Heat Shield Causing Issues Installing Spark Plug Boots

Of all the ridiculous things to get hung up on, this is just aggravating. I'm trying to put plug wires on the drivers side of my '67 273, but with the heat shield in the way, there is not even close to enough room for my big hands to hold the boot and snap it into place. The edges of those shields are sharp and I'm going to end up with bloody hands. I'm using a stock set of wires from Napa. Anyone have a trick to getting those things on there?