A medical dressing (100) with a dressing body (102) and a flap (104). The flap can include a fixed end (120) coupled to the dressing body, and a free end (122) movable with respect to the dressing body between a first position and a second position in which the free end is positioned in overlapping relationship with the dressing body. A second major surface (116) of at least the free end of the flap can be configured to be secured to the dressing body, and the flap can be located toward a proximal end of the dressing body, such that a distal portion of the dressing body is free of the flap. The dressing body can be adhered to skin with a skin-contact adhesive (e.g., a silicone adhesive) (115), and the flap can be secured to the dressing body with a securing adhesive (e.g. an acrylate adhesive) (117) that can have a higher adhesion or adhesive strength.