Secret to getting trim sensor through transom shield

[superpop]

Hi folks, I replaced the trim sensor on my 96 VP SX drive and got it all hooked up and dialed in but am wondering what the trick is to getting the ribbed plug seated into the transom shield, I dont really want to pull the drive to seat this little bugger but I greased it up and tried pulling it into the shield by pulling on the wires but I dont want to damage the wires by pulling too hard, any ideas.