Can't use pre-drill entry unless "Keep Tool Down" is enabled?

[FrodoLoggins]

Why not?

[oleg.tikhomirov]

Hi @FrodoLoggins,

This is by design. Transitions from drill position to cutting paths are considered as part of stay-down moves so "Keep tool down" must be enabled to allow them. Moreover "Maximum stay-down distance" should be big enough. Otherwise operation might fail with the following warning:

[programming2C78B]

it has to....that's the (w)hole point of picking a drill point center. 

Take a peek at using a Circular toolpath for this feature, you may enjoy the enter/exit at center function.