Fossil galaxy systems have been described as some of the oldest systems in the universe, where the central galaxy has cannibalized most nearby member galaxies over cosmic time. While the progenitors to fossil systems have been predicted to exist in numerical simulations, little effort has gone into locating them until now. The discovery of fossil progenitors in the CASSOWARY catalog of strong gravitational lensing demonstrates that not all fossils are old, and their formation histories are more complex than originally thought. These progenitors have optical characteristics consistent with them being the transition phase between non-fossils and fossils, as we are observing the central galaxies in mid-assembly. We also identify a bias where systems acting as strong gravitational lenses are ~5 times more likely to be seen as fossils than non-lensing systems. Chandra X-ray images of eight CASSOWARY fossil progenitors show them being significantly over-luminous and hotter than comparable non-fossils which could be due to the strong lensing bias in our data, or fossils have characteristically deeper potential wells than non-fossils. Two progenitors were luminous enough to see a rise in gas temperature toward their cores which suggests these may be undergoing group mergers akin to the previously studied progenitor CSWA 2 verifying this as a viable fossil formation mechanism. Refinements to our original CASSOWARY data using the Hubble Space Telescope allowed us to disentangle complex merging environments at the centers of these eight progenitors, which further solidified the notion that progenitors are indeed transitioning toward fossil systems.