In 1900 Vynnychenko joined the Revolutionary Ukrainian Party (RUP) and enrolled in the law department at Kiev University, but in 1902 or 1903 he was expelled for participation in revolutionary activities. As a member of the RUP he provided political agitation and propaganda among the Kievan workers and peasants from Poltava and was jailed for several months in Lukyanivska Prison. He managed to escape from his incarceration. In 1902 Vynnychenko published in "Kievskaya starina" his first novel "Beauty and strength", after which he became known as a writer. Afterward, due to a new arrest he was forcibly drafted into a punitive battalion in the Russian Imperial army where he began to agitate soldiers with revolutionary propaganda. Tipped off that his arrest was imminent, Vynnychenko illegally fled to eastern Galicia, Austria-Hungary. When trying to return to Russian Ukraine with revolutionary literature, Vynnychenko was arrested and jailed in Kiev for two years with a threat to spend the rest of his life in katorga. After his release in 1905, he passed his exams for a law degree in Kiev University.