Indeed I have! My current job is at a big corp but so far I've not yet encountered something that heinous. I'm sure that we deal with vendors that bad in some p

Indeed I have! My current job is at a big corp but so far I've not yet encountered something that heinous. I'm sure that we deal with vendors that bad in some parts of this massive org, though. The quality of tools we have to work with seems to vary a lot from department to department. Why do businesses spend insane amounts of money and go through painfully slow and laborious sales and purchase processes to buy software that is utter garbage? Is it most likely to happen when their needs are highly specialized, so there's just not much competition? I know that enterprise software often has terrible or dated UX, and I understand the reasons for that. But beyond the UI, why is software that costs $5 million more likely to be shoddy and carelessly made than software that costs $50?