During June 1941, Nazi forces occupied Estonia. By 1944, when the Soviet-Nazi frontline was drawing towards the Estonian border from the East, Alfred Käärmann was conscripted into the German military. By September 1944 the Red Army had again occupied Estonia. Alfred was forced to make a decision: whether to stay in Estonia or retreat with the Germans. He chose the former, However he risked arrest and deportation by the Soviets.