This chapter outlines Estonian translations of Milton’s works and their socio-cultural context in order to reveal the translators as writers keenly aware of the value of their translations as weapons of communication trained on their environment. All three translations—the prose translation of Paradise Lost and Paradise Regained in 1895, the verse translation of the beginning of book 3 of Paradise Lost in 1962, and the 1974 translation of Areopagitica—were done under the circumstance of censorship practised in Estonia by either Russian or Soviet authorities. The 1895 translation was read in an atmosphere of late national awakening when Estonians were trying to find a way to restore their ‘paradise’ of independence. The 1962 verse translation was published in the hope of consciously influencing the moral attitude of its readers. The 1974 translation of Areopagitica highlighted the absurdities of Soviet book production.