The patch of thermal paste on the cooler doesn't need extra.
My guess is that one or more push pins didnt seat correctly.
You were right! haha I still haven't left went to go check the 2 top pins are not even in they are just locked that seems to be it only one problem now. The top right pin doesn't seem like it wants to go through I feel if I press any harder I will break the board....
Edit: I see what the issue is the pin that seemed like it is jammed is.... Its not correctly lined up that was the issue testing out in a sec.