Obstructive sleep apnea (OSA) is an acute breathing disorder, which causes soft tissue inside the throat to collapse, thus blocking the airways while sleeping. This syndrome is usually treated by the supply of pressurized air delivered by a pump, which is connected to the patient via mouth and/or nose using a mask as an interface. While most of the literature on OSA is focused on the pressure pump and the therapy conditions (pressure, humidity, velocity, etc.) there has been an increased interest in the mask/interface as a key contributing factor to the treatment's effectiveness. Mask-related issues such as skin damage, allergic reactions, or air leaking due to poor fit can deter OSA patients from following this treatment. This study presents a preliminary evaluation of customized mask designs, which are tailored to specific wearer's facial contours. The development process includes the use of three-dimensional scanning/modeling/printing as an integrated workflow. Individual facial features have been digitally acquired and used to generate a custom device, which conforms to predefined facial landmarks of interest, which delimit the mask contour. A trial study was undertaken by recruiting two healthy volunteers for the fit and comfort evaluation of custom mask designs using a randomized fit test with a series of three-dimensional (3D) printed versus commercial standard mask. Results indicate that custom masks exhibit a higher level of comfort compared to conventional continuous positive airway pressure (CPAP) masks particularly on fit, contact pressure and comfort.