Specifically after more and more of the incestuous relationship between the FAA and Boeing comes to light.
Including claims that experienced engineers, which were in charge for certain certifications were demoted or fired if they were too critical or outright refused to certify certain sub systems as was reported in the Seattle Times[1]
It seems that since 2004 engineers in charge of certification were stopped to communicate directly with techies at the FAA, but reported to their managers, which in turn communicated with the FAA.
He who pays the piper calls the tune.
[1] https://www.seattletimes.com/business/boeing-aerospace/engin...
American Airlines (a life long Boeing customer) placing a massive order of 320NEO put Boeing into full throttle panic mode and triggered the unfortunate decision to apply yet a number of hacks to an airframe, which was not suitable for the purpose.
I was about to snark, "Sometime prior to people dying as a result of the debt."
But then I considered that (potentially) the $X dollars saved by allowing the technical debt to live on, could probably be invested in some other way that saves far more lives. I.e., obesity reduction, smoking cessation programs, etc. So perhaps the issue isn't that simple.