A bit tip insert on a bit/holder, tool, and/or pick for road milling operations that includes a body including a tip and a base subjacent the tip The bit tip insert also includes at least one heat transfer bore extending from a distal end and/or bottom of the body to a bore termination disposed within the base and/or the tip of the bit tip insert. The at least one bore of the bit tip insert is adapted to allow inward contraction when the overlay transfers heat into the base during operation.