A method carried-out by a flight planning system including a display device and a pilot input interface, the method comprising: generating a baseline flight plan, which includes at least one supersonic flight plan segment, in accordance with flight plan criteria entered via the pilot input interface, wherein the flight plan criteria entered via the pilot input interface include starting waypoint (origin) ending waypoint (destination) and Estimated Time of Departure; establishing whether an overpressure event is forecast to occur at selected intervals along the supersonic flight plan segment due to a predicted sonic boom having a magnitude exceeding a boom tolerance threshold; if an overpressure event is forecast to occur at a particular interval along the supersonic flight plan segment, determining whether the forecast overpressure event can be resolved through an acceptable modification to the baseline flight plan, wherein the acceptable modification to the baseline flight plan is one that is modified within acceptable limits; and if determining that the overpressure event cannot be resolved through an acceptable modification to the baseline flight plan, generating a corresponding visual notification on the display device; if determining that the forecast overpressure can be resolved by any one of multiple acceptable modifications to the baseline flight plan, identifying an optimal flight plan modification from the multiple acceptable modifications; modifying the baseline flight plan in accordance with the optimal flight plan modification; and wherein identifying an optimal flight plan modification comprises prioritizing flight plan modifications involving aircraft deceleration to supersonic speeds over flight plan modifications involving alterations to aircraft altitude; and wherein identifying an optimal flight plan modification comprises prioritizing flight plan modifications involving limited alterations to aircraft altitude over flight plan modifications involving aircraft deceleration to subsonic speeds. generating a baseline flight plan, which includes at least one supersonic flight plan segment, in accordance with flight plan criteria entered via the pilot input interface, wherein the flight plan criteria entered via the pilot input interface include starting waypoint (origin) ending waypoint (destination) and Estimated Time of Departure; establishing whether an overpressure event is forecast to occur at selected intervals along the supersonic flight plan segment due to a predicted sonic boom having a magnitude exceeding a boom tolerance threshold; if an overpressure event is forecast to occur at a particular interval along the supersonic flight plan segment, determining whether the forecast overpressure event can be resolved through an acceptable modification to the baseline flight plan, wherein the acceptable modification to the baseline flight plan is one that is modified within acceptable limits; and if determining that the overpressure event cannot be resolved through an acceptable modification to the baseline flight plan, generating a corresponding visual notification on the display device; if determining that the forecast overpressure can be resolved by any one of multiple acceptable modifications to the baseline flight plan, identifying an optimal flight plan modification from the multiple acceptable modifications; modifying the baseline flight plan in accordance with the optimal flight plan modification; and wherein identifying an optimal flight plan modification comprises prioritizing flight plan modifications involving aircraft deceleration to supersonic speeds over flight plan modifications involving alterations to aircraft altitude; and wherein identifying an optimal flight plan modification comprises prioritizing flight plan modifications involving limited alterations to aircraft altitude over flight plan modifications involving aircraft deceleration to subsonic speeds.