A reconstruction and critical interpretation of Heidegger's remarkable relationship to the poet Georg Trakl. Winner of the 2023 Symposium Book Award presented by Symposium: Canadian Journal of Continental Philosophy In the early 1950s, German philosopher Martin Heidegger proclaimed the Austrian expressionist Georg Trakl to be the poet of his generation and of the hidden Occident. Trakl, a guilt-ridden lyricist who died of a cocaine overdose in the early days of World War I, thus became for Heidegger a redemptive successor to Hölderlin. Drawing on Derrida's Geschlecht series and substantial archival research, Dialogue on the Threshold explores the productive and problematic tensions that pervade Heidegger's reading of Trakl and reflects more broadly on the thresholds that separate philosophy from poetry, gathering from dispersion, the same from the other, and the native from the foreigner. Ian Alexander Moore examines why Heidegger was reluctant to follow Trakl's invitation to cross these thresholds, even though his encounter with the poet did compel him to take up, in astounding ways, many underrepresented topics in his philosophical corpus such as sexual difference, pain, animality, and Christianity. A contribution not just to Heidegger and Trakl studies but also, more modestly, to the old quarrel between philosophy and poetry, Dialogue on the Threshold concludes with new translations of eighteen poems by Trakl.