Security

What Small Businesses Need to Know About Windows 10 End of Life

As the deadline for upgrading to Windows 11 rapidly approaches, teams must consider hardware compatibility and Microsoft’s extended security updates program.

Nathan Eddy

Nathan Eddy works as an independent filmmaker and journalist based in Berlin, specializing in architecture, business technology and healthcare IT. He is a graduate of Northwestern University’s Medill School of Journalism.

On October 14, Microsoft’s Windows 10 will officially reach end of support, which means the company will no longer provide free software updates, technical assistance or security fixes.

As a result, organizations must tightly monitor legacy systems and be prepared for more aggressive patching using third-party tools.

For Forrester Senior Analyst Paddy Harrington, even stopgap security measures may be short-lived. “At some point, those third-party vendors are going to stop supporting Windows 10,” he says.

Since Windows 11 shares a foundation with its predecessor, organizations can rely on existing deployment solutions such as Microsoft Intune and Endpoint Configuration Manager.

To streamline their transition to Windows 11, businesses can apply the same management infrastructure used for Windows 10 because the operating systems are designed to coexist, allowing organizations to manage updates, applications and deployments.

Microsoft recommends that once hardware eligibility is confirmed, businesses should evaluate their current deployment infrastructure and update management processes to support a smooth and scalable migration.

Experts also recommend that organizations review and update their servicing strategies to accommodate the differences in Windows 11 support and rollout timing.

Click the banner below to learn how CDW can help streamline your Windows 11 migration.

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Why Does the Windows 10 EOL Matter?

The risk organizations face by not upgrading in a timely fashion isn’t that systems will stop working, it’s that they will become vulnerable, Harrington explains.

“If a new bug comes out that is a security vulnerability, there’s no patch coming,” he says. “Any approaches to mitigating that vulnerability have to be done through other security tools.”

Organizations must factor these support limits into both short-term risk planning and long-term IT modernization strategies.

Businesses must be realistic about the October Windows 10 end-of-support deadline. Small businesses may find it easier than others to migrate to the new OS, Harrington says, but for many, “you’re not going to hit the deadline.”

Application compatibility, even more than hardware, is one pressing challenge, says Ryan Reith, group vice president for IDC’s Worldwide Device Tracker suite.

This can complicate migration timelines depending on how deeply custom software is embedded in operations.

EXPLORE: CDW services that simplify the migration to Windows 10 Pro.

What Are the Challenges of Upgrading to Windows 11?

Cost and IT readiness are two of the biggest hurdles organizations struggle with as they migrate to Windows 11, Reith notes.

While some companies have already invested in compatible hardware during past upgrades, lingering reliance on niche or legacy software can prevent a full migration.

“It’s usually not the big names like Adobe or Salesforce. It’s proprietary or unknown names,” Reith says.

For those, updating or replacing core business apps remains the final hurdle.

Harrington urges organizations to test thoroughly for application compatibility issues.

“If you still have a compatibility problem, you must start finding other ways to deliver that application,” he says. “There is a compatibility mode in Windows 11 that allows you to run it on the endpoint, often without a problem.”

At some point, those third-party vendors are going to stop supporting Windows 10.”

Paddy Harrington Senior Analyst, Forrester

How Can Your Small Business Prepare for Windows 11?

Before migrating to Windows 11, organizations should evaluate their IT environment — including the number of endpoints and physical devices — to ensure hardware compatibility.

“Any new hardware from the past three to four years can support Windows 11,” Harrington says. But even on supported hardware, application and user acceptance testing are critical.

However, the biggest pitfall is trying to migrate too many users at once. “Plan to migrate in stages because then, if there’s a problem, it’s easier to roll it back,” he says.

Businesses should also be realistic and expect failures and delays. “Plan to have 10% of your enterprise on Windows 11 by the October date,” Harrington says.

Organizations may also need to buy extended support or accept short-term security risk. “Pay attention to that end-of-support date, because it’s going to come, and you’re going to have to do this all again,” he says.

DIG DEEPER: Build a foundation for smarter device management with a Windows 11 upgrade.

On the organization side, it’s going to be a collaborative effort between the CIO and his IT team members as they focus on infrastructure, devices, applications and security, Harrington says.

IT staff must determine which systems are impacted, especially when considering virtualized workloads or compatibility workarounds. Meanwhile, security teams must monitor unsupported virtual machines for vulnerabilities.

“IT has to be aware of any security alerts coming off that endpoint,” Harrington says.

To help users through the transition, Microsoft offers a paid Extended Security Updates program for businesses. CDW complements this with a comprehensive suite of services, including readiness assessments, Windows Autopilot deployment, IT asset disposition, configuration and deployment assistance, plus around-the-clock, personalized technology support.

For a fee, businesses can receive extended security support until Oct. 10, 2028. Small businesses, especially, might find this a compelling offer. “For a company that has maybe 100 PCs, the option to extend is worth considering,” Harrington says.

UP NEXT: Avoid hidden risks and shift to Windows 11 now.

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