Where I am, our code doesn't work with newer versions of a dependency library. Two developers have tried to work around the incompatibility, and failed. So until we can scrounge together enough time to redevelop the frontend from scratch, we're stuck installing old versions of the library, and just hoping that no OS changes render older versions of the library inoperable - otherwise we won't be able to upgrade OSes either.
That said, this doesn't fit the topic, because our boss knows all of this. We keep our boss well in the loop. He used to work as a programmer the software, and still does some work on it from time to time. That's IMHO how it should be.
Things work best when workers aren't afraid of their boss. I hate Machiavellian workplaces.