Infrared observations of hot massive stars and their environments provide a detailed picture of mass loss histories, dust formation, and dynamical interactions with the local stellar medium that can be unique to the thermal regime. We have acquired new infrared spectroscopy and imaging with the sensitive instruments onboard the Spitzer Space Telescope in guaranteed and open time programs comprised of some of the best known examples of hot stars with circumstellar nebulae, supplementing with unpublished Infrared Space Observatory spectroscopy. Here wepresent highlights of our work on the environment around the extreme P Cygni-type star HDE316285, providing some defining characteristics of the star's evolution and interactions with the ISM at unprecented detail in the infrared.