Why is it management always waits until point of failure for a major system to hear us about replacing systems with updated systems?

"If it is not broken, don't fix it" misunderstood grossly

There is a way to present the update case to managment.

Use a made up cost analysis:
Update the system will cost X$.
The reason (whatever reason) we should update is because not upgrading can cost us Y$. And X will avoid Y cost. And as long as X<<Y - they will approve.

If they won't - ask to get this in writing. If they ask why, expalin that you will need to show that you took intiative, and want to have thier answer, in case it is needed. So in case the shit hits the fan - you have your ass covered.

The Challenger mistake... over and over and over again...

Like that shit job where I asked the manager of my manager for backup hardware for the build machine server and for PC parts. We did not have any and IT did not care.

I was told this was just a money drain and that there won't be any problems. Imagine waiting 2 weeks for parts to repair a broken machine (shitty forced supplier) and not being able to work because your company is too retarded to understand business finance and risks 101.

@PepeTheFrog and they can't setup a build server in some Cloud?

@asgs hard to do when there is CI to do on embedded hardware

If they can't see the problem, they won't care about the solution.