Rectangular prism-shaped cargo containers are investigated for future aerial delivery and helicopter sling load operations. The aerodynamic stability characteristics of two representative container shapes, the Twenty-foot-equivalent (TEU) and Internal Slingable Unit (ISU®)-90, are analyzed using a combined computational simulation and wind tunnel experimentation campaign. Integrated forces and moments, as well as static stability, are examined for the two shapes at Mach of 0.15, and 0.2. Six models are used in total, three for each of the two container shapes, with axial, normal, and side orientations. The findings provide insights into the aerodynamic stability of rectangular prisms as cargo containers in various flight conditions, which have implications for aerial delivery and helicopter sling load operations. Specifically, the computational simulations and experimental surface flow measurements identify flow separation and reattachment processes which directly influence longitudinal, lateral and directional stability characteristics.