Latest / The Windows Podcast with Fexingo: Microsoft, PC, and Enterprise Windows Conversations / Why Windows Enterprise Upgrades Keep Getting Pushed Back
Transcript
- Lucas: If today's tech conversation gave you something usable — a number you hadn't seen, a decision framework that actually maps to your environment — here's the honest economics behind this show. A small group of listeners chips in monthly through buy me a coffee dot com slash fexingo, and that's what keeps these episodes ad-free and focused on the specifics that matter. Luna: Yeah, and it's not a big ask — it's just that without that support, a show digging into enterprise upgrade cycles and app compatibility testing doesn't get made. So if you've gotten value from any of these episodes, that link is the reason we can keep going. Lucas: Right. And speaking of upgrade cycles — let's talk about the elephant in the IT room. Enterprise Windows 11 adoption is stuck at around 35 percent in large organisations. That's according to a survey from Lansweeper published in March. Two and a half years after Windows 11 launched, nearly two-thirds of enterprise endpoints are still on Windows 10. Luna: And that number hasn't budged much from last year. I remember seeing similar figures in early 2025. Lucas: Exactly. So what's driving this inertia? It's easy to blame IT departments for being slow, but the data tells a more nuanced story. I've been looking at a specific case — a mid-sized manufacturer in the Midwest with about 4,000 endpoints. They started testing Windows 11 in early 2024, and they're still not fully deployed. Luna: What's the holdup for them? Lucas: App compatibility — but not in the way you'd expect. They have about 120 line of business applications, most of them custom-built over the last 15 years. Some are written in older frameworks that Microsoft has deprecated. They spent roughly $1.2 million testing those apps on Windows 11 24H2. And after all that, 8 percent — about 10 applications — still break under the new OS. Luna: So even a seven-figure testing budget couldn't catch everything. That's a hard sell to the CFO. Lucas: Right. And those 10 broken apps aren't trivial — they include a custom inventory management system and a tool that interfaces with their warehouse robots. The vendor that wrote the inventory system went out of business in 2022. So there's no upgrade path. The IT team is now looking at either virtualising those apps or keeping a few Windows 10 machines on a segregated network. Luna: That's the kind of legacy debt that doesn't show up in a Microsoft compatibility report. You only find it when you actually run the app. Lucas: Exactly. And it's not just apps — driver certification is another bottleneck. I talked to a hardware compatibility engineer who works at a large laptop manufacturer. He told me that for Windows 11 24H2, Microsoft tightened the driver signing requirements significantly. Any driver that doesn't meet the new Windows Hardware Quality Labs standards simply won't load. That means older peripherals — barcode scanners, receipt printers, industrial sensors — may stop working. Luna: So even if the OS itself is stable, the ecosystem of devices around it might not be. For a manufacturing floor or a warehouse, that's a showstopper. Lucas: Precisely. And the cost of testing those peripherals at scale is enormous. One logistics company I read about had to certify 47 different models of handheld scanners across their distribution centres. Each certification took an average of three weeks. Multiply that by 47, and you're looking at nearly three years of full-time work just for scanners. Luna: Which brings us back to the timeline. Microsoft has set October 14, 2025 as the end of support date for Windows 10. That's less than five months from now. Lucas: Yeah, and that deadline is real — no more security patches, no more updates. But many enterprises are already planning to pay for Extended Security Updates. Microsoft offers three years of ESUs for Windows 10, priced per device, and the cost increases each year. For a company with 10,000 endpoints, year one alone could be $600,000. Luna: So the choice is: spend hundreds of thousands on staying put, or spend millions on migrating. Neither is cheap. Lucas: And the migration cost isn't just testing — it's also re-imaging. Replacing hardware that doesn't meet Windows 11's TPM 2.0 and processor requirements. A lot of enterprise PCs bought in 2019 and 2020 simply can't run Windows 11 natively. So you're looking at a hardware refresh cycle that might cost $1,000 to $1,500 per machine, plus deployment labor. Luna: And that's assuming the supply chain for enterprise PCs is stable. We've seen shortages before. Lucas: Right. So the rational calculation for many IT departments is to delay as long as possible, pay for ESUs, and use that time to test more thoroughly. The risk of a botched upgrade — a critical app going down — could cost far more than the ESU fees. Luna: But there's also a risk in waiting. If you wait too long, you might be forced into an accelerated migration when Windows 10 support ends, and that could be even more chaotic. Lucas: That's the tension. Microsoft knows this, which is why they've been offering tools like the Windows 11 Readiness Assessment and the App Assure program — free support for app compatibility issues. But those tools only go so far. They can't rewrite a custom app that was built on a now-defunct framework. Luna: So what's the smart move for an IT leader listening right now? Lucas: I think the smart move is to do a rigorous inventory — not just of hardware, but of every application and peripheral. Categorise them by criticality and by vendor support status. Then build a testing lab that mirrors your production environment as closely as possible. Start testing the most critical apps first. And if you find a broken app, don't assume you can fix it — start looking at alternatives or workarounds now, not in September. Luna: And budget for ESUs as a fallback. Even if you plan to migrate by the deadline, having ESUs in your pocket gives you a cushion if something goes wrong. Lucas: Exactly. Look at the manufacturing company I mentioned — they've already budgeted for two years of ESUs on a subset of machines that run those broken apps. That's probably the most pragmatic approach. Accept that some legacy workloads will stay on Windows 10 for a while, and secure them with ESUs and network segmentation. Luna: It's not a perfect solution, but it's realistic. And it buys time for the industry to catch up — for app vendors to update their software, for hardware makers to certify drivers. Lucas: Right. And that's the thing — enterprise IT isn't about being first to adopt. It's about keeping the business running while managing risk. The 35 percent adoption rate isn't a failure. It's a reflection of the complexity underneath. Luna: So next time someone asks why your company isn't on Windows 11 yet, you can point to the eight percent of apps that break, or the 47 scanners that need recertification. It's not laziness — it's due diligence. Lucas: Exactly. And with that October deadline approaching, the due diligence window is closing. If you haven't started testing yet, today is the day to begin. Luna: Good advice. On that note, thanks for listening to The Windows Podcast with Fexingo. We'll be back with another deep dive soon.