Pressure sensitive adhesives for use primarily in medical applications are disclosed. The pressure sensitive adhesives are urethane elastomeric adhesives that include a polyurethane polymer and a compatible tackifier and/or compatible plasticizer to achieve an adhesive having a predetermined compliance. The result is a pressure sensitive adhesive for application to skin that can eventually be removed with very little trauma to the skin and with a low pain rating, but which still exhibits very good peel strength when used to construct an article in which the adhesive is adhered to human skin.