A new examination of the Aleutian-Midway campaign provides fresh lessons about the challenges of operational planning both then and now. The insights provided by contemporary operational art and design were used to reinterpret the campaign. U.S. concepts dealing with operational art and operational design provide a list of planning factors that point to the errors the Japanese made during operational planning. The type of errors made along with the historical evidence of Japanese actions provided a basis for assessing the cultural, organizational, and leadership factors that prevented more effective planning and a more successful operation. Additionally, applying modern aspects of campaign planning led to fresh lessons about the challenges of planning both then and now. Providing a contemporary understanding of the compounding effects of such complexities help illuminate key aspects of operational art.