A filling machine and a filling monitoring method monitor the condition of a pressure roller and do not harm the quality of fluid food. The filling machine includes a first rotary member inside of the joining surface of a longitudinally sealed portion of a packaging material being fed; a second rotary member disposed in opposition to the first rotary member with the packaging material pinched therebetween; a rotation detection signal generator for generating a rotation detection signal in association with rotation of at least one of the first and second rotary members; and a monitoring processor for reading the rotation detection signal and detecting abnormality of rotation of at least one of the first and second rotary members. Damage to the inner surfaces of the packaging material or to the strip tape, and dropping of a sticking resin piece into fluid food contained in the packaging material are prevented.