<p>As Urban Air Mobility (UAM) is developed and brought into fruition via electric vertical takeoff and landing (eVTOL) vehicles, contingencies associated with this new distributed electric propulsion technology in metropolitan areas must be considered. On the state of knowledge on contingencies for eVTOL vehicles, these can be Epistemological Risks or Ontological Risks. Epistemological Risks include known-knowns (probabilistic risks) and known-unknowns (gaps in knowledge). Ontological Risks include, unknown-knowns (hidden knowledge), unknown-unknowns (fog of ignorance). As UAM operations at large scale do not have as much historical accidents data as General Aviation or Commercial Aviation, it is challenging to estimate its accident failure rate per 100,000 flight hours. While battery thermal runaway, battery energy uncertainty, software issues, and common mode power failures are some failure cases listed in this thesis, it is the undiscovered contingency (i.e., unknown-unknown) or unprepared contingency (i.e., unknown-known), along with other external factors, that can lead to an accident. UAM is expected to operate at 1500 feet AGL and at high frequencies over dense metropolitan areas. In an in-flight emergency at these altitudes, any startle response experienced by on-board or remote pilots can lead to longer response times. This study aims to create a framework for contingency planning and risk mitigation using a Reachable Ground Footprint model for eVTOL aircraft under 100% power failure scenarios in-flight. This framework utilizes all existing, public aerodrome infrastructures in metropolitan areas as potential contingency landing sites. Metrics such as Contingency Landing Assurance Percentage and Cruise Altitude Floor requirement are introduced to quantitatively measuring the safety of any UAM trip and provide recommendations on safe cruising altitudes. A demonstration case in the Chicago Metropolitan Area between DuPage Regional Airport and John H. Stroger Hospital Helipad is shown and discussed. Furthermore, aggregate analysis of 434 UAM trips in Chicago Metropolitan Area between Regional Airports, between Regional and Heliports, and between Heliports is performed, along with sensitivity studies involving wind and turn control restrictions. The results discuss variations in Cruise Altitude Floor, Flight Time, and Energy Consumption of these trips using an eVTOL vehicle.</p>