With Windows 10 support ending in October 2025, it’s time to prioritise your upgrade strategy.

We spoke with our very own Rob Baird, Modern Workplace Architect here at Cyclone, to unpack answers to the 10 most common questions IT leaders are asking as they plan for a smooth migration.

 

1. Is our current hardware compatible with Windows 11?

“First step? Get a full inventory of your fleet,” says Rob. “You’ll want to know what’s being replaced, repurposed, or virtualised.”

Look at whether your devices meet core Windows 11 requirements, such as TPM 2.0, Secure Boot, compatible CPU, RAM and storage. Short-term workarounds may be possible for non-critical users but be realistic about total cost of ownership.

As organisations replace older hardware and look to modernise, being future proof and adaptable to whatever scenario your staff work in is critically important. “Having devices like the HP EliteBook X Flip means you are best placed for ensuring staff can remain mobile and secure with high performance kit,” says Rob.

“Ideally this isn’t thought of as just a tech upgrade. It’s a chance to rethink UX, hybrid work readiness and future support models.”

 

2. Are our critical business applications compatible with Windows 11, and tested?

Rob believes that most standard apps will run. “App compatibility between Windows 10 and 11 is cited by Microsoft as over 99% of apps,” Rob explains. “But the issue often lies with legacy software that hasn’t been validated by the external vendor for Windows 11.”

If an app hasn’t been certified or upgraded, it could mean unexpected costs, or even security risks. Cyclone can help identify and test high-risk applications early.

 

3.What’s the scope and timeline for the migration?

“Once you know which devices, users, and locations are involved, you can plan the rollout,” says Rob.

Break it into phases: pilot, non-critical users, critical systems. Lock in milestones and don’t forget post-launch support. Deployment is what you’re working towards, but managing any troubleshooting post-launch is also key.

 

4. What are the risks of staying on Windows 10 after support ends?

“There’s always risk, especially with compliance-heavy workflows,” says Rob. Unsupported software opens the door to security vulnerabilities, and that risk only grows over time.

The risk isn’t limited to just Windows, it’s also the apps you rely on today. After support ends, vendors will stop testing and validating on Windows 10 and move towards Windows 11 as their base.

“A successful Windows 11 migration is more than a refresh. It’s a chance to assess your compatibility, security posture, and user experience.”

 

5. How will we migrate user data and settings at scale?

“There’s no one-size-fits-all,” Rob says. “Every organisation has unique requirements, but data security and integrity must be top priority.”

Plan for secure backup and recovery and test your process before go-live. Have a robust rollback plan for edge cases. Cyclone supports organisations with tailored strategies for safe and seamless data transfer.

 

6. How will we handle user training and change management?

“Training needs are usually minimal; most people know their way around Windows 11 and have seen it before. But don’t underestimate the impact of small changes,” advises Rob.

That includes UX tweaks, like the repositioned Start menu. “A simple cheat sheet for support teams goes a long way. And in larger orgs, internal comms is helpful.”

Cyclone also offers info sessions and user onboarding, which Rob says have been well received in large-scale rollouts.

 

7. What’s the budget and resourcing requirement?

“You’ve got three buckets,” says Rob. “Hardware, software, and labour. Your biggest variable will be the hardware-related costs, especially if you’re replacing many older devices or don’t have a good grasp on what you need to replace.”

Also, budget for support and training, backfilling helpdesk staff during the change window so BAU can carry on and plan how you’ll demonstrate ROI to the C-suite.

 

8. What’s our plan for post-migration support?

“Too many organisations overlook this,” Rob warns. “You need to plan beyond launch day.”

Whether it’s additional helpdesk resources or monitoring tools, ensure you have capacity to manage performance, user feedback and troubleshooting.

“If your service desk is already stretched, this could tip it over. Pilot phases are crucial to understanding how you might be impacted in a wider rollout.”

 

9. How will we minimise disruption and maintain continuity?

Timing matters. “Avoid high-pressure business periods and run a good pilot first.”

Rob recommends upgrading a sample group first and closely tracking the results. Sometimes it can be the smaller things that emerge as the most common queries.

“For example, for one client, a simple pop-up message explaining perceived post-install slowness saved the support desk from being overwhelmed over this issue.”

 

10. Are we ready to update security policies and use new features?

Windows 11 offers many security features, but only if you activate them.

“Use this migration as a chance to review your licensing, tools, and configurations,” says Rob. “There’s probably functionality you’re already paying for — Intune, Security Baselines, Conditional Access — that just hasn’t been fully used.”

A common trend Rob sees is organisations shifting from SCCM/Config Manager to Intune to enable more modern, cloud-based management.

Don’t leave it too late.

“These are the questions IT leaders need to be asking now,” Rob says. “A Windows 11 migration isn’t just about compliance, it’s an opportunity to modernise.”

Whether you’re a CIO, CTO, or IT Manager, the clock is ticking and the decisions you make now will shape your organisation’s productivity, security, and budget for years to come.

Talk to Cyclone about how we can support your Windows 11 transition, from assessment and planning to rollout and beyond.