Windows 11 migrations: the real blockers in enterprise
Windows 10 support ends in October 2025. Enterprise migrations to Windows 11 are progressing, but more slowly than Microsoft would like. Here's why.
October 14th, 2025 is the end of extended support for Windows 10. That's not far away, and the enterprise world is not as far through its Windows 11 migration as it should be.
I've been part of several Windows 11 migration projects over the past year and a half. Here's why the migrations are slower than they should be and what the actual blockers are.
The hardware compatibility problem is real
Windows 11's hardware requirements are the most well-publicised obstacle and they're genuine. TPM 2.0, Secure Boot, an 8th-generation or newer Intel CPU (or AMD Zen 2 or newer, or Qualcomm). Older hardware fails the compatibility check and cannot upgrade.
The scale of the hardware compatibility problem varies enormously by organisation. I've worked with customers where 80% of their estate is compatible; I've worked with others where it's 40%. The incompatible machines require hardware refresh; they cannot be in-place upgraded.
Hardware refresh at scale takes time and budget. For organisations that haven't started, two years sounds comfortable. When you factor in procurement lead times, deployment capacity, user scheduling, and the inevitable delays, it's tight.
Application compatibility is the hidden problem
This is the one most organisations underestimate. Windows 11's application compatibility is actually very good. Microsoft has put significant effort into ensuring backward compatibility. The vast majority of applications that run on Windows 10 will run on Windows 11.
The problem is the applications that don't, and you often can't identify them without testing. That 15-year-old line-of-business application that runs on .NET 3.5 with a dependency on a 32-bit COM object? Nobody's tested it on Windows 11 yet. The specialist industry application your finance team has been running since 2014? The vendor may have a Windows 11 compatible version, or they may not.
Application compatibility testing is unglamorous work. It requires someone to identify every application in use across the estate, find the owner, test it on Windows 11, document the result, and plan the remediation for anything that fails. For a 500-user organisation with 200 distinct applications, that's a significant project in itself.
The co-management dependency
If you're still primarily SCCM-managed and haven't completed the Intune co-management transition, your Windows 11 migration path is more complex. Windows 11 is deployable via SCCM, but the modern Windows 11 device management story (Autopilot provisioning, cloud-joined, Intune-managed) requires having the Intune infrastructure in place.
Some organisations are trying to run the Windows 11 migration and the Intune migration simultaneously. This is technically possible but project-risk-heavy. Better to have the modern management infrastructure solid before tackling a Windows 11 rollout at scale.
What actually works
The migrations I've seen proceed smoothly have a few things in common:
A hardware inventory baseline done early. Know exactly what hardware you have, what's compatible, and what needs replacing, before you start planning the project timeline.
Application testing as a project workstream, not an afterthought. Dedicated resource, clear methodology, documented results.
Pilot group that's representative of the problem. Don't pilot with the IT team and call it done. Pick a group that represents the breadth of applications and working patterns in the organisation.
Clear communication to users. Windows 11 looks different enough that user preparation matters. A proper change communication plan prevents unnecessary support calls.
October 2025 is achievable if you start properly now. It's not achievable if you're waiting for it to feel urgent.
