For all Windows 10 users, the October 14 deadline marking the end of Microsoft’s support for the popular computer operating system is just about here.
Business users have known this deadline was imminent since April 2023, when Microsoft announced its planned transition to
Windows 11 and its resulting end of support and critical maintenance and security patches for the expiring operating system.
So, are businesses ready for the end of Windows 10 support and the move to Windows 11?
Well, not quite, according to a sampling of MSPs and consultants that recently spoke with ChannelE2E about how their clients have been preparing for the resulting changes in their IT operations and user experiences.
“Every MSP still has Windows 10 holdouts; it is inevitable,” said
Michael Slater, head of sales for Microsoft and cybersecurity at
Sherweb, a Quebec, Canada-based cloud marketplace and IT services distributor for MSPs. “The real task is not panic-upgrading but to help partners decide where to modernize now and where to mitigate risk temporarily. Our role is making sure those conversations stay about business outcomes, not just OS deadlines.”
From business customers to MSPs and other channel partners helping in the Windows 10 to 11 transition, the crucial issues are whether their existing older PCs and laptops are upgradeable to Windows 11 or if they need to be replaced with new machines that are powerful enough to run the new OS. Windows 11 has more stringent hardware security requirements that prevent it from being used on many machines that are only three or four years old.
“Some hardware makes the jump, and some does not,” said Slater. “There is always a scramble when deadlines get real. But a lot of partners do not treat this as just another upgrade. They turn it into an opportunity to simplify environments, strengthen security, and open the door to broader managed services conversations.”
Some customers have even moved to using Microsoft Azure Virtual Desktop (AVD), an option that lets them use Microsoft 365 licensing benefits to get around limitations of their old hardware, he said.
“The best outcomes happen when partners shift the discussion from compliance to modernization,” said Slater. “Whether it is upgrading, refreshing, or bridging, the opportunity is to attach services, improve customer experience, and position the partner as a long-term advisor, not just a license reseller.”
In recent months, Microsoft has offered several scenarios for customers to receive special paid or free Extended Security Updates (ESU) for up to a year to give customers more time to move to Windows 11.
“Some are [doing that], and some will keep delaying as long as possible to support legacy apps, just like in past transitions,” said Slater. “But it is the same stopgap it has always been. It buys time, but Microsoft will eventually close the door. Our message to partners is simple: short-term patches do not solve long-term problems.”
More Disruptive than the Windows XP Transition
Colin Knox, the CEO of Alberta, Canada-based
Gradient MSP, told ChannelE2E that he sees this transition from Windows 10 as even more disruptive for businesses than the one that came back in 2009 when Microsoft ended its official support and patches for Windows XP.
“This moment with Windows 10 feels like déjà vu, only at a much larger scale,” he said. “Back then, we were dealing with a relatively small number of outdated machines that could limp along a little longer. Now, Windows 10 is still the dominant OS in SMB environments, and the October 14 deadline creates a much bigger pressure point.”
While some MSPs have customers who acted early on Windows 10 decisions, many are still dragging their feet,” said Knox.
“Just like with XP, there is always a portion of customers who do not take action until the very last minute, and that is when MSPs end up firefighting,” he said. “The reality is that hardware refresh cycles were not perfectly aligned with this deadline, so there is a scramble now to either stretch existing investments or bite the bullet and upgrade.”
Knox said that some users see Microsoft’s ESU program as a short-term band-aid, but added that “most MSPs I have spoken with are advising against relying on this unless absolutely necessary.”
All these experiences for customers should be remembered as lessons learned for the future, he said.
“As with XP, many SMBs underestimated the lead time required” for deciding what to do about the arrival of the new Windows 11 OS and how it would affect their operations, said Knox. “The more proactive ones are fine now, but plenty are scrambling.”
“For MSPs, this is another reminder of why lifecycle management and forward planning are critical,” he said. “If customers see this only as a Microsoft problem, they will always be reactive. If MSPs frame it as part of an ongoing modernization journey which improves security posture, productivity, and cloud-readiness, then the conversation shifts from fire drill to strategic investment.”
At
NextTech Consultants, an IT services company in Newberg, Oregon, owner
Josiah Philipsen told ChannelE2E that right up until the deadline, he is still helping some customers with system upgrades.
“For the most part, clients have been willing to upgrade their computers,” he said. “The hardest computers to upgrade are the ones with special software on them, and the software company has not rolled out Windows 11 support yet. The process has been a bit time-consuming, but not a hard process to get people upgraded.”
Some customers who use specialized applications might be interested in the ESU option, and he is working with them to resolve those cases, he said.
“Most customers understood that moving forward earlier would help with the pressure of the upgrade, but we have a few clients who put it off because they did not want to put the expense up now,” said Philipsen. “We are working on plans for them and letting them know they must upgrade or in some cases we may have to take the computer off the network if they need to meet PCI or HIPAA compliance requirements.”
Some MSP Advice for Microsoft on Future Windows Transitions
At New York City-based MSP
Solarus Technologies Inc., CEO and co-founder
Matthew Nikravesh said that his company is deploying additional security software for customers who cannot afford hardware upgrades now to help protect them until they can
move to Windows 11. Some customers are also choosing to move to virtual desktops or lease computers to reduce expenses, he added.
“The clients who did not take action early enough stalled the process due to budgetary reasons or fear of tariffs and inflated costs,” said Nikravesh.
And for future operating system transitions, Nikravesh has some intriguing advice for Microsoft.
“In the future, I would love to see Microsoft offer the ESUs for 12 months as part of the Microsoft 365 suite, specifically Business Premium or higher,” he said. “This would provide MSPs with a viable alternative to extend support for a period of 12 months at no additional cost. This would generate a lot of goodwill for both us and Microsoft.”
Nonprofits Affected in Different Ways
Peter Fidler, the president and co-founder of
WCA Technologies, a New York City-based MSP, said that 25 of his business clients are nonprofits, which often put these Windows 10 decisions on the back burner due to other priorities.
“We will be working with them past the deadline,” he said. “Some are truly committed to the plan [to replace or upgrade computers]. Others are not as committed because of other funding needs. I really feel for these nonprofits that do not have the funding to replace these older computers,” due to government cutbacks.
An MSP Consultant’s Observations
Shawn Freeman, the founder of Alberta, Canada-based consultancy
Impactful MSP, said that MSPs tell him that they are doing whatever is needed to guide customers through the Windows 10 disruptions.
“Most MSPs that I'm working with still have a handful of customers who are not fully ready for the Windows 10 end-of-support deadline,” said Freeman. "These tend to be clients with older hardware, specialized software, or budget hesitations that caused delays. But overall, the majority have made meaningful progress, and this is not the widespread scramble we saw with past transitions like Windows 7.”
Successful MSPs started their client refresh planning 12 to 18 months ago, building hardware lifecycle management into their quarterly business reviews, said Freeman.
“They are aligning with customers on a predictable 4- to 5-year refresh cycle so these transitions become routine rather than reactive” in the future, he said. What is interesting is that MSPs are using more creative procurement models, including leasing, device-as-a-service, or monthly hardware bundles to help clients manage costs and avoid this kind of crunch in the future.”
“Larger and more mature organizations, or those working closely with a proactive MSP, are in good shape. But small businesses without strong IT planning often waited too long. Some are now rushing to replace machines or paying a premium for rushed deployments. The difference really comes down to how well the MSP had lifecycle and risk conversations earlier in the year.”
For MSPs, it is a lot of work getting these Windows 10 to Windows 11 transitions accomplished for customers, from coordinating supply chains to scheduling deployments and managing user expectations all at once, said Freeman.
“This deadline is highlighting a broader maturity gap in the SMB space,” he said. “The best MSPs have evolved from being reactive IT providers to strategic partners who guide clients through long-term planning and modernization. The MSPs that built refresh cycles, budgeting, and lifecycle management into their standard process are thriving. Those that did not are finding this transition painful for themselves and their clients.”
‘There Will Always Be Customers Who Resist the Upgrades,’ Says Analyst
All these Windows 10 transition scenarios are no surprise to
Jessica C. Davis, an MSP and MSSP analyst with Omdia.
“Omdia’s channel analysis shows that the worldwide PC market grew by 8% in Q2 2025 with 68 million units shipped,” she said. “Part of that strength comes from the Windows 10 end-of-service deadline refresh.”
But even while PC sales are up partly because of the Windows 10 transition, “there will always be customers who resist the upgrades, and times are tougher in 2025,” said Davis.
“Every unsupported Windows 10 endpoint after October 14 represents a potential liability for both the end customer and their MSP,” she said. “The risk of a cybersecurity breach is real, and when breaches occur, customers often blame their MSPs. The result can be customer churn or even litigation.”
MSPs must be wary and responsive in connection with these pressures, she said. “Even without an incident, MSPs that continue supporting non-compliant systems face margin erosion and operational drag. The most mature providers are assessing whether the cost and risk of maintaining obsolete systems outweigh the short-term revenue those clients bring.”
