While January may have lasted 7,000 years, October will be here before you know it. And Halloween isn’t the only spooky thing that comes up in October. It’s not just candy corn that is coming, but Windows 10 End-of-Life. October 14, 2025 is the date set for the end of support for Windows 10. NOW is the time to act to make sure that your systems are updated so that you can keep your business running smoothly and your data protected.

What does End-of-Life even mean?

End-of-Life is when Microsoft stops providing updates, including ever-important security patches that keep your systems safe from evolving cyberthreats.

Once Microsoft stops supporting Windows 10 on October 14, 2025, your systems will no longer receive security updates. This will leave your PCs vulnerable to the latest cyber threats and malware, creating significant risks to your business, data, and client information.

Yea, but won’t it still work? I mean we have antivirus software…

You may think that you have antivirus software in place, and you will be okay. And while antivirus software does help, it relies heavily on the underlying security of the operating system. Without regular OS patches, your defenses will have major gaps that antivirus alone cannot cover. Hackers specifically target unsupported systems because they know those vulnerabilities won’t be fixed. Thinking a system that has reached end-of-life is safe because you have antivirus software is the equivalent of rolling up the windows on a convertible and thinking you won’t get robbed, never mind the top is down, your doors are unlocked, and the keys are tucked in the sun visor.

Eek…this sounds expensive

We get it. Security can sometimes be uncomfortable. But in the same way a seatbelt is more comfortable than a head through a windshield, it is always less painful to be proactive when it comes to security measures.

Upgrading your systems now can avoid the much larger costs of emergency upgrades, lost productivity, or dealing with a potential security breach. Planning ahead allows you to phase in upgrades at a manageable pace, which is easier for your budget and operations.

Delaying the upgrade means higher risk — and potentially higher costs down the road. Emergency replacements tend to be far more expensive, not to mention the downtime if you’re hit with a security breach. Working out a phased upgrade plan, spreading costs over time, can make the upgrades more manageable.

And, you may not want to hear this, but… you have to upgrade if you expect your insurance to help in the event of a breach.

You do not have to eat candy corn this October, but if you want your systems to maintain compliance with cyber insurance and industry regulations, you need to be able to receive system updates and security patches. Insurance companies often deny claims related to breaches if the systems are not patched or up to date. Imagine trying to report your car stolen but then having to confess you left the top down, doors unlocked, and oh yeah, you may have left your keys in the car too.

Cyber insurance companies are tightening requirements, and unsupported software is a red flag for them. Imagine having a breach and then finding out your insurance won’t cover the damage because your systems weren’t compliant. It’s better to stay ahead of these requirements to avoid costly surprises down the line.

The Benefits of a Gradual Transition in the Face of Windows 10 End-of-Life

Starting your upgrade process now means you can phase it in over time, minimizing disruptions and helping your budget more effectively. This way, your business stays protected and compliant without overwhelming you with costs all at once.

Delaying plans to upgrade puts your business at risk because many businesses will also be upgrading, which could create delays in getting hardware or scheduling services. If everyone rushes at the same time, you might face supply chain issues, longer wait times, and increased costs. Starting now gives you priority access to the hardware and services you need, and we can avoid scrambling at the deadline.

When it comes to cybersecurity, no one can afford to procrastinate. Failing to upgrade from Windows 10 after its end of support (EOS) has severe consequences.

The most immediate impact of Windows 10 reaching its end of support is the ending of routine security updates. Without these updates, your system becomes vulnerable to new and evolving online threats, exposing it to potential security breaches and malware attacks. Additionally, technical assistance for Windows 10 will no longer be available, leaving users without access to Microsoft's support services. Any existing documentation will become part of historical archives.

As support for Microsoft Windows 10 ends, the ecosystem will fragment, impacting software compatibility and functionality over time. Thus, the end of support for Windows 10 signifies the end of a secure and sustainable computing environment for its users.

To ensure a seamless transition and to avoid any disruptions in your operations, ProActive Information Management strongly advises that you begin scheduling your upgrades to Windows 11 as soon as possible. Any devices that do not support the upgrade to Windows 11 will need to be replaced. It is crucial to allow adequate time for to complete these orders and replacements. We recommend that all replacement quotes and orders are signed by Spring of 2025 to ensure that you will have all you need to meet the Windows 10 EOL deadline with relative ease.

Let’s make sure that when October comes around, the only spooky thing on your horizon is too much Candy Corn.