Key Takeaway: Windows 10 reached end of support on October 14, 2025. The conversation is no longer about whether to upgrade. It is about how to manage the risk of devices that have not been upgraded yet. The most urgent reason to address Windows 10 devices is not the security risk itself. It is the cyber insurance implication.
Windows 10 reached end of support on October 14, 2025. Microsoft confirmed this date years in advance, and yet a significant portion of the business PCs in most MSP client portfolios are still running it. The reasons are familiar: budget constraints, hardware that cannot run Windows 11, line-of-business applications that have not been tested on the new OS, and the general human tendency to defer decisions that feel expensive and disruptive.
The end of support date has passed. The conversation is no longer about whether to upgrade. It is about how to manage the risk of the devices that have not been upgraded yet, and how to have the client conversation that gets the remaining devices addressed.
What End of Support Actually Means
End of support means Microsoft will no longer provide security updates, bug fixes, or technical support for Windows 10. The operating system will continue to function. Devices running Windows 10 will not suddenly stop working. But every vulnerability discovered after October 14, 2025 will remain unpatched on those devices indefinitely.
According to Microsoft’s official lifecycle announcement, this applies to Windows 10 Home, Pro, Enterprise, and Education editions. The only exception is the Extended Security Update (ESU) program, which provides security updates for Windows 10 through October 12, 2027, at a cost that increases each year.
The practical implication for MSP clients: every Windows 10 device in their environment is now running an operating system that will accumulate unpatched vulnerabilities over time. The longer those devices remain on Windows 10, the more exposed they become.
The Cyber Insurance Problem
The most urgent reason to address Windows 10 devices is not the security risk itself. It is the cyber insurance implication.
Cyber insurance carriers are increasingly asking about end-of-life operating systems on their applications. A client who has Windows 10 devices in their environment and does not disclose them on the application is misrepresenting their security posture. A client who discloses them may face premium surcharges, coverage exclusions for incidents involving those devices, or outright denial.
The MSP that helps clients understand this connection is delivering genuine advisory value. The conversation is not “you need to upgrade because Microsoft says so.” It is “your cyber insurance renewal is coming up, and your carrier is going to ask about end-of-life operating systems. Here is what that means for your coverage and what we need to do about it.”
The Hardware Problem
Windows 11 has specific hardware requirements that many older devices do not meet. The minimum requirements include a 64-bit processor running at 1 GHz or faster with at least 2 cores, 4 GB of RAM, 64 GB of storage, UEFI firmware with Secure Boot capability, and TPM version 2.0. The TPM 2.0 requirement is the most common barrier: many devices manufactured before 2018 do not have TPM 2.0.
The RAM shortage of 2025 and 2026 has made hardware replacement more expensive than it was when Windows 11 launched. A device that would have cost $600 to replace in 2023 may cost $800 to $1,000 in 2026. This is a real budget impact that clients need to plan for, and it is a conversation that should have started before the end of support date, not after.
For devices that cannot run Windows 11 and cannot be replaced immediately, the Extended Security Update program provides a bridge. The ESU program costs $61 per device for the first year (2025-2026), $122 per device for the second year (2026-2027), and is not available for a third year. It is a temporary solution, not a permanent one.
The Client Conversation
The clients who are most resistant to the Windows 10 upgrade conversation are usually the ones who are most exposed. They have deferred the decision because it feels expensive and disruptive. The MSP’s job is to make the cost of inaction visible.
The conversation that works: we have identified [number] devices in your environment that are running Windows 10, which reached end of support in October 2025. These devices are no longer receiving security updates, which means every new vulnerability discovered will remain unpatched on those devices. Your cyber insurance carrier is going to ask about this at your next renewal. We need to address it before then. Here is what that looks like and what it costs.
The conversation that does not work: you need to upgrade because Microsoft says so. That framing makes the upgrade feel like a vendor requirement rather than a business risk. The client who understands the cyber insurance implication and the security exposure will make a different decision than the one who hears “Microsoft wants you to buy new computers.”
The Upgrade Path
For devices that meet Windows 11 hardware requirements, the upgrade is free and can be deployed through your RMM. The process is straightforward: verify hardware compatibility, back up the device, deploy the upgrade, verify the upgrade completed successfully, and document the new OS version in your asset inventory.
For devices that do not meet Windows 11 requirements, the options are:
Replace the device. The right answer for devices that are more than four years old or that are approaching the end of their useful life anyway. The replacement cost is a one-time expense. The ongoing security risk of keeping an unsupported device is a recurring liability.
Enroll in the ESU program. The right answer for devices that cannot be replaced immediately due to budget constraints or line-of-business application dependencies. The ESU program provides security updates through October 2027. It is a bridge, not a destination.
Isolate the device. For devices that run specialized software that cannot be migrated to Windows 11, network isolation reduces the risk of a compromised device affecting the rest of the environment. This is a risk mitigation measure, not a solution. The device should still be replaced as soon as the application dependency is resolved.
Frequently Asked Questions
Will Windows 10 devices stop working after end of support?
No. Windows 10 devices will continue to function after October 14, 2025. They will not receive security updates, bug fixes, or technical support from Microsoft, but the operating system will continue to run. The risk is not that the device stops working. The risk is that it accumulates unpatched vulnerabilities over time.
What is the Windows 10 Extended Security Update program?
The ESU program provides security updates for Windows 10 through October 12, 2027, at a cost of $61 per device for the first year and $122 per device for the second year. It is available through Microsoft and through volume licensing channels. It is a temporary bridge for organizations that cannot complete their Windows 11 migration before the end of support date.
How do I identify Windows 10 devices in my clients’ environments?
Your RMM should be able to generate a report of all devices by operating system version. Run this report for every client and document the results. The report is also the evidence you will need for the cyber insurance application.
About Brent Lacy: Brent Lacy is a technology advisor and the voice behind Rewired MSP. He helps MSPs operate with greater maturity and helps business owners make IT choices that make them more secure and more efficient. He is the author of Rewired MSP: Mastery, Scalability & Performance, vCIO Rewired: Virtually Conquering IT Obstacles, and Near Miss: Preventable IT Failures Threatening Your Business Security.
Related Reading
- Microsoft Deleted Its 32GB RAM Advice: What Clients Should Actually Buy
- Cyber Insurance Requirements 2026: What Carriers Actually Check
- MSP Cybersecurity Hub
- vCIO Services Hub
- Building a Technology Roadmap: The vCIO’s Most Powerful Tool
