Am I asking too much?

It's not Microsofts fault, it's not the game developers fault either.

The software was designed prior to Windows 10. Whilst some support/updates would be the right thing to do, they are not obliged to either.

I'd say 'source' it elsewhere, you paid/own it - certainly no moral issues as far as I can see.

IMO they are releasing software for the Windows platform and should make an effort to maintain compatibility with future patches, service packs and updates whether to 7 or a future OS within reason - though at the same time 6+ years is starting to push the boundaries of what I'd expect in the way of continuous support even for commercial software (unless it was subscription paid).

What I haven't quite understood yet is why you don't just run it on W7, say via dual-boot?

If he has used his 7 key as an upgrade to 10 that would mean buying a new version of 7 to do that.
 
I understand what you're saying, but I see it as an emotional response above all - in that most of us dislike DRM, and most of us despise rootkit-esque DRM. So when that's what gets in the way of software running, it's infuriating. If we strip that out of the equation, it becomes the question 'if the game is designed for W7, it should also work on W10' and I'm not convinced by that argument. I can see that it becomes even more frustrating because they have actually re-released it to work on W10, but again that will have taken up dev time etc, and whilst it's debatable whether it ought to be given out for free to buyers of the old version, I don't think you could argue that it's a requirement for them to do so.

What I haven't quite understood yet is why you don't just run it on W7, say via dual-boot?

He shouldn't have to dual boot?

The issue isn't the software, the software works in Windows 10. The issue is the DRM they have on their discs to install. It simply doesn't work due to Windows 10 removing the required SECDRV.SYS file.

So as a company that decided to go on a route to use a DRM to install on discs, you would at least expect them to help him. He bought the product, regardless of how long ago and reasons why it can't be installed. It's really bad customer service, regardless of who is to blame.
 
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