A suicide where the deceased has employed more than one means of ending his or her life is defined as a complex suicide (CS). Forensic practitioners may face difficulties caused by the articulated mechanisms underlying this event. Among CS, the combination of hanging and gunshots is unusual. In this study, we present three unique cases of such planned complex suicides (PCS) that we have encountered in our 28 years of activity at the Bureau of Legal Medicine of Milan. Careful inspection of the death scene, precise analysis of the anamnestic-circumstantial data, and accurate medico-legal autopsy examination were the starting points for a better understanding of the causes and manner of death. In particular, the presence of vital reactions of tissues involved in the two different means used, the coherence of the areas involved with a self-inflicted wound, and the absence of signs of third party intervention allowed us to classify these events as suicides. As for the chronology of events, the lethality of the cerebral lesions caused by the gunshots in all cases, in accordance with the cervical lesions caused by hanging, led us to conclude that we were dealing with PCS and catalogue these three cases as unusually planned complex suicides avoiding incorrect and superficial classification.