I think the root of this are 3 things:

1. Failures are not fun or interesting, of which they should be. Which leads to…

2. Everyone (including the GM) is trying to avoid the failures by piling on bonuses, re-rolls, bennies, and whatever. There’s no motivation to justify the bonuses because no one at the table wants a failure, which leads to…

3. Why even make it a roll? Just Gumshoe it and give it to them or just tell them to enjoy the ride on the railroad.