A pressure support system configured to deliver a pressurized flow of breathable gas to the airway of a subject is further configured to provide information to a user position, fit or seal between the subject and the patient interface through which the pressurized flow of breathable gas is delivered. Such information may include, for example, a location on the patient interface at which the integrity of the seal is compromised, adjustments that could be made by the subject to enhance the interface between the patient interface and the subject, different types and/or sizes of patient interfaces that could be used to enhance the fit and seal between the system and the subject, and/or other information.