The family Kogiidae, comprising the pygmy sperm whale (Kogia breviceps) and the dwarf sperm whale (K. sima), represents some of the least-known cetaceans worldwide. Their small size, deep-diving behaviour, and elusive surface activity result in very few live sightings, particularly in the North Atlantic Ocean. Here, we report two significant observations from the Azores in July 2025: a group of six K. breviceps, the largest reported group size of this species, and a confirmed sighting of K. sima off Pico Island – representing only the sixth record for the archipelago. Photographic evidence and expert validation confirmed the identification of K. sima based on body proportions. We also review records of both species, including other live encounters and strandings, across the Macaronesian archipelagos (Azores, Madeira, Canary Islands, and Cape Verde). Together, our observations and synthesis document an exceptional group size for K. breviceps, emphasise the rarity of K. sima in the region, and highlight the value of whale-watching platforms and citizen science for monitoring elusive cetaceans.