Having worked all my life in large organisations, this sounds very familiar. A lot of people would rather the company to go bust than to challenge an internal policy written by a group of people largely above their level of competence, and completely unaware and unconcerned of the implications of their policies.
One of the things you realise when you get closer to management is that those policies shouldn't be taken too seriously if they contradict common sense.
OTOH, people who risk their career to challenge an internal policy written by a group of people largely above their pay grade and not answerable to them, at best become pariahs who are ignored, and at worst are fired for "not being a team player".
Most people are only concerned with their own little corporate corner and doing the least effort that keeps them in paychecks. Trying to follow the spirit of a rule rather than the letter, or pushing for change to improve things overall, is never appreciated.
By middle management maybe. By senior management, what gets you promoted is the ability to fight back, challenge things that don't make sense and to get things done.
If your middle management is full of yes men (yes people?) it's because that's who senior leadership chose to promote. The idea that there exists some level where C-level execs in that organization are going to suddenly appreciate dissent is wishful thinking. These kinds of cultures begin at the top.
We call those people/policies the "Business Prevention Department"... In other words, they're the department that makes it difficult for everyone else to generate revenue. Sometimes they're right, but often they're too rigid to operate in reality and instead of protecting the company they actually hurt it.
One of the things you realise when you get closer to management is that those policies shouldn't be taken too seriously if they contradict common sense.