Turns out my bench top is too thick by about 2 1/2 inches. I bored out 3 dogs and tried my holdfast and it wasn't setting. So I did a practice dog hole in an edge cut off. First tried to counter bore a 1 inch hole 2 1/2 inches in the bottom but it still wasn't enough. So I opened and squared the hole to 1 1/8 with a chisel. Seems to work just fine. Problem though... Gotta turn my bench back over and chisel from the bottom. Which also means I need to re-smooth the top.