High resolution calibrated near infrared (NIR) imagery was obtained of the Space Shuttle's reentry during STS-119, STS-125, and STS-128 missions. The infrared imagery was collected using a US Navy NP-3D Orion aircraft using a long-range infrared optical package referred to as Cast Glance. The slant ranges between the Space Shuttle and Cast Glance were approximately 26-41 nautical miles at point of closest approach. The Hypersonic Thermodynamic Infrared Measurements (HYTHIRM) project was a NASA Langley led endeavor sponsored by the NASA Engineering Safety Center, the Space Shuttle Program Office and the NASA Aeronautics Research Mission Directorate to demonstrate a quantitative thermal imaging capability. HYTHIRM required several mission tools to acquire the imagery. These tools include pre-mission acquisition simulations of the Shuttle trajectory in relationship to the Cast Glance aircraft flight path, radiance modeling to predict the infrared response of the Shuttle, and post mission analysis tools to process the infrared imagery to quantitative temperature maps. The spatially resolved global thermal measurements made during the Shuttle's hypersonic reentry provides valuable flight data for reducing the uncertainty associated with present day ground-toflight extrapolation techniques and current state-of-the-art empirical boundary-layer transition or turbulent heating prediction methods. Laminar and turbulent flight data is considered critical for the development of turbulence models supporting NASA's next-generation spacecraft. This paper will provide the motivation and details behind the use of an upgraded NIR imaging system used onboard a Navy Cast Glance aircraft and describe the characterizations and procedures performed to obtain quantitative temperature maps. A brief description and assessment will be provided of the previously used analog NIR camera along with image examples from Shuttle missions STS-121, STS-115, and solar tower test. These thermal observations confirmed the challenge of a long-range acquisition during re-entry. These challenges are due to unknown atmospheric conditions, image saturation, vibration etc. This provides the motivation for the use of a digital NIR sensor. The characterizations performed on the digital NIR sensor included radiometric, spatial, and spectral measurements using blackbody radiation sources and known targets. An assessment of the collected data for three Space Shuttle atmospheric re-entries, STS-119, STS-125, and STS-128, are provided along with a description of various events of interest captured using the digital NIR imaging system such as RCS firings and boundary layer transitions. Lastly the process used to convert the raw image counts to quantitative temperatures is presented along with comparisons to the Space Shuttle's onboard thermocouples.