Over some decades of doing development work on legacy systems - sometimes by my companies own design, sometimes contract work for a customer - I've seen lots of things that make me believe that certain customers do prefer complex, buggy software for a very specific reason:

They can hide behind it. "I couldn't finish the task on time because the software had a bug" - sort of stuff. "I couldn't do X because the software doesn't support Y", "The dog ate my homework", etc.

In many cases, it would have been quite possible to design simple, easy and far less bug-prone solutions - but then people working with the software would no longer be able to hide that certain failures might be due to their own incompetence, rather than being a software issue. Therefore - especially in companies with high top-down pressure - people actually prefer working with software that their managers don't fully understand, and that's known for having some bugs and problems.