During the NASA/FAA Tailplane Icing Program, pilot evaluations of aircraft flying qualities were conducted with various ice shapes attached to the horizontal tailplane of the NASA Twin Otter Icing Research Aircraft. Initially, only NASA pilots conducted these evaluations, assessing the differences in longitudinal flight characteristics between the baseline or clean aircraft, and the aircraft configured with an Ice Contaminated Tailplane (ICT). Longitudinal tests included Constant Airspeed Flap Transitions, Constant Airspeed Thrust Transitions, zero-G Pushovers, Repeat Elevator Doublets, and, Simulated Approach and Go-Around tasks. Later in the program, guest pilots from government and industry were invited to fly the NASAT win Otter configured with a single full-span artificial ice shape attached to the leading edge of the horizontal tailplane. This shape represented ice formed due to a “Failed Boot” condition, and was generated from tests in the Glenn Icing Research Tunnel on a full-scale tailplane model. Guest pilots performed longitudinal handling tests, similar to those conducted by the NASA pilots, to evaluate the ICT condition. In general, all pilots agreed that longitudinal flying qualities were degraded as flaps were lowered, and further degraded at high thrust settings. Repeat elevator doublets demonstrated reduced pitch damping effects due to ICT, which is a characteristic that results in degraded flying qualities. Pilots identified elevator control force reversals (CFR) in zero-G pushovers at a 20° flap setting, a characteristic that fails the FAR 25 no CFR certification requirement. However, when the same pilots used the Cooper-Harper rating scale to perform a simulated approach and go-around task at the 20° flap setting, they rated the airplane as having Level I and Level II flying qualities respectively. By comparison, the same task conducted at the 30° flap setting, resulted in Level II flying qualities for the approach portion, and Level III for the go-around portion.The results of this program indicate that safe and acceptable flying qualities with an ICT condition, can be effectively assessed by task-oriented pilot maneuvers. In addition, other maneuvers such as repeat elevator doublets provide good qualitative and quantitative assessments of pitch damping and elevator effectiveness, which are characteristics that correlate well with pilot task ratings. The results of this testing indicate that the FAR 25 zero-G pushover maneuver, which requires no CFR during its execution, may be an overly conservative pass/fail criteria for aircraft certification.