There is growing interest in commercial aircraft formation flight as a means of reducing both airspace congestion and the carbon footprint of air transportation. Wake vortex surfing has been proven to have significant fuel-saving benefits; however, commercial air transportation has yet to take advantage of these formation benefits due to understandable safety concerns. The realization of these formations requires serious consideration of safety contingencies during closer-in maneuvering of large commercial aircraft. Formation contingency scenarios are much more complex than those of individual aircraft and have not yet been studied in depth. This paper investigates the utility of an optimization modeling approach in generating maneuvering and escape paths for commercial formation aircraft by comparing model-generated paths with pilot-generated escape plans. Three high-altitude commercial aircraft formation scenarios are presented: formation join, formation emergency exit, and formation escape. The model-generated paths are evaluated and compared with pilot-generated escape plans using the author’s pilot expertise. Model results compare well with pilot intuition and are useful in presenting solutions not previously considered, in evaluating separation requirements for improvement of escape path planning, and in confirming the viability of the pilot-generated plans. The novel optimization model formulation presented in this paper is the first model capable of generating exit and escape paths comparable to pilot-generated plans. It is also the first model to incorporate path avoidance of persistent and drifting wake turbulence.