Five new records are presented on the presence of two rare cephalopod species (Argonauta argo (Linnaeus, 1758) and Ocythoe tuberculata (Rafinesque, 1814)) in the waters of the Autonomous Region of Madeira, Portugal. Increased collaboration with fishermen has made it possible to significantly add to the number of records in the region, and further collaboration may provide key insights into the ecology of these rare cephalopod species.