Mac Pro :: How Do You Get The Rubber Dampeners Thru The Holes

So I removed my 4th bay's tray and it seems the dampeners are not thru the holes and unless you get them half way thru the holes you cannot slide back the tray because the screws are too high and make contact with the surface.

When you have nothing to screw them into what is the best way of getting the rubber dampeners thru the holes so the screws will sit low enough in the tray to reinsert the tray?

So my final tray #4 has no drive attached but those rubber stopper things aren't easy to get thru the holes. Right now the only way I can put my track is to remove the screws entirely and keep them outside the case. I'd rather them insert into the holes of the sled that's empty but for I need those darn grey rubber things to go thru the holes.