Microsoft will end support for Windows 10 on Oct. 14, 2025, and MSPs are urging clients to migrate to Windows 11 to avoid issues with security and obsolescence. Of course, it doesn’t hurt that a mass migration may significantly boost opportunities for MSPs to upsell services.
“MSPs have a huge opportunity here to showcase ongoing support and bring in clients that could turn into managed clients for the MSP,” says Esteban Blanco, chief geek officer at Blanco I.T., an MSP in Arlington, Texas. “Furthermore, there is an opportunity to sell new devices, as there will be a lot of machines that do not meet system requirements for Windows 11 or are out of support already.”
Indeed, last year Canalys estimated that 240 million PCs are incompatible with Windows 11. For Jeremy Colwell, founder of Vancouver, British Columbia-based The Human IT Company, “the Windows 11 migration is not so much an opportunity to upsell services as it is an opportunity to upsell hardware. What we are doing as part of these conversations is talking to our customers about other types of projects such as cloud file migrations. But that said, any time we have an opportunity to sit down with our customers in a nonsupport context there are sales that come as a result of that.”
Stuart Bryan, president of I-M Technology, an MSP in Norwich, Connecticut, also expects new opportunities from the OS migration. “The migration to Windows 11 should be an opportunity to discuss AI, cloud computing, and overall business strategy,” he notes.
The Security Imperative For Migration To Windows 11
MSPs are warning clients failure to migrate will produce two perilous outcomes: One, their PCs will be more vulnerable to cyberattacks because Microsoft will no longer issue Windows 10 updates and security patches. And two, as a result, MSPs are unlikely to support those PCs going forward.
Security is the main reason for migrating, and MSPs can capitalize on that by selling managed security services, says Blanco “Hackers want every bit of data out there, useful or not. So they are going to find those machines that are not in compliance with hardware.”
MSPs are telling clients about the need to migrate through one-one-discussions, emails, phone calls, blogs, and quarterly meetings. Among other initiatives, I-M Technology has run a postcard campaign about Windows 10 end of life and emailed every client a PC lifecycle report, says Bryan. He estimates that 25% of I-M Technology clients’ PCs are incompatible with Windows 11. Other MSPs put their estimates at anywhere from 10% to 30%.
Will Desire For AI-Enabled PCs Drive the OS Migration?
Microsoft is pushing AI capabilities as a primary reason to switch to Windows 11. But so far, MSPs interviewed for this article say AI isn’t much of a factor. Out of Blanco’s 125 clients, exactly one has expressed interest in it, he says.
Randell Bunn, director of technical services at Warren Averett Technology Group, an MSP headquartered in Birmingham, Alabama, says his company isn’t pushing AI-enabled machines. “With Copilot being an add-on option, it accomplishes the current needs of our clients. AI-enabled PCs are fairly new. While we like being on the cutting edge, we don’t prefer the bleeding-cutting edge.”
Bryan says AI-enabled PCs are not I-M Technology’s standard build, though he expects that will change in the first quarter of next year when the provider decides whether to change system configurations. “We generally establish baseline systems each quarter. The AI-enabled ones simply aren’t in the Q4 baseline configurations.”
Justin Faith, service manager at Automated Office Solutions, an IT consulting and manage service business in Evansville, Indiana, equates AI’s significance to the discovery of fire, but says it’s too early to tell how much it will impact SMBs.
“Microsoft’s Copilot is shaping up to be the leader in this space,” he says. “Companies that can integrate the new technology into their existing business model will without a doubt increase their capability in most every area. Businesses that are slow to adopt will find their competition more agile and aggressive as they begin to rely heavily on the technology.”
Overcoming Resistance to Change
Despite the potential benefits of migrating and the dangers of running PCs with an unsupported OS, some businesses resist switching to Windows 11 until they don’t have a choice. That usually happens when new releases of business applications stop running on the OS, says Faith.
“Typically, what we see being the biggest driver to adopt a new OS is when their line-of-business application development cycle ends support for Windows 10. That’s typically when the hold-outs move as the main program they use to run their company informs them they aren’t supporting the older operating system,” Faith says.
Blanco says fear and inconvenience also play a role. “A lot of times people are afraid of change. That’s just human nature,” he says. They also don’t like interface changes that move their icons around, so Blanco I.T. tries to minimize disruption. “We take a picture of the desktop and make it feel as close to Windows 10 as we can,” he says.
Bunn says his company hasn’t encountered customers resisting migration. “If we do, we will discuss the potential security risks and what mitigating controls would need to be put in place on the client’s network to protect them. Many times, updating the workstation will be simpler and more cost effective than implementing any mitigating controls.”
Why Migration To Windows 11 Is A Win/Win
October 2025 may seem far off, but MSPs warn about putting off migration. MSPs like Bryan and Blanco are talking to hardware vendors about ways to make migration affordable through lines of credit and group buys. While many MSPs don’t profit from hardware sales, they can still profit by upselling services, which makes migration a win/win for providers and clients.
Talking with prospects about end of support for Windows 10? Be sure to read Transform Your Sales Strategy With These Proven Discovery Meeting Tips
