An optical signal quality monitoring apparatus includes a trajectory length acquirer measuring a Stokes vector of an optical transmission signal over an optical signal modulation frequency band and acquiring the length of a trajectory in the optical signal modulation frequency band traced out on a Poincare sphere by the measured Stokes vector as the measurement value; a DGD acquirer acquiring a DGD value of the optical transmission signal the Stokes vector of which is measured by the trajectory length acquirer; and a quality value estimator estimating a quality value by using the length of the trajectory acquired by the trajectory length acquirer and the DGD value acquired by the DGD acquirer.