Countersink Holes and Drill File

Make it a callout on the Fab drawing.   Pretty sure this is an unusual request to put a threaded fastener into a plated hole in the first place. 

Foreign Objects and Debris:  FOD.  Makes for tiny bits of copper to be chipped off and get loose in the assembly while the screw is installed.

Bring attention that this holesize on the drill table needs to be countersunk to stated dimension in the primary drill process before plate and etch.

We do a simple trick.  Let's say we have an 0.062" hole that's standard and one that's non-standard such as yours.  We use two drill dimensions: 62 and 62.1.  That way each hole has a separate entry in the drill table.  We got this method from the major fabricators who are used to this.  Of course, there needs to be an associated note somewhere on the drawing which mentions the special handling of the "62.1" drill.  And human contact prior to fabrication helps.  I always preview these drawings with my fabricator and make sure we are sync'd up before sending.  In a company that blindly sends out fab data for lowest bidder you might still run into an issue with this method.

I'm with RFinley - show it on the fabrication drawing, in a Detail. One thing - "Plated" counter-sink hole? Never done it in my career. Not sure why you need it plated, but that's your decision. But, detail it, and highlight it in the drill legend.

There is a checkbox on the NC Drill form to include counterdrill (countersink/counterbore). If this is enabled a jobname-cd-TOP.drl file is generated as well as the usual drill files.

The one problem I have with counter-sink and counter-bore holes is the padstack editor only defines the 'counter-' from the topside. It would be helpful if the editor would flip the 'counter-' accordingly. I'm not one to mirror the holes in the layout and depend on that to get translated properly to the fabricator, so I clearly define the 'counter-' holes in the fabrication drawing.