In the crowded world of supraglottic airway devices (SADs), many papers compare the easiness of insertion based on the different endpoints of an operator’s satisfaction: first pass success, ventilation effectiveness, complications and morbidity. Proseal LMA^™ (Laryngeal Mask Airway, Teleflex Medical, Dublin, Ireland) has been extensively studied because on one hand it has a steeper learning curve and more complex insertion when compared with other SADs and on the other hand many alternative techniques are available to facilitate insertion. This research is part of a larger body of studies exploring the issue that some devices are more difficult to insert because of many features related to sizing, constructive material, airway conduit and cuff design, performance and last but not least experience. Nevertheless, the biggest question might be the search for a systematic categorization of insertion difficulty features and identification of criteria allowing the choice for the best device and consequently for the best insertion technique. Given that, as a result of many intrinsic characteristics of the device we are using, insertion might become the secondary issue to be considered only after we clearly identify what makes it difficult, and to be counterbalanced on the results we expect from the device, performance we can achieve and degree of airway protection it could grant. The aim of this narrative review is to consider which factors might affect or condition SAD insertion difficulty and to try identifying some criteria addressing physicians pertaining to the use of SADs in clinical practice.