Where it starts to go badly off the rails is when there's a company culture of worse is better and one quickfix, bandaid solution is piled on top of another.
They then wind up with one or more Leaning Towers of Pisa made up of bandaids, hacks, and quick fixes, and everyone running around like headless chickens putting out fires and trying to bandaid all the failures as the towers are constantly in the process of collapsing.
This leads to an ever widening spiral of hacks upon hacks upon hacks as company culture, lack of manpower, and pennypinching never gives them the luxry of doing it right, and cutting the gordian knot by scrapping everything and doing it right from the start becomes ever more impractical.