Bryan and Jim make two good electrical points.
To say it a slightly different way, the GFCI circuit breaker will see the "bleed current" of the branch circuit and that will "use up" part of the 3 to 4 milliamp current "buffer" that is required to flow before the GFCI will trip.
This means, that a tool, say, that has a high impedance connection to ground resulting in a ground fault of 2 milliamps whenever energized, will trip the GFCI circuit breaker that already has a 3 to 4 milliamp leak.
The same tool, with 2 milliamp ground fault, will not trip the GFCI receptacle that it is plugged into because the leak in the branch circuit happens on the line side of the GFCI.
What I have just described is electrical behavior as designed. There is nothing in the Code about this.