In the turbulent years before World War II, U.S. strategic planners struggled with the question of Canadian security. Franklin Roosevelt took a unique interest in America’s northern neighbor and persistently encouraged Canada to do more to ensure its own defense especially through alliance with the U.S. This aspect of foreign policy resulted in a delicate balancing act between U.S. officials who sought to downplay the strategic importance of Canada and Canadian leaders who saw American overtures as a threat to Canadian sovereignty. The first chapter discusses Roosevelt’s early efforts between 1933 and 1937 to increase Canadian interest in North American defense. The second follows events up to the outbreak of war. Although Canada had been seen as part of the rival British Empire. Canada now became a natural ally in hemispheric security efforts. Roosevelt’s dealings with Canadian Prime Minister W.L.M. King, who would be branded a puppet for these interactions, and the evolution of continental defense efforts are discusses in the third chapter. The final chapter chronicles the wartime struggles of two new allies, as Roosevelt became more concerned with Europe and the coming Soviet threat.