A roof insulation fastening system employs a fastener and a compression plate with a tube which interacts with the compression plate to permit the plate to vertically move relative to the head of the fastener when the adjacent area and/or plate is subject to excessive compression. The tube includes a retainer shoulder and a pair of tabs wherein the plate captures the tube. The tube includes a throat and a tapered portion with a throughbore. The fastener is inserted into the tube and secured in place so that the head is retained at the intersection of the throat and the tapered portion and the shank is secured into the roofing substrate.