High resolution calibrated infrared imagery of the Space Shuttle was obtained during hypervelocity atmospheric entries of the STS-119, STS-125 and STS128 missions and has provided information on the distribution of surface temperature and the state of the airflow over the windward surface of the Orbiter during descent. This data collect was initiated by NASA's Hypersonic Thermodynamic Infrared Measurements (HYTHIRM) team and incorporated the use of air-and land-based optical assets to image the Shuttle during atmospheric re-entry. The HYTHIRM objective is to develop and implement a set of mission planning tools designed to establish confidence in the ability of an existing optical asset to reliably acquire, track and return global quantitative surface temperatures of the Shuttle during entry. On Space Shuttle Discovery's STS-119 mission, NASA flew a specially modified thermal protection system tile and instrumentation package to monitor heating effects from boundary layer transition during re-entry. On STS-119, the windward airflow on the port wing was deliberately disrupted by a four-inch wide and quarter-inch tall protuberance built into the modified tile. In coordination with this flight experiment, a US Navy NP-3D Orion aircraft was flown 28 nautical miles below Discovery and remotely monitored surface temperature of the Orbiter at Mach 8.4 using a long-range infrared optical package referred to as Cast Glance. Approximately two months later, the same Navy Cast Glance aircraft successfully monitored the surface temperatures of the Orbiter Atlantis traveling at approximately Mach 14.3 during its return from the successful Hubble repair mission. In contrast to Discovery, Atlantis was not part of the Boundary Layer Transition (BLT) flight experiment, thus the vehicle was not configured with a protuberance on the port wing. In September 2009, Cast Glance was again successful in capturing infrared imagery and monitoring the surface temperatures on Discovery's next flight, STS-128. Again, NASA flew a specially modified thermal protection system tile and instrumentation package to monitor heating effects from boundary layer transition during re-entry. During this mission, Cast Glance was able to image laminar and turbulent flow phenomenology optimizing data collection for Mach 14.7. The purpose of this paper is to describe key elements associated with STS-119/125/128 mission planning and execution from the perspective of the Cast Glance flight crew that obtained the imagery. The paper will emphasize a human element of experience, expertise and adaptability seamlessly coupled with Cast Glance system and sensor technology required to manually collect the required imagery. Specific topics will include a near infrared (NIR) camera upgrade that was implemented just prior to the missions, how pre-flight radiance modeling was utilized to optimize the IR sensor configuration, communications, the development of aircraft test support positions based upon Shuttle trajectory information, support to contingencies such as Shuttl...