The problem for this falls directly on vendors that make their crap hard to keep up to date. I'm not blaming Microsoft for this, as they're actually pretty decent - the problem usually is with 3rd parties that don't validate on the newest releases.

Seriously people - there's a reason OS vendors have prerelease software programs. If you're not testing your software on say the Windows 8 beta or on prerelease versions of OS X 10.7.3, then when it doesn't work on day one of release it's likely your fault, not the OS vendor for breaking stuff.

The larger issue is that software testing is a PITA... this is probably a shared issue between Dev and Ops. Every time I see a new single function "installs software X outside of package management" program, I have to think that both sides are doing the other a disservice. Dev's should be able to get their software on multiple platforms easily, and Ops shouldn't have to wrestle to get it installed. We've only been wrestling with this problem for the last 30 years...