In this study we performed a comparative analysis of the evolution of the system of trade licenses in Bessarabia (a Romanian territory under Russian rule since 1812) and Romania (1859-1914). Based on researched data, we can ascertain that the system of commercial licenses in Bessarabia and the Romanian Principalities, introduced almost simultaneously in 1831, experienced a somewhat similar development until 1863, when it was reformed, as well, practically simultaneously. However, the implementation of a truncated reform in the Russian Empire, with some reactionary reminiscences, led to a radical rupture between the two systems, to the detriment of Bessarabia. As a result, progress in the development of the trade sphere was quite modest, and the territory between the Prut and the Dniester felt the full myopia of the tsarist authorities, who aimed at the immediate but illusory increase of tax revenues, to the detriment of a sustainable growth in long-term perspective. This handicap was remedied only after 35 years, in 1898, finding Bessarabia at the beginning of the twentieth century in a chronic delay in terms of the stage of development of economic processes, compared to over the Prut territories.