The Windows 10 countdown has begun.
If your business has devices currently running on the Windows 10 operating system, you’ll need to start preparing now as Microsoft will fully transition to its Windows 11 operating system this fall.
This means that Microsoft will stop providing updates and security patches for the old OS as of October 14, 2025 as it focuses its attention on Windows 11.
After that date, you’ll no longer be able to access free updates, technical support, bug fixes, or security patches. You also won’t be able to buy new Windows 10 licenses after the deadline.
Without critical security updates, you’re essentially sending out an open invitation to hackers to try to exploit any new and emerging vulnerabilities resulting from using an end-of-support (EOS) operating system.
This will affect businesses competing in highly regulated industries such as finance, healthcare, manufacturing, automotive, and those within the defense industrial base (DIB) because they must meet stringent cybersecurity requirements.
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Using end-of-life (EOL) or EOS software and devices can also result in regulatory compliance issues, possibly leading to hefty fines or even the loss of certain contracts.
In this article, we’ll examine why you need to upgrade to the new OS. We’ll also provide a 5-step checklist you can follow to see if your devices can support Windows 11, and what you need to do if they can’t.
With this information, you’ll be able to determine your next steps to ensure that you remain compliant and that your business can continue running smoothly and securely.
Although Windows 11 has been available since October 2021, Microsoft is only now setting a firm date to pull support of Windows 10. As we mentioned, using outdated software can create a significant security risk.
Once malicious actors are able to gain a foothold into your systems, it can lead to a cascade of damages, including financial loss, reputational damage, customer churn, compliance failures, and other harm.
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Sounds a little hyperbolic, right?
Well, in January of this year, Microsoft issued Windows security patches to cover 159 vulnerabilities, including a dozen critical vulnerabilities, according to a recent Forbes magazine article.
What’s more, eight of the vulnerabilities identified with the most recent patch update were zero day threats—including three active zero day cyberattacks, Forbes reported.
A zero day attack is a new or undetected security flaw that happens before the software developer has a chance to identify and fix it.
It’s called “zero day” since it gives software developers or hardware manufacturers zero days to address the vulnerability since hackers have already started exploiting the flaw to compromise your sensitive data and IT infrastructure.
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Often, hackers will launch zero day threats on the day an operating system stops getting support, giving them a prime window to attack.
Since its release in July 2015, Windows 10 has had literally hundreds of security patches and 13 major feature updates.
With cybercriminals using increasingly sophisticated tools including artificial intelligence to infiltrate your IT systems, it’s important that you take action now.
As we’ve shown, waiting until the last minute could leave you susceptible to a zero day attack or other cyber incident.
How do I determine if Windows 11 will run on my device? What do I do if my devices can’t support the new OS?
To check whether your business hardware meets the minimum system requirements to run Windows 11, follow these simple steps:
If your existing hardware and software systems meet the upgrade requirements, then Microsoft will automatically offer you the Windows 11 upgrade through Windows Update. You’ll be able to look under settings to download the upgrade when it becomes available.
Windows Update is a free service Microsoft offers that automatically downloads and installs software updates for your Windows OS.
It can take up to 24 hours for Microsoft’s Windows Update to refresh system eligibility information, according to the company.
If the update takes longer than expected, you can also manually refresh your eligibility assessment in one of two ways.
To manually refresh Windows 11 eligibility assessment, choose one of the following methods:
If your devices don’t meet the minimum hardware requirements, you'll need to purchase new ones. Microsoft strongly discourages installing Windows 11 on unsupported devices, as you won’t receive security updates or support.
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If you’re simply upgrading from Windows 10 to Windows 11 on a supported device, then no, your existing data, account settings, and installed applications won’t be affected at all.
You should still check to make sure that your existing programs are compatible, as Microsoft will automatically remove any incompatible programs during the installation process. These programs can be reinstalled afterwards.
Keep in mind that if you perform a clean install of Windows 11 on your devices, this process will wipe all stored data on your computer’s hard drive, including personal files, apps, and customized settings.
You would need to access data backups to restore your information.
Regardless of whether you’re performing an update or clean install, it’s a best practice to ensure that you have up-to-date backups of your important information using resources including an external hard drive and cloud storage.
To be perfectly clear, not installing the new OS won’t break your machines. Your devices will still work, and you’ll still be able to connect to your network.
You could also pay for Microsoft’s extended security update (ESU) subscription program to continue getting Windows 10 security patches after October 14. The ESU program is for businesses that need to run certain legacy software past the end of support.
The program is only meant to be a temporary fix. It’s not ideal for several reasons, including that its costs double every year, and because it can lead to compatibility issues with your newer devices and software, putting your systems at risk.
In addition, if you run into a technical issue or want to take advantage of newer features, you’re out of luck since the program doesn’t extend the technical support or product updates beyond October 14.
As we mentioned above, not upgrading to a Windows 11 setup can open the door to cyber threats. It can also lead to system configuration or connectivity problems within your IT environment.
If you’re a business in Connecticut or Massachusetts and you’re unsure if your devices can support the new Windows 11 operating system, or you need help installing the new OS on your devices, Kelser Corporation has years of experience helping clients seamlessly undertake similar operating system integrations.
We also offer secure endpoint backups for your devices as part of our managed workstation and server backup solutions.
With our managed IT services, you gain a deep bench of skilled professionals with broad IT and industry expertise who work to integrate the new Windows 11 upgrade as seamlessly as possible within your organization, maximizing uptime, productivity, and efficiency.
Don’t give hackers an opening into your IT infrastructure and put business at risk.
Reach out now to schedule a device compatibility assessment and start the process to upgrade your hardware to Windows 11.