This paper examines the adequacy of current AirLand Battle doctrine in assisting the operational commander in making his decision on when to counterattack at the operational level against Warsaw Pact forces in a war in Central Europe. It provides a comparative analysis of current doctrine with the historical experience of Field Marshall Erich von Manstein during his winter campaign in southern Russia and the Ukraine when he counterattacked against the Soviets'; Operations STAR and GALLOP in February and March, 1943. It identifies specific considerations of Manstein, assesses how they affected the outcome of the campaign, and examines their implications for the US Army as it continues to develop its own operational doctrine and style. The conclusion of the study is that while the doctrine in FM 100-5 is not wholly supported by Manstein's experience, it does reflect the interdependent relationship of the myriad conditions of warfare. Manstein understood the conceptual relationships although he considered certain factors that FM 100-5 does not specifically relate to timing. The most important implication of his experience, however, is that understanding the three fundamental issues which FM 100-5 identifies as constituting operational art is essential to making decisions on timing of operational-level counterattacks.