A window dressing includes a primary layer having a window for viewing a catheter insertions site. The primary layer includes an adhesive layer on a lower, skin-contacting face of the primary layer. A transparent layer covers the window and adheres to the patients skin and to the top surface of the primary layer. A support structure has a stiffness that is greater than the primary layer and has an adhesive layer on the lower surface of a structural layer of the support structure. The support structure adhesive layer adheres to the support structure to the top surface of the primary layer.