The problem is estimation errors are not symmetrically distributed because engineers chronically underestimate how long something will take, and the problem is exacerbated by management pressure giving them an incentive to estimate even lower.
We're trained to cut big problems in small parts to solve them.
This is more closely related to human psychology than pure logic.
The distribution of delays is pathological, too. It's not normal or poisson or anything nicely amenable to analysis.
Ever had a task with 4 seemingly “easy” parts where 3 are easy and it turns out 4 requires a big rewrite because of some hacked put in 8 years ago that are now deeply ingrained assumptions in the code?
Often you are asked to estimate a 10k part project!