In 1848, Habsburg Trieste became the target of German nationalists gathered in Frankfurt. The Frankfurt parliament, born out of the revolutions of 1848, has been widely depicted as a liberal experience. Yet its nationalist stances, which included the creation of a unitary German state through the absorption of vast multiethnic regions of the Habsburg monarchy, whose Austrian crownlands were part of the German Confederation, bear witness to the illiberal nature of the Frankfurt parenthesis of 1848–1849. Notwithstanding the assimilatory tendencies of the Frankfurt parliament, Italian activists in Trieste supported the inclusion of the Habsburg port in an enlarged Germany, hoping to break away from Habsburg rule, which they portrayed as oppressive. This article argues that the contradictory Italian support for the German Confederation highlights the paradoxes at the basis of nationalist movements at their onset, while also pointing to the difficulty that nation-states would soon witness in dealing with other ethnic groups within their borders. On the contrary, it was the Habsburg monarchy that, in its centuries-long tradition of accommodating different ethnicities into its fold, represented what to present-day observers comes closer to political liberalism than the so-called liberal national parties that opposed Habsburg rule.