This chapter, The Life & Inquisition of Abba Estifanos, focuses upon the medieval contentions between the Emperor Zara Yacob and the founder of the Monastic Order of Daqiqa Estifanos, Abba Estifanos. The fifteenth-century debate between Negus Zara Yacob and Abba Estifanos is fundamental to understanding the unique Trinitarian theology contained within The Ge’ez Book of the Trinity. By considering the historical epoch which produced the manuscript, we better understand the tremendous effort invested in preserving this living homily. We better understand the perseverance of the Monastic Order during the times of tumult for the Ethiopian Empire, which followed the exile of the Estifanites and the martyrdom of Abba Estifanos.