The combination of a building roof section and a flashing repositioning apparatus. The roof section has an upwardly facing surface, with an edge at which there is a fascia, and a depending flashing portion. The flashing repositioning apparatus has a flashing engaging assembly and a manipulating assembly. The flashing engaging assembly has a body defining a wedging surface and a guide surface. The guide surface is configured to be consistently located in a predetermined operative position against the fascia surface wherein the wedging surface is at a predetermined angle relative to the fascia surface. The wedging surface resides between the fascia surface and the flashing portion to define a gap into which a wall of a gutter can be directed.