This article examines the Soviet system of territorial autonomy by studying its impact on the Jewish population of Soviet Ukraine in the 1920s. While the new Soviet state created national republics, districts, and village councils for its non-Russian nationalities, Ukraine’s Jewish population was faced with a dilemma: Ukrainian Jews lived predominantly in cities, but urban space could not be claimed for Jewish territorial autonomy because the Soviet government hoped that peasant immigration would produce a Ukrainian working class. Without an autonomous status, many Jews felt threatened by the increasing influx of Ukrainians and the spread of Ukrainian-language institutions. Offered as a consolation prize, the Soviet Yiddishization initiative failed to cater to the needs of many Jews who preferred the Russian language as a means for social mobility. Attempts to resettle urban Jews in compact agricultural colonies suitable for territorial autonomy never reached the necessary scale. In conclusion, this article argues that the incompatibility of Soviet territorial autonomy with Ukrainian Jewish needs anticipated the Soviet state’s inability to accommodate the increasingly urban, heterogeneous, transnational, multilingual, and mobile society that emerged in the postwar Soviet Union.