The Summer of Migrations

It was an incredible summer this year — possibly my busiest ever, and pleasingly, one of the most successful.

With the Windows 10 end-of-life deadline now appearing in the rear-view mirror, I thought it might be interesting to share the story of what it took to migrate 20 schools, 13,500 users, over 2,500 devices, and tens of terabytes of data away from on-premise Windows Server environments — and into the cloud.

Deciding a Strategy

We’ve known about Windows 10’s impending doom ever since Windows 11 was released. Microsoft has been transparent about end-of-life timelines, yet, at the start of this year, Windows 10 was still the dominant platform across our schools.

Sure, we had already moved many to the cloud — but with new schools joining and others still relying on legacy setups, there were plenty left to transition. The real challenge was convincing schools to move away from systems that “still work” — and often, with no budget.

First, we needed to understand what we were moving them to. We could have simply completed in-place upgrades, left servers on-prem, and rolled out basic Windows 11 policies. Honestly, that would have been more profitable — it takes more engineer time and less change management.

But it wasn’t the right thing to do.

Instead, we saw an opportunity to help schools save money, improve security, and simplify their IT. We made the decision that we would no longer support Windows Servers for device management, data storage, or user management. Everything was going cloud-first.

Putting Together a Plan

Once that strategic line was drawn, the next question was: how?

Every school is different — but similarities exist. We began with detailed internal and customer-led audits of systems and infrastructure. This wasn’t just about finding out what schools actually had, but also what they thought they had — and the two don’t always match!

Once we gathered the data, we scoped what needed to happen. We decided on a fixed-price migration model that covered data, devices, and users. This gave schools confidence and predictability, allowing them to budget effectively and know exactly what was included.

Communicating the Plan

Schools have a lot on their plate — and with the project running across the end of the spring term into summer, communication was everything.

We were fortunate to work with some forward-thinking schools and an amazing team of Customer Experience Managers (CXMs) who helped bridge the gap.

While the fixed price covered core migration elements, every site had unique needs — such as printing setups, MIS hosting, Paxton/Net2, cashless catering systems, and of course, licensing. Being transparent about what could and couldn’t be moved to the cloud made all the difference.

Delivering the Goods

No two migrations were alike. Some were straightforward moves from on-prem to an existing tenancy. Others involved cross-tenant migrations, consolidations into MAT tenants, or even Microsoft ↔ Google transitions. In a few cases, we migrated already cloud-based schools into new cloud environments — complete with Azure server transfers.

We used a combination of SPMT, ShareGate, and MigrationWiz to move data — covering everything from user home folders and shared drives to OneDrive, Google Drive, SharePoint, and Shared Drives.

For user creation, many schools adopted Automate (Salamander) to link their MIS to their chosen platform. For others, we used our custom PowerShell toolset to bulk-create users, auto-generate SPMT CSVs, and manage dynamic group membership and licensing.

Device readiness was another major focus. We audited fleets, identifying which could upgrade to Windows 11 or pivot to ChromeOS Flex. We then deployed version-controlled Intune and Google policy baselines, tailored with school-specific settings, and trained our engineers to master cloud-based software deployment.

Much of this work happened quietly behind the scenes — so by the time we arrived on site, the migrations were fast, focused, and minimally disruptive.

I actually prefer migrating in term-time: being on site means we can support users immediately, resolve quirks in real time, and build confidence with staff — rather than returning from summer holidays to an unfamiliar setup.

Meanwhile, our Helpdesk worked tirelessly to support users remotely, our onsite engineers tackled local issues, and our CXMs maintained strong communication throughout.

Aftercare and Training

 Training in action

Technical work is only half the story. Aftercare is what makes it stick.

For many schools, collaboration tools like SharePoint and OneDrive were brand new experiences. Others were switching platforms entirely. Providing training and follow-up sessions was key — and seeing staff confidently embrace cloud tools was genuinely rewarding.

It wasn’t just about showing how things worked — it was about demonstrating why the change mattered: security, efficiency, accessibility, and long-term sustainability.

Will It Ever Happen Again?

Probably not on this scale.

Some schools are still on-prem, but now that devices are managed through Intune or Google, updates and configurations can be deployed centrally and securely. The days of physical server migrations may be fading — and that’s a good thing.

But while we may not have another “Summer of Migration” quite like this one, there will always be new challenges, technologies, and opportunities ahead.

And I, for one, can’t wait to see what comes next.