It will follow the hole/bore if the drill is on size or smaller than the hole. I run into an issue with solid tools(drills) that are built on size but the engineer makes the hole to a rounded number like a .4375 diameter drill and an engineer makes the hole at .437 forgetting to add the .0005 it will not drill that hole because the drill is too big . I ask the engineers to always round the hole diameters up whenever possible to like .438 diameter.
If they don't do this (which is quite often) I then have to change the model myself or force the drill through the hole. I don't like forcing the drill because it is more work for me to drill to a depth because I have to take extra time to measure the depth and add it to the drill or find or make a surface do set the depth to.
This is a big source of frustration to me because of engineering ignorance!!
OK, that must be an issue with using solid tools then. If you are not using solid tools, I am pretty sure you can put any size drill into any given hole size.