This paper describes the design, manufacturing, testing, and evaluation of a novel trailing pressure measurement system by a team of student engineers as part of an undergraduate senior capstone design project. The system is intended to be self-contained, housing all transducers and subsystems internally, with the capability to mount to any Part 23 and Part 25 aircraft. The system trails behind an aircraft during flight to obtain accurate atmospheric data. The system utilizes a series of pitot-static tubes that relay information to static and differential pressure transducers. In addition to detailing the engineering design of the drogue, this paper outlines the testing campaign to validate its functionality.