Windows 10 End of Life: Your Business Game Plan

The full conversation from the webinar above, lightly edited for readability. Timestamps mark each section.

0:00 · Welcome & Introductions

Ken: Good morning, everyone — thank you all for attending today’s webinar, “Windows 10 End of Life: Your Business Game Plan.” My name is Ken Widmer, Chief Technology Officer at Macro Technology Group. With me today is Nicholas Frangopoulos, our technical account manager.

Today we’re going to talk about a critical transition: the end of Windows 10 support. While Windows 10 end of support is still ahead of us, in IT terms it’s right around the corner — planning, upgrading, security hardening, and compliance reviews all take time, and waiting too long can leave your organization scrambling. Our goal is to help you understand what’s changing, why it matters, and how to proactively build a plan that keeps your business secure and ready.

0:52 · What We’ll Cover Today

Ken: We’ll cover what’s happening and when; what’s at risk if you wait — from compliance failures to cyber insurance to application support; the consequences of delaying; and some myths about upgrading, because there’s a lot of misleading information out there. We’ll take a quick side-by-side demo of Windows 10 and Windows 11 and go over the new features. Some older devices won’t make the cut, so we’ll help you identify which ones, assess compatibility for the ones that can upgrade, and walk step-by-step through getting your devices ready. We’ll share a five-phase strategy, give you tips to avoid delays and unnecessary costs, cover how Macro can support your transition from audit to deployment, and close with Q&A.

2:03 · What’s Happening — and When

Ken: Windows 10 goes end of life on October 14, 2025. Your computer will still work on October 15th, but after that date Windows 10 will not receive any more updates, bug fixes, or security patches — including patches for zero-day vulnerabilities. It also means Microsoft won’t offer support for any Windows 10 issues, and neither will most application vendors. When something breaks — an app crashing, a security bug, or a compliance problem — there’s no support to fall back on.

We’ve seen this before with other operating systems that reach end of life: key applications like Chrome, Office, and Adobe drop support, stop making updates, and eventually stop working.

3:00 · What’s at Risk If You Wait

Ken: Security vulnerabilities — an unsupported operating system becomes a magnet for attackers, and each month that passes increases your exposure. Regulatory non-compliance — frameworks like NIST, HIPAA, PCI, and SOC 2 mandate that all systems remain supported and regularly patched; falling behind puts you at risk for audit failures, fines, and compliance issues. Cyber insurance carriers are following suit — many policies now ask whether all operating systems are supported and patched, so running an unsupported OS that can’t be patched can result in claim denials.

3:51 · Why Unsupported Systems Are a Target

Ken: Unsupported systems are a known target for attackers — they’re often the easiest point of entry. Operating systems require regular updates to stay secure, and once support ends, so do the critical fixes. Attackers actively look for out-of-date systems because the vulnerabilities are well documented, and without patches those weaknesses stay wide open.

4:18 · Why Planning Ahead Saves Money

Ken: The longer you wait and the closer it gets to end of life, the more expensive and harder it will be to get new hardware, because demand will ramp up. Planning ahead means better pricing, more choices, and less stress — and it gives your IT team time to simplify the rollout.

If you wait, rush upgrades often lead to downtime, frustration, and last-minute scrambling. Waiting too long usually means doing it during business hours under a tight deadline; planning ahead lets your IT team schedule it during nights and weekends, limit disruption, allow testing, and make the migration go smoother.

5:08 · Myths About Upgrading

Ken: “Windows 11 is just a cosmetic upgrade.” Not true — it includes significant performance improvements, enhanced security architecture, and new features like snap layouts and faster DirectStorage.

“Upgrading will break your apps.” Microsoft reported that 99.7% of apps work across Windows 10 to Windows 11 — most mainstream applications will work perfectly; if one doesn’t, it’s most likely an older compatibility issue that wasn’t supported in Windows 10 either.

“Windows 11 is slower.” Actually the opposite — Windows 11 is more efficient, with better hardware utilization, faster boot times, and improved battery life. “You must buy new hardware.” You might, but not always — devices from the past few years may already be compatible. “You can’t go back.” Technically you can roll back within 10 days of upgrading, but we’ve seen no reason to move back once you’re on Windows 11.

6:39 · Windows 10 vs. Windows 11: The Start Menu

Ken: Here we have Windows 10 on the left and Windows 11 on the right. The first thing you’ll notice is the Start menu placement — on Windows 10 it’s on the left; on Windows 11 it’s closer to the center. The Start menu itself has been redesigned: Windows 11 shows pinned applications, and to see everything you click the All button. To add an app like Outlook, right-click it and “Pin to Start.” If you run out of room, right-click free space, open Start settings, and choose a personalization layout with more room for pins. The other functions are the same, just relocated — power settings and sign-out moved to the right, near the bottom.

8:16 · File Explorer: Tabs & Easier Copying

Ken: In File Explorer, Windows 10 made you right-click to copy, open another Explorer window, and paste — or click through folder levels and back each time. Windows 11 consolidates that: copy, open another tab in the same window, navigate, and paste — or just drag between two panes to move files. A lot less clicking.

9:34 · Snap Layouts & Virtual Desktops

Ken: On Windows 10 it was hard to snap windows to the size you wanted. Windows 11 fixes that with Snap Layouts — hover the maximize button or drag a window to the bar at the top, then pick a layout: left/right, 50/50, or four small windows. Windows even helps pick the second app to fill the other half — no guesswork.

The other big productivity feature is virtual desktops: click the two overlapping squares in the taskbar to create a new desktop. It’s useful if you wear different hats — keep one desktop just for a task (like this webinar) and switch back to your normal Outlook-and-web-apps desktop when you’re done. Whatever you set up on each desktop stays through a reboot. Those are the top four features we get the most feedback on.

11:40 · Do You Need New Hardware?

Ken: Here are the specs Windows 11 requires: a TPM chip, UEFI with Secure Boot, a 64-bit processor (32-bit is no longer supported), 4 GB of RAM, and 64 GB of storage. Our recommendations are higher — at 4 GB of RAM the experience will be very slow. We recommend 16 GB of RAM and a 256 GB solid-state drive. Rough estimate: if you bought the device in 2020 or earlier, you’re most likely looking at new hardware; if later, you can most likely upgrade.

12:39 · Assessing Device Compatibility

Ken: To know for sure, start by getting a list of all your devices — an asset-management or RMM tool works well; we use our RMM to gather every device we’re looking to upgrade. Then run Microsoft’s PC Health Check application (download it from Microsoft, or run it from your RMM). It gives a pass/fail report per device based on its hardware — telling you whether it’s compatible, whether you need to upgrade the RAM or drive, or whether it needs an outright replacement.

13:35 · Macro’s Five-Phase Upgrade Strategy

Nicholas: Thank you, Ken. I’m Nicholas Frangopoulos, technical account manager at Macro Technology Group. I’ll walk through an upgrade plan using Macro’s five-phase strategy: Identify, Prioritize, Budget, Procure, and Deploy.

Identify — build a comprehensive inventory of every device running Windows 10 or below (desktops, laptops, any hardware); we use our RMM platform for this. Prioritize — rank devices by how critical they are to operations; key departments like finance, leadership, and customer service should go first. Budget — estimate the cost of new hardware, software licenses, and any additional resources.

Procure — buy the necessary hardware and software, upgrade the compatible devices, and replace the ones that aren’t. A device should ideally be under four years old and covered by an extended warranty to be worth upgrading rather than replacing — otherwise a machine that fails mid-upgrade has to be repaired or replaced at cost, which we don’t advise. Deploy — install the hardware and software, configure the devices, and confirm everything works. Following these five phases ensures a smooth, efficient transition with minimal disruption.

17:32 · Hardware & Procurement Tips

Nicholas: Start procurement early — none of us are strangers to lead times and vendor supply issues, so getting ahead avoids a last-minute rush. Choose business-grade hardware with a warranty — typically no less than three years — for reliability and better support during the transition.

Review your overall hardware needs, and look for bulk discounts if you’re buying multiple devices: if a machine is teetering on the recommended replacement age, including it may push you to a volume-discount threshold. Factor in lead times and vendor delays so you have enough time to receive and set up hardware before October. And ask for help when you need it — from IT experts or your vendors.

19:59 · How Macro Can Help

Nicholas: First, we audit your environment — a thorough review of your hardware and software to check Windows 11 compatibility. Then we do a risk assessment, identifying gaps and how to close them with our proactive approach. Based on that, we recommend the best upgrade path — which devices to upgrade, replace, or reconfigure.

Our team can manage the entire deployment, from procuring new hardware to rolling out upgrades with minimal disruption. We offer training sessions on Windows 11’s features and interface so your team is ready. And we make sure your systems are secure, recommending or implementing measures to protect your data and prevent breaches.

21:44 · Q&A

Ken (most underrated Windows 11 features?): For me it’s virtual desktops. I wear a lot of different hats, and being able to partition applications across desktops and switch back and forth keeps everything clutter-free and organized. For this webinar I have a desktop that’s just this webinar; when I’m done I close it and go back to my normal Outlook-and-web-apps desktop.

Nicholas (how long to help a 50-employee company?): First we identify and audit — reviewing your inventory’s age and what needs upgrading versus refreshing — then I quote replacements and we assess how many devices need upgrading. Procurement timing depends on vendor lead times.

Ken: On the technical side we use the crawl-walk-run method — start with the first few PCs, let them burn in, assess hardware and software, and flag likely issues before rolling out to the whole fleet. The upgrade itself takes a couple of hours per device, and we can roll back if needed. For 50 computers you could be fine within a week if pushed, but we typically like a two-week crawl-walk-run window.

Nicholas (better to procure through Macro?): Emphatically yes. As an MSP we do a lot of business with many vendors, and those relationships typically get us better pricing — especially on volume orders and large refresh projects.

Ken (most common specs clients choose?): We mentioned the i5 processor and the newer Ultra 5 / Ultra 7 and 14th-gen Intel lines, plus a 256 GB SSD as the lowest we’d recommend. Applications are more resource-intensive now, so a lot of clients stick with an i7 or Ultra 7 and go bigger on storage — 512 GB or 1 TB SSDs.

Ken (issues when an upgrade fails or hits bare-minimum specs?): With bare-minimum storage the upgrade won’t run, or takes a very long time; sometimes antivirus causes issues if it isn’t disabled first — usually sorted out in your first batch. If you do run bare-minimum specs it’ll work, but it’ll be slow.

Nicholas: On storage specifically — as an SSD fills up you’ll hit performance issues, another reason clients go larger. Keep at least 20% of your drive free for max performance; below that, a process called TRIM can’t work efficiently and the SSD’s buffers get turned off.

30:26 · Closing

Nicholas: We hope you found this informative. The recording will be emailed. Feel free to reach out to book a free consultation — I’m Nicholas Frangopoulos, technical account manager at Macro, your one-stop shop for everything IT.