Applications of flow aid devices such as inserts improve the silo discharging mode. Considerable effort has been made in finding the best configurations between inserts and silos to achieve optimal functional results. In the present investigation, experiments were carried out to measure the loads imposed on a double-cone insert by particulate solids (free-flowing sand) when it was fitted within an axisymmetrical large-scale silo. Concentric filling/discharging was implemented to carry out such measurements. Pressures along the walls of the silo were also measured. Analyses of the measurement results showed that: (1) the loads on the insert were rather stable in total, but appeared to be asymmetrical at the end of filling; (2) a sudden increase of the loads on the insert was observed at the transition from filling to discharging, but this increase lasted only for a short moment; and (3) the loads on the insert decreased slowly but remained rather high for a large part of the discharge. Effects of the double-cone insert on the pressures along the silo walls were discussed.