When a bolt, plug, ect is tightened, it has a tendency to stretch the base material and pull the threads up around the hole preventing the two parts from seating properly. In high performance engines and where the fit is critical, the top thread in the hole is gently removed leaving a slight taper in the top of the hole to eliminate this problem.
You can do the same using a countersink bit.
One other thing that I do is place the copper washer on the plug with the cup of the washer (the new washer is not flat) away from the plug, toward the head. When I install the plug, I always tighten the plug down and loosen it several times, progressively getting tighter, to seat the washer. The copper washer also helps to transfer the heat from the plug to the head and if full surface contact is not made, it can cause the plug to run hotter.
This may seem like overkill, but my plugs do not leak at all.
Just my way.
Charles