John Syng Dorsey (1783-1818) was a Philadelphia surgeon and the author of The Elements of Surgery (1813), the first American textbook of surgery. He was also the author of Poems, 1805-1818 (UPenn Ms. Coll. 251), a forty-page collection that reveals his interests in spirituality, the history of science and medicine, and classical and eighteenth-century British poetry. Decades after Dorsey’s death, his son Robert Ralston Dorsey (1808-1869) revised his father’s poems, identified classical sources with Latin and Italian quotations, and completed Dorsey’s final, unfinished poem. This project analyzes Dorsey’s literary, scientific, and biblical allusions and contextualizes his Poems within early nineteenth-century literary history and Romantic science and medicine. This article is an expanded version of the annotated transcription and critical introduction published as “Religion, Writing, and Romantic Science in John Syng Dorsey’s Poems, 1805-1818” in Volume 1 (Fall/Winter 2017/18) of Journal of the Penn Manuscript Collective. Corrections to the original transcription, as well as the discovery of four pages of riddles at the back of the volume, reveal additional literary and theological allusions, information about the involvement of Dorsey’s wife’s family and his medical colleagues in Philadelphia charitable organizations, and Dorsey’s connections to elite early nineteenth-century Philadelphia society. The expanded introduction and annotations analyze this new evidence and discuss the five poems from Ms. Coll. 251 and eleven poems not included in the manuscript that Dorsey published in the Port Folio, an influential Philadelphia literary journal.