I've run across the same a time or two. I guess that the solution would be to start reviewing applications to make new purchases less proprietary and less likely to choke on newer platforms. I'm running an old WinAmp that was around with Win95 on a Win7 platform. I realize it's a lot less complicated than some of the huge apps that businesses need, but I find it difficult to understand why folks keep painting themselves into corners by having special apps contracted for development with no plan to upgrade after a certain expected life span. The companies that develop the software are the biggest winners.
On the flip side, we also try to adapt COTS apps for other than the originally intended use and that creates its own ball of wax.
A lot of our tools were custom made by small companies because the big suppliers weren’t interested in modifying their standard semiconductor tools to our needs. As a result, we had tool sets that were hard to get software updates for and many of them were orphaned.
A lot of our control software was developed in house when we were part of a much bigger company and before vendors had realized the market for off the shelf software to fulfill those functions. These were integrated shop floor and quality control systems at worldwide sites that posed significant costs and risks for changes so they were being put off as long as possible. New systems were being tried, but were still limited in scope and were rapidly increasing in complexity and cost to match the internal systems we already had.