Software

It’s Never Too Soon to Start Planning for Windows 11 Deployment

Microsoft end-of-support for Windows 10 draws near. Here’s how to take the first steps to the next deployment.

Marty Spain is CDW•G's Director of Federal Services & Solutions, and leads a team of energetic problem solvers and creative thinkers to support some of the most complex national security systems.

Recently overheard among agency IT staff: “Windows 11? Didn’t we just finish deploying Windows 10?”

Yes, you did. And that puts your agency in an excellent position. The Windows 10 migration was all about making sure you had compatible hardware, and everything purchased or upgraded to handle that operating system is compatible with Windows 11. Now, you’re able to focus on preparing to take on Windows 11 and its cloud capabilities.

In addition, you’ve already had some practice in planning for Windows 11. The conversations that agencies have been having about creating zero-trust environments are similar to those you’ll have regarding Windows 11. In both cases, there’s a lot of planning, testing and validation of ideas before you start making the investment.

Technically, agencies have time before they need to make a hard push to Windows 11; Microsoft ends support for Windows 10 on Oct. 24, 2025, and will probably offer some extended support after that date, as it did for Windows 7.

But it never hurts to start planning early. Here’s where to begin.

Click the banner to find out more about Windows 11 support.

Software and Cloud Are the Primary Windows 11 Concerns

Again, hardware will not be the issue with Windows 11. In one way, this makes the transition easier: It will be less visible to the end user, who can continue to use existing equipment. IT administrators, however, will find the burden lies on them as they make changes to their day-to-day management practices.

For example, how does your ticketing system interface with how you manage devices, and what administrative processes change in that case? Users may have logged in to a particular device, but now they may be logging in to a cloud site.

Agencies will have to look at how they’re managing technology at the desktop level and decide if they’ll continue that method. If they’re using on-premises tools, will they stick with that, or will they migrate to some of Microsoft’s new administration tools?

This is a critical decision. Microsoft's ongoing strategy is to take advantage of Office 365 and Azure capabilities and move management and administration of Windows out of the data center and into the cloud. Will your agency follow? This is a question that must be asked before Windows 11 deployment.

2015

The year Windows 10 was released to the public

Source: Microsoft

Users Will Experience Less Disruption During Deployment

By the way, your agency isn’t the only entity that took lessons from the Windows 10 migration; Microsoft did too.

The company has rolled out plug-ins for its tools that should ease the process of identifying problems before the upgrade — and the tools are built into Microsoft’s enterprise management platform, which was not the case during the Windows 10 migration.

Once management decisions are made, the next step is to consider configuration. It’s common for enterprises to not reconfigure their operating systems after an upgrade. But Windows 11 comes with a slew of new capabilities — stronger security, in particular — and reconfiguration is a must.

This may be simpler than IT staff members expect. The Windows 10 deployment gave agencies a better handle on what was happening across their enterprise, and where dependencies lay between groups within their department or across the agency. There were cases where an upgrade for one department within an agency would have an adverse effect on another department that hadn’t upgraded yet.

But agencies now know where those dependencies are, and they have them mapped. Instead of the grueling path taken to install Windows 10, it’s possible that an entire agency could be upgraded at once, possibly over a single weekend.

Outside Help with Windows 11 Deployment Is Available

At this point, agencies have more than a year and a half before support for Windows 10 ends, but time moves quickly. Consider starting your Windows 11 planning in January 2024, and spend the first half of the year putting together a plan, identifying how the deployment will happen and in what order, and pinpointing your dependencies. You could have a robust plan in place by April.

In the spring and summer, start testing and try to get feedback before the end of the fiscal year in September. Think about being ready to test a proof of concept and limited deployment by October 2024; then, spend 2025 actually deploying the new operating system.

If you start now, you and your agency will have ample time to deal with any unforeseen issues. You will also have an advantage if you are working with industry partners or with Microsoft itself — as the Windows 11 deadline draws near, more enterprises will need assistance, and it may not be available in time for everyone.

When to call in assistance? If, during your preliminary testing and proof of concept, you’re not seeing the anticipated results, don’t waste time doing your own troubleshooting. Pull in industry partners or Microsoft immediately. Their broader experience with problems means that they can fix something in days that may take an inexperienced agency months — and again, the sooner you ask for help, the faster they’ll be able to get to you.

If agencies take the lessons learned from Windows 10 and bring those concepts forward, this should be a lot less painful. After all, Windows 12 may only be a few years away.

This article is part of FedTech’s CapITal blog series.