> Does management continually deprioritize critical "keep the lights on" work eg security patches WHEN they are fully aware of the repercussions (this knowing is key.)

One variant is when Management punishes you for bringing something up by making it your task to then fix it. I think they don't do this on purpose, they often just don't think about it. And it leads to a culture of "don't tell the boss". I've seen some really dire problems swept under the carpet because of this.