MSP Execs Expect Windows 11 Migrations To Continue Long After Tuesday Support End Date
‘Our biggest competitor in this industry sometimes is apathy,’ says Jason Dugger, chief technology officer and co-founder of DGR Systems.
Tuesday marks Microsoft’s end of support date for Windows 10, but with analysts and solution providers telling CRN that the share of businesses that have moved to Windows 11 is around 70 percent, work will continue even into next year moving customers over to the new operating system.
Most customers who haven’t moved to Win11 are paying for extended security updates to stay on Win10, with some customers needing more time to test application performance in Win11 and more time to order new devices that will come running Win11.
Jason Dugger, chief technology officer and co-founder of Tampa, Fla.-based solution provider DGR Systems, told CRN in an interview that the passing of Tuesday’s Win10 support end date might actually make things easier for his employees to talk to customers that haven’t yet migrated to Win11.
Dugger, like other solution providers who spoke with CRN, said that ironically the ease of migrating from Win10 to Win11 may have inspired users to wait closer to the support end date.
Some customers also have a perception that Win11 is more of a version update from Win10 as opposed to an OS with major new feature upgrades, causing less urgency to move.
“It’s just not a priority for them,” Dugger said. “The general mindset is that it’s not that big of a deal. … Our biggest competitor in this industry sometimes is apathy.”
Windows 10 End Of Support
Mark Linton, Microsoft’s vice president for device partner sales, told CRN in an email that the vendor does not publicly share specific adoption or ESU purchase volumes, but it continues “to see strong engagement across customer segments.”
“Many organizations are actively planning their transitions ahead of the Windows 10 end-of-support deadline, and we’re focused on supporting them with tools and guidance to meet their timelines,” Linton said.
Microsoft partners have been “critical in working with customers for all aspects of migration planning,” he said. “We’ve seen strong engagement from across the ecosystem in helping customers plan and execute migrations or manage ESUs.”
Win11 has a 99.7 percent compatibility with Win10 applications, he said. Users can leverage Microsoft’s App Assure for application compatibility, Windows Autopilot and Intune for device management and Windows 11 Security Book and the Forrester EOS calculator to plan and build a business case for upgrading and minimize disruption.
IT teams can use the same tools and processes they already rely on for the Win11 migration, he said. And after Tuesday, Windows 10 PCs will no longer receive Microsoft Security Updates or system updates that provide protection against vulnerabilities or system updates that include defense-in-depth innovations that help protect against security threats.
He did point out that along with Win11, customers can opt to migrate to a cloud-based offer such as Windows 365 for security, modern productivity features and future-proofed IT environment
Asked by CRN about purchasing activity for AI PCs and Copilot+ PCs, Linton said that “Microsoft is thrilled with the momentum we’re seeing for Copilot+ PCs.”
“Customers and businesses are excited by the introduction of this new class of PCs, extending the power of AI from the cloud to your PC, and unlocking new Copilot+ PC experiences powered locally by the” neural-processing unit (NPU), he said.
The Redmond, Wash.-based vendor has about 500,000 partners worldwide. Top channel goals for 2025 include increasing the overall percentage of company revenue that comes through the channel and improving partner profitability, according to CRN’s 2025 Channel Chiefs.
Millions Of Devices Still On Win10
Mike Crosby, an executive director and industry analyst with Chicago-based research firm Circana, told CRN in an interview that based on his research, millions of devices are still running Windows 10 and will be vulnerable to cyber threats, compliance risks and operational disruption.
He estimates that two-thirds of health care sector devices and more than half of finance sector endpoints are on Win10, with issues including legacy software dependencies that need more testing on Win11 and hardware compatibility issues. Small businesses also tend to stick with devices much longer than large enterprises.
“This has been one of the slowest” Windows migrations he’s seen, Crosby said.
He estimates $7 billion in global ESU spending for the first year. In the lead-up to the Win10 support end date and as ESU anniversary dates come up, solution providers have opportunities to offer customers device readiness auditing and system auditing to find the highest risks and what needs to move to Win11 soonest, he said. Solution providers need to check their contracts to make sure they don’t hold any responsibility and liability around outdated and out-of-compliance devices.
Although Win10 ESUs continue security updates for PCs enrolled in the program, they don’t come with new features, customer-requested non-security updates, design change requests or general support for Windows versions past the end of support date.
The Win10 ESU only includes support for the license activation, installation and possible regressions of the ESU itself, according to Microsoft.
“The ESU, even at its best case, is a Band-Aid,” Crosby said. “They’re going to need a full functioning OS.”
Marcel Calef, Americas field chief technology officer for San Francisco-based digital employee experience (DEX) vendor ControlUp, told CRN that the vendor has seen a huge jump in the share of enterprise endpoints migrated to Windows 11 from the second quarter of 2025 to the third quarter, going from about 50 percent to about 80 percent.
Calef has seen a lag in the virtual desktop integration (VDI) space, with Win11 only accounting for a 40 percent share, up from 25 percent in June. Those migrations are more complex, he said. “There the curve hasn’t moved,” he said.
Research firm Statcounter Global Stats showed that in the U.S., Win11’s market share finally overtook Win10 starting in March 2025 and has been increasing share overall since, landing at about 61 percent share in September. That same month, Windows 10 accounted for about 35 percent of the market. Windows 7 still held about 2 percent share, where it’s been for at least 12 months, according to StatCounter.
Some Customers Play Chicken
Jasen Meece, president of Mesa, Ariz.-based Clutch Solutions–No. 259 on CRN’s 2025 Solution Provider 500, told CRN that his company has seen a flurry of activity over the past three weeks from customers who were hopeful for a delay to the support end date or ESUs becoming free.
“Some clients were trying to play the game to see if it (the deadline) would get kicked out,” he said. “They’ve since realized it’s not.”
The majority of his client base has migrated to Win11, and he estimated that about 50 percent bought new devices instead of just upgrading devices bought during the pandemic. Customers who went with ESUs to keep using Win10 are waiting for the next budget cycle to start in 2026 so that they can buy new devices.
Once a customer is clear of the Win10 or Win11 decision, Clutch can start talking to them about meatier subjects, including application modernization, public cloud adoption and whether AI workloads make more sense at the endpoint compared to the cloud, Meece said.
“This is going to be the beginning point of another one- to three-year tail on–now that you have the infrastructure, the hardware, the tools that can do it, what can you do with it?” he said. “People are not going to start training LLMs (large-language models), but they’re going to start to apply it to the stuff they have.”
Todd Pekats, vice president and general manager of software and subscription solutions at Fort Mill, S.C.-based CompuCom–a member of CRN’s 2025 MSP 500–told CRN in an interview that in the lead up to the deadline customers have sought ways to get free extended security updates, even leveraging their Enterprise Agreements (EAs) for ESUs.
He estimated that roughly 70 percent of Windows users are on 11, with many customers still on Win10 only staying for a few months. Some businesses can’t miss any workdays for even the simplest Windows migration, he said. “I totally get it when my customer says, ‘I can’t afford any downtime,’” Pekats said.
Customers understand the security risks with older OSes and want to keep their attack surface area to a minimum, he said. CompuCom has kept customers updated on risks and audits in quarterly and even monthly business reviews–some customers even have CompuCom employees on site for daily scrums.
Threat actors will look to exploit unsupported Win10 environments for at least a year or two after Tuesday, he said.
“There’s been a hesitation to buy the extended support SKU (stock-keeping unit) until you felt like you had no choice,” Pekats said. “Many customers have played chicken because it’s paid off for them.”
For customers sticking with an older OS, CompuCom has leveraged virtualization tools to isolate environments and provide more protection, but those efforts are usually temporary and have a cost.
“There’s no easy answer,” he said. “The only answer is, let’s really understand and qualify and quantify everything that you have”
Win10 Vs. Win11
Compared to Win10, Win11 adds features including smart recommendations in the Start menu and File explorer, Windows Studio Effects to eliminate distracting sights and sounds on video calls and instant live captions during Teams calls.
On the security side, Win11 adds passkey access instead of passwords for websites and apps and a smart app control that only permits reputable apps for installation. Win11 requires devices to have Trusted Platform Module (TPM) 2.0 for improved security and privacy.
Microsoft’s Linton called Windows 11 “the most secure version of Windows ever” with default protections and security features that aim to significantly reduce potential attack surfaces.
The solution providers told CRN that they are not aware of any customers running Win10 without extended security units, which they would advise against due to vulnerability to cyberattacks and the potential of coverage denial by insurance companies, who usually require businesses to conduct best practices and have the latest versions of software.
They also expect to continue migrating users to Win11 long after Tuesday’s Win10 deadline passes. DGR’s Dugger told CRN that he is still working with customers on Windows 11 readiness, assessments, piloting and provisioning for when they are ready.
Customers didn’t balk at the $61 per device cost of one year of Win10 extended security updates, Dugger said, especially compared to the cost of business downtime to achieve the Win11 migration.
But the price doubling each subsequent subscription year should help motivate DGR customers who haven’t yet moved to Win11. Windows 10 users can only buy ESUs for up to three years.
“We only get so much mind share, too, and these guys have long lists of things they need to get done,” Dugger said.
ESUs are available at no additional cost for Windows 10 virtual machines in Windows 365, Azure Virtual Desktop, Azure virtual machines, Azure Dedicated Host, Azure VMware Solution–including Citrix and Omnissa Horizon on Azure VMware Solution–Nutanix Cloud Clusters on Azure Azure Local (the former Azure Stack HCI), Azure Stack Hub and Azure Stack Edge, according to Microsoft.
The first version of Windows 10 released in 2015 with that version’s earliest end of support date in 2017. The latest version of Windows 10, 22H2, released in 2022, is the one losing support on Tuesday.
A variety of Win10 versions will continue to have support, including versions of Windows 10 21H2 IoT Enterprise purchased through the Long-Term Servicing Channel (LTSC), which is supported until 2032, according to Microsoft.
Microsoft released the first version of Windows 11 in 2021 and ended support in 2023. Older versions of Win11 including 23H2 and 24H2 continue to be supported. The latest version, released Sept. 30, is 25H2.