In this paper we evaluate new retrievals of the deuterium content of water vapor from the Aqua Atmospheric InfraRed Sounder (AIRS) with aircraft measurements of HDO and H2O from the ObseRvations of Aerosols above Clouds and their intEractionS (ORACLES) field mission. Single footprint AIRS radiances are processed with an optimal estimation algorithm that provides a vertical profile of the HDO/H2O ratio, characterized uncertainties, and instrument operators (or averaging kernel matrix). These retrievals are compared to vertical profiles of the HDO/H2O from the Oregon State University Water Isotope Spectrometer for Precipitation and Entrainment Research (WISPER) on the ORACLES NASA P-3B Orion aircraft. Measurements were taken over the Southeast Atlantic Ocean from 31 August to 25 September 2016. HDO/H2O is commonly reported in delta-D notation, which is the fractional deviation of the HDO/H2O ratio from the standard reference ratio. For collocated measurements, the satellite operator (averaging kernels and a priori constraint) is applied to the aircraft profile measurements. We find that AIRS delta-D bias relative to the aircraft is well within the estimated measurement uncertainty. In the lower troposphere, 1000 to 800 hPa, AIRS delta-D bias is −6.6‰ and the Root Mean Square (RMS) deviation is 20.9‰, consistent with the calculated uncertainty of 19.1‰. In the mid-troposphere, 800 to 500 hPa, AIRS delta-D bias is 6.8‰ and RMS 44.9‰, comparable to the calculated uncertainty of 25.8‰.