We have some machines that still run Windows 7 at the office, while we don't use Windows 10 for anything beyond isolated testing environments. This is a result of assessing the risks of using Windows 10 as being greater overall than the risks of using Windows 7 in the relevant cases, despite the state of official support and lack of any further security patches. And that in turn is in no small part because Windows 10 has a track record of breaking things that would be important to our business operations. Newer is not always better, and being more secure in some respects is not always being more useful overall.

For your office specifically, have you looked into Windows 10 LTSC? That's my solution when I need to run Windows at home.

Yes, we did. The higher editions of Windows 10 do seem to be qualitatively different products that don't have the technical deal-breakers we are concerned about. Unfortunately, as far as we could tell, there was no (legal, properly supported) way to get hold of any of them for small businesses like ours through simple one-off purchases of permanent licences.

I have a lot I experience navigating Microsoft's licensing for small businesses. I have a Customer who needed Windows 10 LTSC for some PCs running expensive laboratory instruments as a recent example of needing to do just what you're looking for.

You can acquire a permanent license for Windows 10 LTSC through Microsoft's Open Business licensing program. There is a minimum initial purchase quantity of 5 SKUs, but any competent reseller will just pad your order with the lowest-price-in-the-catalog SKU to get you up to that minimum.

The Open License Agreement itself expires in two years, meaning that you're subject to the minimum 5 SKU purchase to start a new one at the end of 2 years. During the term of the Agreement you can purchase licenses piecemeal. Regardless of the Agreement's term the software you license thru the program is perpetually licensed.

This won't make it any cheaper, though. Windows 10 LTSC is ridiculously expensive, to me, for what it is. Licenses acquired through this program are transferable to new hardware, at least. That's why I used it a lot over the years. Buying Office and transferring it to a new PC once in the useful life ended up being a cost savings over buying OEM Office with the original and replacement PCs.

Thank you for sharing those insights.

The idea that you have to go through a dealer, join some overcomplicated volume licensing programme, possibly buy extra stuff, and probably pay a premium for the privilege just to get a legitimate copy of LTSC to use doesn't sit well with us.

If Microsoft offered LTSC as a one-time, off-the-shelf purchase with no strings attached, I expect we'd buy several copies immediately. It seems to be the only version of Windows 10 we might actually want, other than for having the same as our customers/clients for testing purposes. But as a small business, we have limited time and resources, and we have remarkably little interest in playing big business games.

I don't like it either, but that's proprietary software. Personally, I wish my Customers didn't have business-critical applications that keep them tied to Windows and other proprietary software.

I suppose my point is that it wasn't how proprietary software tended to work until relatively recently. For many years, we (assorted small businesses) were using the Pro editions of Windows with no drama. This only became an issue when Microsoft chose to make the Pro edition of Windows 10 unsuitable for professional use (in our humble opinion) while simultaneously locking the more suitable editions behind Big Organisation Hassle.

As a direct result of that decision, they have essentially lost our business, just like certain other large software organisations whose names start with A that have adopted similar customer-hostile practices in recent years. There are viable alternatives for almost anything these days when you're a small business with the flexibility to make intelligent policy decisions about your hardware and software purchases on a case by case basis and, if appropriate, to change those policies however you want later on.

I've been pretty displeased with how Microsoft has chosen to alienate Customers the last few years. I've made a good since the late 90's installing and support Microsoft software in small businesses, and the changes in the last few years, particularly with Windows 10 and the associated Server versions, have been distressing.

I will say that I've never found the Open License program to be a tremendous hassle. There was good cost savings to be had using transferable licenses, and the product use rights and other terms and conditions were clearly spelled-out. Dealing with resellers was the worst part of it, but I managed to find good resellers who would mostly just do what I asked for and not hound me with sales-gerbil nonsense. The volume license management website was actually fairly nice, and was useful for keeping track of a Customer's license inventory.

I've had a hard time getting much free/open-source software adoption in my small business Customers. They almost always have a mission-critical application that keeps them locked to Windows (or SQL Server, Office, Exchange, etc), and no budget or desire to finance software development. The value proposition of spending money on the proprietary software is often just good enough to make it worth the cost and draconian licensing.

This is very helpful. I've bought a couple of LTSBs (now LTSC) over the years through oddball means, I strongly favor it, but it seems like Microsoft doesn't want me to be able to buy the licenses. Finding less shady-seeming resellers has not been something I've been able to manage.

I agree, they're costly.