The tail assignment problem is a critical part of the airline planning process that is tasked with satisfying the operational constraints for all aircraft. The aim of this paper is to develop an operationally flexible tail assignment that satisfies short-range---within the next three days---aircraft maintenance requirements and performs the aircraft/flight gate assignment for each input line-of-flight. While maintenance plans commonly span multiple days, the related tail assignment problems can be overly complex and provide little recourse in the event of schedule perturbations. The presented approach addresses operational uncertainty by extending the one-day routes aircraft maintenance routing approach to satisfy maintenance requirements explicitly for the current day and implicitly for the subsequent two days. A mathematical model is presented that integrates the gate assignment and maintenance planning problems. To increase the satisfaction of maintenance requirements, an iterative algorithm is developed that modifies the fixed lines-of-flight provided as input to the tail assignment problem. The tail assignment problem and iterative algorithm are demonstrated to effectively satisfy maintenance requirements within appropriate runtimes using input data collected from three different airlines.