Windows 11 for Law Firms: Costs, Risks, and the Easiest Way to Upgrade

Our partner and Chief Information Officer, Sarah Ellis, sat down to discuss what Security Information Event Management (SIEM) is and why it is important. The conversation has been lightly edited. You can read a summary below or watch the video here: https://youtu.be/u8GYroOSrV0

Trey Hiller: Hi, everyone! I’m Trey Hiller, Director of Sales and Marketing at Clear Guidance Partners. Today, I’m joined by Sarah Ellis, our Chief Information Officer and walking knowledge bank. We’re here to talk about something important and time-sensitive: the Windows 11 upgrade. Many firms are still on Windows 10, or even older, and may not realize there's a looming deadline. Sarah, can you help us understand why upgrading to Windows 11 matters, what risks are involved if firms don’t upgrade, and what that process looks like?

Sarah Ellis: Absolutely. First, the critical deadline is October 14, 2025. After that date, Microsoft will no longer provide security updates or patches for Windows 10. While your machine will technically still work, it won’t be protected, meaning hackers who already know about vulnerabilities will take advantage of them. This puts your firm’s network at serious risk. It could also jeopardize your cybersecurity insurance. Some policies might not cover breaches if your systems are out of date, or your premiums could spike.

Trey Hiller: So, not upgrading could cost a firm a lot more in the long run.

Sarah Ellis: Exactly. The good news is, if you're using Windows Pro or Business editions, the upgrade is completely free. If you're on a Home version, we strongly recommend upgrading to Pro; it’s better for business use anyway. That said, some older machines, typically those over six years old, can’t support Windows 11. In those cases, firms will need to replace those machines before the deadline.

Trey Hiller: Once firms have compatible devices, how hard is it to actually upgrade?

Sarah Ellis: It’s simple. At Clear Guidance, we’ve automated the process. We coordinate with each client, pick a night when no one needs to work late, and ask everyone to save their work and leave their machines powered on and connected to the internet. Overnight, we run the upgrade automation. The next morning, users have Windows 11 and can get straight back to work. We've had zero issues with this—it’s seamless.

Trey Hiller: That's amazing. So firms working with Clear Guidance don’t just stay compliant—they do it with zero disruption.

Sarah Ellis: Exactly. We make it easy to stay secure and ahead of the curve.

Trey Hiller: Thanks, Sarah! I know this info will be really valuable for our clients and anyone else managing IT at a law firm.