The answer to whether a roofing contractor will need to enter your home depends entirely on the nature of the repair. While a roofer can perform most repairs entirely outside the home, a large leaky roof repair job may require the contractor to enter the home. In this case, if there’s water damage or some kind of structural damage resulting from the leak, the contractor may need to enter your home to address these issues. Leaking roof repairs are really the only repair job that may require the contractor to enter your home, and even then, it depends on whether the leak has resulted in additional damage.