Orchestrating a Smooth Move to Windows 11

Fresno Unified School District’s Mindful Windows 11 Deployment

One district that has managed a very large deployment to Windows 11 is Fresno Unified School District. In February 2025, the California district began moving its fleet of 120,000 devices over to Windows 11.

“Microsoft made the announcement that they were going to end support for Windows 10, so we wanted to ensure that our district’s devices remained secure,” says Ricardo Aguilar, Fresno USD’s IT manager.

“One of the biggest challenges early on was determining the exact timing for moving forward with the deployment,” he continues. “We were mindful about minimizing classroom and instruction disruption. We wanted to avoid as many disruptions during the instructional time and testing periods as possible.”

Working Through Deployment Networking Issues

Fresno USD also faced a technical challenge: some transitioning devices wouldn’t connect to the district’s enterprise wireless network.

“We were relying on an enterprise wireless network when transitioning from on-premises Active Directory to Microsoft’s Entra ID in the cloud,” says Aguilar. “Those devices weren’t consistently connecting to our enterprise wireless network.” He explains that the district had to create a ticket and get Microsoft’s engineers involved to resolve the issue.

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Aguilar’s advice for districts that still have not moved over to Windows 11 is to include a communications plan with the deployment.

“We worked very closely with our ed tech team on a communications plan, including creating a Windows 11 tutorial page,” he says. “We began communicating early to our staff that Windows 11 was going to come out and put it on their radar. This helped smooth the rollout.”

Orange Unified School District’s Slow Roll to Windows 11

Staying up to date on security was a Windows 11 transition driver for California’s Orange Unified School District.

“We had a push to move people over to Windows 11 because of security,” says Orange USD CTO Tam Nguyen. “It was the biggest driving factor, getting more secure integration with Microsoft Intune, OneDrive and the Office Suite. And there was a push to move away from Windows 10 for better management and interoperability with Windows 11.”

Rather than making one big leap for all students and staff to Windows 11, the district has taken a gradual approach. It’s pushing out new Windows 11-compatible devices to 20% of its 23,000 users each year, beginning in 2021-2022, following the district’s typical refresh cycle.

LEARN MORE: Optimize K–12 devices for long-term success.

“Early on, we made sure all of our applications worked on Windows 11,” says Nguyen. “That was all the validation that we performed. The advantages of Windows 11 made it easy to adopt. Autopilot, Intune, OneDrive integration, single sign-on, integration into internet services with Microsoft Edge — the benefits to the end user were so great, we moved to it right away.”

The only technical hurdle for the staff was an older financial system that could not move to the cloud and had to stay on-premises, which was addressed with a hybrid Intune license. The rest of the district’s apps were moved to the cloud.

Early Adopters as Deployment Supporters

The biggest challenge for Orange USD has been staying on top of change management with staff.

“People don’t want to see change,” says Nguyen. “We make a point to communicate to staff that things are going to look different and that our technicians are available and ready to assist. For the first cohort, we sent out emails and also had our teams deliver the devices. We gave them a kind of white-glove service, then walked them through what was new.”

The gradual approach that the district took to transitioning to Windows 11 offers some upsides to districts still planning their move. “Once the first cohort was up and running, the next group was more open and less intimidated about moving over,” Nguyen says. “Winning over early adopters and then jumping to the next cohort increased the overall comfort with the changes.”

Communicating specific features to look forward to also helped with the deployment. “Early adopters talked about OneDrive working really well, that it integrated the single sign-on between their computer and websites or web applications,” notes Nguyen. “These were big selling points for those early adopters. Then, they told their friends. That helped us.”

Tools and Experts Help Check for Windows 11 Compatibility

For districts that are concerned about whether their devices are compatible with Windows 11 or not, Microsoft offers the PC Health Check app, which can be run on devices to see if they are compatible. The district’s IT solutions provider can also scale up the device compatibility scan for districts.

“CDW has a help service that comes in and does a complete compatibility check across your entire fleet and provides a report and roadmap,” says Brown. “Schools are told yes or no on devices, these applications are greenlit, and these applications are going to be a problem or need an update.”

FIND OUT: Do your devices meet the requirements for Windows 11?

Districts already using Intune have an even easier way to get compatibility reporting. “If you’re using Intune, you can pull hardware compatibility reports right there,” says Genis. “In fact, with Intune, you can push Windows 11 to that device. It will update automatically.”

“A lot of times, districts are scared to go fully to the cloud,” Genis adds. “They’ve been running on-premises, and getting rid of servers is a big change. Intune is that tool that can really integrate however you need it to work.”

She notes that there are options for school districts who are hesitant. “If you have Microsoft System Center Configuration Manager, Intune could run co-management. Now you’re hybrid. You don’t need to move to full cloud, but if you want to take that initiative, you can with Intune. It gives districts the flexibility to move toward Windows 11.”

“There’s a lot of help available, and there are so many things that Microsoft and solutions providers are doing hand in hand for education,” says Brown. “We all want to help districts grow their environment and make sure it’s optimized and properly set up in Windows 11.”