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This study attempts to analyze the decisions made by Field Marshal Albert Kesselring prior to and during the battle of Anzio in February 1944. The focus of the investigation is on Kesselring’s decision to shift Army Group reserves from the Rome area prior to the Allied amphibious assault at Anzio on 18 January 1944, then his involvement in the development and execution of the German counterattack against the Allied beachhead conducted on 16 February 1944. The investigation reveals that Kesselring, the Army Group commander, made a proper and effective decision in committing the Army Group reserves to the German defensive line prior to the invasion, and that his involvement in the development and execution of the German counterattack at Anzio was doctrinally sound and generally effective.