The problem is a lack of modularity and standardised interfaces where it matters (and modularity where it doesn't, causing additional useless complexity), and incentives that reward planned/forced obsolescence.
Also related: TLS 1.3 on Windows 3.11: https://news.ycombinator.com/item?id=36486512
I’d say that complexity is the other part of the problem. As developers, we like to organize functionality into packages, and version them based on the type of changes we make. We like layers of abstraction to contain classes of problems to work on them independently. But all software is a list of instructions, and all the ways that they can interact cannot be categorized in a Symantec version number, or a unit test. Subtle changes can break functionality in surprising ways.
There's a discussion to be had that's the volume of E2E vs unit tests, but that isn't this discussion.
I can change from ext2 to btrfs and my program won't die because open and read are a good interface.
The only solution is to have a crystal ball.