Sustainability has been an area of growing importance in the transportation field over the past two decades. In the United States, the Federal Highway Administration (FHWA) now provides an online tool that allows agencies to assess their performance in transportation design and operations, and include examples of how agencies have made use of the checklist based tool that the FHWA provides. The challenge for agencies charged with winter maintenance is that tools such as provided by FHWA are very general in nature. Winter service operations are only one area (comprising four items) among many covered by the FHWA tool. For an agency wishing to conduct an indepth investigation of the sustainability of their winter service operation, the FHWA tool is too coarse. This is not a criticism of this tool but rather an acknowledgement of the scale of use for which it is intended. This means that to conduct an in-depth investigation of winter service operations and their sustainability, an agency must to some extent revert to first principles of sustainability. Such first principles might be expressed as: “Sustainable development meets the needs of the present without compromising the ability of future generations to meet their own needs.”