliance postures, and support economics across every industry that depends on Windows endpoints.
StatCounter and independent telemetry show the migration is underway but incomplete: Windows 11 overtook Windows 10 in mid‑2025 as the most common Windows version in web-tracking data, yet tens of millions of business devices remain on Windows 10 in enterprise estates. Those devices will continue to boot after October 14, 2025 — but they will increasingly become targets for attackers and sources of compliance exposure for regulated organizations. The combination of telemetry variance, regional differences, and organizational complexity is why channel and MSP leaders must treat end-of-support as a programmatic, not one-off, opportunity.
Specific vertical notes:
Recommended immediate actions:
Conclusion
Windows 10’s October 14, 2025 end-of-support is both a deadline and a door — a deadline that creates risk for organizations that delay, and a door to new recurring revenue and advisory relationships for MSPs that deliver migration outcomes with measurable employee experience improvements. The market is mature enough for partners to sell beyond the patch: the winning MSPs will combine readiness discovery, DEX-based execution, and aftercare optimization to turn a one-time migration into a strategic, multi-year managed services relationship.
Source: Managed Services Journal https://managedservicesjournal.com/...of-support-into-your-msps-next-growth-driver/
Microsoft has fixed the end-of-support date for Windows 10 at October 14, 2025. After that date Microsoft will stop shipping routine security updates, feature updates and general technical assistance for mainstream Windows 10 editions; customers have the option to enroll eligible machines in the Windows 10 Consumer or commercial Extended Security Updates (ESU) program as a time-limited bridge. That technical reality alters threat models, compliance postures, and support economics across every industry that depends on Windows endpoints. StatCounter and independent telemetry show the migration is underway but incomplete: Windows 11 overtook Windows 10 in mid‑2025 as the most common Windows version in web-tracking data, yet tens of millions of business devices remain on Windows 10 in enterprise estates. Those devices will continue to boot after October 14, 2025 — but they will increasingly become targets for attackers and sources of compliance exposure for regulated organizations. The combination of telemetry variance, regional differences, and organizational complexity is why channel and MSP leaders must treat end-of-support as a programmatic, not one-off, opportunity.
Overview: the commercial opportunity for MSPs
The Windows 10 sunset creates multiple adjacent revenue opportunities for MSPs:- Short-term migration projects: readiness assessments, application compatibility testing, in-place upgrades, staged device refresh programs.
- Medium-term advisory and modernisation: DaaS, VDI refreshes, identity / Zero Trust hardening, cloud desktop pilots (Windows 365 or AVD).
- Recurring managed services: DEX-based monitoring, OS lifecycle management, patching and security operations for heterogeneous estates.
- Sustainability and disposal services: trade-in facilitation, secure data-wiping and e‑waste handling — increasingly important for corporate ESG.
The business risks if you do nothing
Leaving significant numbers of endpoints on an unsupported OS is a business risk, not just an IT problem. Key risks include:- Security exposure: missing OS-level patches expands exploit windows for ransomware and targeted attacks. ESU is a temporary costly bandage at best.
- Compliance and insurance gaps: auditors and insurers increasingly expect supported software baselines; unsupported OSes can be flagged as control failures.
- Operational instability: older drivers and app incompatibilities become harder to manage over time as ISVs reduce testing on legacy platforms.
- Rising total cost of ownership (TCO): emergency break/fix, extended ESU spend, and delayed refreshes compound costs over multiple fiscal years.
Why the migration gap exists — and the role MSPs must play
ControlUp and other telemetry providers show a recurring pattern: a high percentage of Windows 10 devices are technically ready for Windows 11, but migration completion lags. Reasons include:- Application and peripheral compatibility concerns.
- Decentralized decision-making and budget cycles.
- Large estates with thousands of devices requiring phased pilot and staged rollouts.
- Regulatory or sector-specific validation requirements (finance, healthcare, government).
- User disruption fears and insufficient internal project capacity.
Use DEX telemetry as your differentiator
Digital Employee Experience (DEX) platforms provide the insights MSPs need to run migration programs confidently:- Device readiness mapping: identify upgrade-eligible machines versus those requiring replacement.
- Application dependency discovery: detect in-use binaries, background services, and driver footprints that must be remediated or repackaged.
- Real-time performance baselining: measure pre and post-upgrade performance to quantify uplift (or regressions).
- Embedded feedback loops: collect user surveys and sentiment to refine pilot scopes and user training.
Designing an MSP migration offering that wins
A market-winning offering must combine technical rigor with user empathy and commercial clarity. Below is a practical, client‑facing migration product model MSPs can use.Core components
- Readiness Assessment (fixed-fee)
- Inventory and hardware capability scan
- App dependency report and risk categorization
- Regulatory and compliance impact assessment
- Pilot & Remediation (time-and-materials or fixed)
- Pilot of representative user groups and business-critical apps
- App repackaging and driver validation
- Firmware and BIOS validation with OEMs where required
- Staged Rollout (subscription + per-seat migrations)
- Phased deployment by site or business unit
- Automated in-place upgrades or staged reimaging via Autopilot/Intune
- Day‑one support and rollback runbooks
- DEX Continuous Monitoring (recurring)
- Post-migration performance and UX monitoring
- Quarterly optimization reports and SLA-backed remediation
- Modernization add-ons (upsell)
- Desktop-as-a-Service pilots (Windows 365)
- Endpoint protection and Zero Trust hardening
- Device lifecycle and trade-in management
Pricing and packaging guidance
- Offer a one-off readiness assessment that generates a prioritized remediation list; price this to be low-friction and sales-enabling.
- Bundle migration hours into subscription tiers that include a guaranteed number of upgrades per quarter.
- Price DEX monitoring as a monthly subscription with explicit KPIs — e.g., Mean Time to Remediate (MTTR) for post-upgrade incidents.
- Include “ESU advisory” as a temporary consult for clients unwilling/unable to migrate immediately: evaluate cost vs. risk and recommend the minimal ESU coverage required.
Execution playbook: five practical steps MSPs must operationalize
- Run a comprehensive, agent-based discovery to map true upgrade readiness and app dependencies. Don’t trust only vendor claims of “readiness.” Use DEX to quantify the effort.
- Build a pilot that mirrors the largest friction points (line-of-business apps, specialist peripherals, remote users). Validate rollback and incident playbooks before mass deployment.
- Use staged rollouts with automated telemetry gates — let DEX determine the cadence by surface-level impact, not calendar pressure.
- Offer end-user experience services: communications templates, change champions, targeted training, and rapid “white-glove” remediation for power users.
- Convert one-off projects to ongoing managed services: post-migration DEX monitoring, patch assurance, and a device lifecycle plan tied to predictable recurring revenue.
Vertical and scale considerations
Large enterprises (10,000+ endpoints) are the most at risk and the most lucrative. ControlUp’s dataset flags very large organizations as least likely to have completed migration, largely due to application complexity and geography. MSPs that can demonstrate multi‑region rollout experience and regulatory controls (data residency, audit trails) will win large deals.Specific vertical notes:
- Finance and healthcare: prioritize compliance validation, isolated test environments, and vendor sign-offs for regulated software.
- Education: high variance in device age — offer mixed strategies (Autopilot for new devices, ChromeOS/Cloud alternatives for legacy classrooms).
- Retail and manufacturing: peripheral compatibility and offline operation require device-by-device validation.
Employee experience as a commercial advantage
Treat migration as a product launch, not a maintenance task. Real-time DEX telemetry lets MSPs detect early signs of degraded user experience and address them proactively. Embedded user surveys and sentiment monitoring create measurable ROI stories you can present to procurement and business stakeholders: reduced helpdesk tickets, faster boot times, and improved application responsiveness. When MSPs can show quantified gains in user productivity and satisfaction, migration projects become strategic investments rather than cost lines.Risks MSPs must manage — and how to mitigate them
- Supply-chain and inventory delays: secure OEM or distributor commitments and build device-leasing options into proposals.
- Unclear scope and change orders: sell via phased pilots with clear acceptance criteria to avoid scope creep.
- ESU dependency: don’t position ESU as a long-term strategy; treat it as a last-resort bridge with clear expiry and migration deadlines.
- Reputational risk from failed upgrades: maintain image-based rollback plans and test automation; offer SLA-backed remediation windows.
- Sustainability backlash: offer trade-in and refurbishment pathways; document e‑waste disposal plans to align with client ESG goals.
Tech checklist for MSP delivery teams
- Ensure Intune/Autopilot connectors and ESP profiles are validated for each OEM and regional hardware variant.
- Validate firmware/UEFI updates and TPM provisioning before mass deployment; missing firmware fixes are a common post-upgrade failure mode.
- Maintain a catalogue of driver vendor contacts and sign driver testing with major ISVs for line-of-business apps.
- Instrument DEX before upgrades to create a measurable baseline for post-migration KPI reporting.
Measurable KPIs MSPs should report to customers
- Migration completion rate (by device cohort and business criticality).
- Post-migration incident volume and MTTR.
- End-user satisfaction delta (pre vs post upgrade) — use short in-app surveys.
- Cost savings vs. alternative options (ESU spend, emergency remediation).
- Environmental impact metrics where applicable (devices recycled, trade-in value recovered).
Strategic positioning: from migration vendor to digital workplace partner
The Windows 11 migration is a stepping stone to broader workplace modernization. MSPs should position migration as a gateway service that unlocks higher-value offerings:- DaaS and Cloud PC pilots (Windows 365) for remote and hybrid knowledge workers.
- Zero Trust and identity-centric security modernization.
- AI-enabled endpoint services as clients adopt Copilot+ PCs and on-device inference — sell outcomes (faster workflows, reduced meeting churn), not hardware alone.
Final assessment and recommended next steps for MSP leadership
The Windows 10 end-of-support deadline is a time-limited market with long-lived strategic upside. Short-term action matters because the window for low-friction upgrades is shrinking — but the correct response is measured, repeatable, and centered on employee experience.Recommended immediate actions:
- Launch a “Windows 10 EOL sprint” with a low-cost readiness assessment offer to current clients and prospects.
- Prioritize at-risk cohorts by business criticality and device eligibility; sell pilots to the highest-risk groups first.
- Bundle DEX monitoring into every migration to create measurable value and a natural upsell path.
- Build a commercial playbook that includes leasing and trade-in options to reduce refresh friction.
- Publicize success metrics quickly — case studies about reduced helpdesk volume and UX uplift will accelerate pipeline conversion.
Conclusion
Windows 10’s October 14, 2025 end-of-support is both a deadline and a door — a deadline that creates risk for organizations that delay, and a door to new recurring revenue and advisory relationships for MSPs that deliver migration outcomes with measurable employee experience improvements. The market is mature enough for partners to sell beyond the patch: the winning MSPs will combine readiness discovery, DEX-based execution, and aftercare optimization to turn a one-time migration into a strategic, multi-year managed services relationship.
Source: Managed Services Journal https://managedservicesjournal.com/...of-support-into-your-msps-next-growth-driver/