Ireland’s Nine Years’ War (1594-1603) marks a crucial juncture in the development of three unique cultural identities: Gaelic Irish, Old English, and New English. But, while this war reinforced the socio-religious character of the Gaelic Irish and New English, it compelled the descendants of Ireland’s twelfth-century Anglo-Norman conquerors, known collectively as the Old English, to reappraise their status as Irish-born Catholics loyal to the English Protestant establishment. Building upon my doctorate, which examined aspects of Old English identity formation within the Pale – an area roughly comprising counties Dublin, Kildare, Meath, Westmeath, and Louth – during the first stage of the Nine Years’ War (1594-1599), this project will consider the same community during the second stage of this conflict (1599-1603). This war is best studied in two phases because the April 1599 arrival of the Earl of Essex as Lord Lieutenant of Ireland coincided with a marked escalation in hostilities, an increased commitment of money and manpower from England, the resurrection of a militant Jesuit mission, and the deployment of an aggressive patriotic propaganda campaign by the Irish Catholic Confederacy. The impact of this intensification on the Old English Pale community would have been noticeable and this project will explore how escalating hostilities, clerical involvement, and the production of patriotic propaganda during the second phase of Ireland's Nine Years’ War contributed to the emergence of a distinct Old English identity by the early 1600s.