This study aimed to explore the directional stability issues of a previously studied light box-wing aircraft model with a pusher propeller engine in the fuselage aft section. Earlier configurations have included the use of fuselage together with a lifting system consisting of two wings joined together at their wingtips with vertical stabilizers. However, these side vertical surfaces failed to provide the aircraft with sufficient directional stability, thus prompting the quest in this study for novel solutions that would exclude the need for a fuselage extension and a typical fin. Solutions included the use of a ducted propeller and few configurations of small “fishtail” vertical fins, which formed part of the aft fuselage itself and coupled with vortex generators on the fuselage surface to improve their interference and heal flow separation at the fuselage aft cone. The results of wind tunnel testing were supported with CFD simulations to explain the flow behavior of each of the studied solutions. Tuft visualization and computed flow patterns allowed identification of the sources of the observed low efficiency in terms of directional stability of the fishtail against a simple idle duct without a propeller. A final configuration with a duct and a modified version of the fuselage fins was achieved that provides enough yaw stability margins for a safe flight.