Zeng Jinglai was one of few significant figures in Taiwan who received a modern Buddhist higher education during the Japanese occupation period and into the early post-war period. With his deep learning and cultivation of Buddhism, abundant life experiences, and skill in responding to social circumstances, he was able to play the role of a "boundary crosser" in the history of Taiwanese Buddhism. The term "boundary crosser" used in this article refers to several aspects: 1) era and nationality: Chinese Buddhism vs. Japanese Buddhism; 2) his identity as a religious master: master of monks vs. laymen; 3) beliefs and attitudes: orthodox beliefs vs. superstition; 4) activities and operations: innovation vs conservatism. Zeng Jinglai has become a representative "boundary crosser" in the history of Buddhism in Taiwan. His life and experiences can be examined from two perspectives: personal conditions and religious environment. With regard to the former, Zeng Jinglai received a Japanese Buddhist education in his youth, gradually became a Taiwanese native elite Buddhist figure, and cooperated with the Japanese authorities to promote religious reforms. In his middle ages, he also played the role of a local Buddhist elite and cooperated with the national government to carry out the "Sinicization" project of Buddhism. The latter perspective acknowledges that Taiwan's religious environment has always had highly permeable boundaries. Whether it was Buddhism, popular sects, or folk beliefs and practices, mutual interactions and connections between religious groups were already the norm among the populace during Zeng's life. These conditions offered a natural environment to foster Zeng Jinglai's "boundary crossing."