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3 ways to prepare for the Windows 7 deadline

Organizations holding onto Windows 7 for dear life should reconsider because Microsoft stops supporting the OS in January. Here's how to make the transition to Windows 10 smoother.

Microsoft is ending support for Windows 7, so laggards should ensure that their migrations to Windows 10 are well under way.

Windows 7 desktops won't simply stop working on Microsoft's Windows 7 deadline of Jan. 14, 2020. Still, Microsoft will no longer roll out software updates or technical assistance to those desktops, which makes management a challenge.

For organizations that are particularly stubborn, Microsoft offers the ability to virtualize Windows 7 desktops with Windows Virtual Desktop and host apps and desktops in the Azure cloud. Those organizations also have the option to purchase Windows 7 Extended Security Updates, but the price will increase on a yearly basis.

For most organizations, however, a migration to Windows 10 should be at the top of their New Year's resolutions. Microsoft recommends upgrading to Windows 10, and it's the most secure way to receive new feature updates.

Here are some tips to ensure that an organization is ready for the Windows 7 deadline for support.

Check application compatibility

A legacy application is often a troublesome but necessary component of an organization's infrastructure. As such, legacy applications are frequently one of the biggest hurdles of Windows 10 adoption. There are a few steps that organizations can take to ensure that legacy applications don't impede the Windows 10 migration.

First, IT admins should perform an inventory on the organization's existing applications. Admins can do this through the use of scanning tools, such as Microsoft Assessment and Planning Toolkit or SolarWinds' network audit tool. Scanning tools can create reports that enable IT to identify problematic applications. Next, IT should check with all its application vendors to ensure that their existing line-of-business applications are Windows 10-compatible.

Other helpful tools to test application compatibility include Windows Assessment and Deployment Kit and Windows Analytics in Azure. These are both free tools provided by Microsoft.

A Windows 10 migration is often required by the business, but IT admins should also look at it as an opportunity.

The last step is to perform a test upgrade to Windows 10. During a test upgrade, IT admins will be able to spot any troublesome behaviors and address them.

Approach migration as an opportunity, not a requirement

A Windows 10 migration is often required by the business, but IT admins should also look at it as an opportunity. An upgrade is a good time to consider adopting new tools or modernizing areas of the IT infrastructure.

Admins can use a Windows 10 migration as an opportunity to implement a unified endpoint management (UEM) platform, for example. A UEM platform can streamline device management and ease the migration process. When considering a potential UEM tool, IT should see how it handles application and user data, which deployments it supports and how it integrates with third-party tools, among other factors. Organizations that have already deployed UEM should ensure that their existing platform meets these criteria as well.

Organizations can also consider supporting multiple OSes during a Windows 10 migration. The emergence of cloud services and SaaS applications makes it easier for organizations to manage multiple OSes. Supporting both macOS and Windows 10 gives users more flexibility and mobility and, in certain departments, may be necessary.

Avoid staying on Windows 7 if possible

Organizations can still install and activate Windows 7 after the Windows 7 deadline in January, but the reasons for doing so are extremely limited. Support for a variety of Microsoft applications, such as Internet Explorer and Office 2019, end with the deadline, which makes working on a Windows 7 desktop unstable and less secure. Microsoft, however, will provide security updates for Office 365 until January 2023, but the program will not receive feature updates if Windows 7 is still running on the device.

One of the only valid reasons to continue running Windows 7 is if the organization uses a mission-critical application that is incompatible with Windows 10. Even still, those organizations should limit Windows 7 to isolated devices and prioritize replacing the unsupported application.

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