Nov 22 2023

How State and Local Agencies Can Transition to Windows 11

A CDW Readiness Assessment works to help organizations migrate while maximizing effectiveness and minimizing risk.

Windows 11, the newest iteration of Microsoft’s operating system, is ready for deployment by organizations. But is your organization ready for Windows 11? The end of life for Windows 10 — Oct. 14, 2025 — will be here soon enough, and Windows 11 comes with new software and hardware requirements along with important changes to its user interface. The time to prepare for a transition to Windows 11 is now.

To get ready, organizations must assess their environments and create effective migration plans. But the reality is that state and local agencies are always up against limited resources for technological upgrades, which means that agencies ready to make the jump may need help.

I’m a CDW•G software solutions executive who works in government Microsoft licensing, and we can help make sure that the systems our government customers are running are compatible with the new OS. Here’s what we do at CDW to help agencies get their environments ready for Windows 11.

LEARN MORE: Follow expert guidance to manage your Windows 11 migration seamlessly.

Conducting a Readiness Assessment for Windows 11

State and local governments would do well to start assessing their Windows 11 compatibility now. In my years in the government space, I’ve seen instances in which organizations try to upgrade and fail because they have applications running on old OSs. Plus, agencies need to know whether their vendors and original equipment manufacturers will work with Windows 11, and if not, get a timeline for when they’ll be compatible. A readiness assessment uncovers these potential roadblocks.

There are multiple phases to the Windows 11 CDW Readiness Assessment. In the first phase, our experts run tools in an organization’s existing environment to analyze current on-premises device management solutions and security features and conduct hardware and software analyses to determine compatibility and reduce any migration risks.

CDW’s assessment also helps organizations get a closer look at the features of Windows 11, understand the different editions of the OS, develop deployment methods, create a managed application list for future support and develop a roadmap for an enterprisewide Windows 11 deployment.

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Envisioning a Windows 11 Future

After the assessment comes the envisioning phase, in which CDW works to understand how an organization operates today and how Windows 11 fits into its workflows. CDW helps agencies determine this through an envisioning workshop with key administrators and project stakeholders, who make sure that moving to the Windows 11 OS will meet all of the necessary requirements within the environment.

Will migration require new hardware or just a software update? Can we stick with our current vendors or will we need to change? The envisioning phase answers these questions. The next phase of the readiness assessment involves planning and design, where CDW works with agencies to discuss user enablement training, communication and support requirements to ensure a smooth migration. End-user enablement is key to migration so that organization staff will understand what they’re working with as they encounter changes made to the Windows user interface, significantly reducing support requests.

DISCOVER: Questions your organization should ask itself before Windows 11 adoption.

Streamline Migration with Windows Autopilot

Next comes the pilot deployment, in which Windows 11 is rolled out to a small group of users at an organization to test the migration plan created in the envisioning phase. Depending on the size of the organization and the nature of the migration plan (such as whether it requires new hardware), the pilot phase could take a bit of time.

In a hybrid work environment, it becomes even more difficult to swap out hardware and get all users on the same page, which is where Windows Autopilot comes in handy. With Autopilot, all end users need to do is connect to a network and use their company credentials to log in; updates, settings and applications are downloaded automatically to their machines.

READ MORE: Manage legacy systems with strategic application modernization assessments.

When devices are purchased with Windows Autopilot through CDW, we can help organizations through the process. First, CDW registers an organization’s new devices and enrolls them into the organization’s mobile device management solution before shipping them. Once shipped, users sign in and start the automated configuration. Devices are then ready for use.

Autopilot can also be used to upgrade existing devices from Windows 10 to 11 through a user-driven mode using a single Configuration Manager sequence. From there, Microsoft handles ongoing device patching through Windows Autopatch.

This article is part of StateTech’s CITizen blog series. Please join the discussion on Twitter by using the #StateLocalIT hashtag.


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