Since at least the eighteenth century, free labour in “the West” has been contrasted with serf labour in Russia and “eastern Europe”. This paper intends to call that view into question and to show that serfdom was never officially institutionalized in Russia, and that the regulations usually invoked to justify that opinion were actually intended not to “bind” the peasantry but to identify noble estate owners, as distinct from nobles in state service or the “bourgeoisie”. However, it is a matter not only of legal definitions. This paper studies how the tsarist administration, nobles, and peasants themselves made use of courts of law in order to contest ownership titles and, on that basis, the obligations and legal status of peasants and workers. Great changes had occurred in their legal status before the official abolition of serfdom in 1861, in outcomes that were rather similar to those which had been recently achieved in the “second serfdom” in Prussia, Lithuania, and Poland. In turn, that means that such labour contracts and institutions were not the opposites of “free labour” contracts and institutions, which placed many more constraints on workers than is usually acknowledged. To prove the point, we compare tsarist regulations with the Master and Servants Acts and indenture in Britain and its Empire and with French regulations on labour, domesticity, and day labourers.