If you have multiple holes, you need to select the point at the center, then the contour of each hole before you move to the next hole. Each hole needs a point followed immediately by the associated chain.

I made some screenshots for the benefit of those not running MC2020. Geometry: select the point at the center of the hole, then the contour. Depth cuts: UNCHECK "Keep Tool Down" Lead-in: use entry point Lead out: NO EXIT POINT. Very important. use a perpendicular exit less than the center distance. Multi-Passes: CHECK "Keep Tool Down" Linking: Make your clearance high enough to clear the chips. UNCHECK "Use clearance only at start and end..." These settings will retract to the clearance plane at the end of each depth level. Press single block as it comes up and blow out the chips. Alternatively I suppose you could create a sequence at each depth if you needed program stops. HTH, Steve.

I found this thread when I was having the exact same issue on MC 2020. I'm using the center of the hole for entry and retract. I deselected the "use exit point" on the lead in/out tab and set a perpendicular lead out to get the cutter off the wall. I deselected "keep tool down" on the depth cut tab, and selected "keep tool down" on the Multi Passes tab. The tool retracts after each depth for clearing chips.