The two types of "works"
Often when you are building software, you will ask if a particular piece is working and the developer will say yes. Then you will go test it and it won't work.
Usually this is because it does work in some cases, but it does not work in others. Getting it to work as well as it did took a lot of time and effort, and as a developer you are excited about this and focused on the things you have been paying attention to. And the things you have been paying attention to definitely work.
I don't know if we can fix our terminology, but a good follow up question is probably "does it break?" or "will it always work"? A conversation about the cases in which the software does and does not work is probably a better one anyway, the boolean was not helping anybody.