We discuss the case of a 26-year-old woman who presented with pelvic pain and recent onset vaginal bleeding in early pregnancy. Transvaginal USS identified significant free fluid in the pelvis associated with a right adnexal mass and an empty uterus. A ruptured ectopic pregnancy was suspected, and the patient was taken to theatre for an emergency laparoscopy. Paradoxically, the procedure found no signs of intra-abdominal blood loss. Instead, a large, unruptured 20cm ovarian cyst filled the right adnexa and Pouch Of Douglas (POD), extending posteriorly towards the pelvic brim. It was a right Ovarian, Dermoid cyst. Surprisingly, the dilemma is not unique. We identified similar reports in the literature where unsuspected ovarian pathology is discovered at the time of early pregnancy surveillance, often masquerading as an acute complication of early pregnancy. In this report, the patient went on to have a spontaneous miscarriage, and the cyst was later removed by mini- laparotomy. We present this case as an opportunity to highlight the epidemiology of adnexal pathology presenting for the first time in early pregnancy and to help broaden clinical suspicion when considering potential diagnoses at the time of presentation.