A scalp scratching assembly for penetrating a hair accoutrement without disturbing the hair accoutrement includes a shaft that has an adjustable length. At least one pad is coupled to an end of the shaft. The at least one pad is textured. The at least one pad may abrade a users scalp. The at least one pad is insertable through the hair accoutrement. The hair accoutrement remains stationary while the shaft is moved. The at least one pad scratches the users scalp.