Business people will blame Microsoft if some security upgrade breaks proprietary software that they paid a fortune for and use daily. They're less likely to blame the developer of the proprietary software, who may or may not be willing to sell them an "upgrade," if the developer is still around at all.
When a security upgrade breaks something in the open source world someone fixes it, the programs get recompiled, and life goes on. Some software in the various Linux and BSD repositories is truly ancient by computing standards yet it still works the same as it ever did.
Windows can't always work like this. Instead it has to recognize older proprietary software and apply some ugly kludge in the operating system itself to keep the old software running. Eventually the tower of crap collapses and Microsoft is forced to discontinue support entirely for things like VBScript.
The first serious operating system I used was BSD, in the late 'seventies and early eighties. I eventually migrated to Windows, mostly so I could use modern web browsers such as Opera. The last version of Windows I used on my home computers was 98SE. When I quit that for Linux it was like going home again. A lot of the stuff I'd been doing with BSD "just worked," including my finger memory. The stuff that didn't work I could fix myself or, more likely, someone else had already had the same problem and fixed it. I wasn't dependent upon the whims or business models of any proprietary software company or developer to fix it for me.