The city was seized by Philip V, King of Macedonia, in 200 BC, and remained under Macedonian control until the conclusion of the Second Macedonian War in 196 with the Peace of Flamininus, which proclaimed Sestos a free city. In 196 BC, during the Roman–Seleucid War, Sestos surrendered to Antiochus III, "Megas Basileus" of the Seleucid Empire, who refortified the city in 191 in preparation for a Roman attack, only for the city to surrender to Gaius Livius Salinator in 190. At the end of the war, the Treaty of Apamea of 188 awarded Sestos to the Kingdom of Pergamon. By the end of the Hellenistic period, the offices of "gymnasiarch" and of "ephebarch", with responsibility for the "neoi" (young) and "epheboi" (adolescents), are attested at Sestos.