That phrase, from Harold Leask's mid-twentieth-century survey of Irish churches, is not evasion; it is an accurate diagnosis. The ruins at Timoleague accumulated over so many building campaigns, repairs, and insertions that reading the fabric is less like following a timeline and more like untangling a conversation that kept changing subject. A tower was squeezed into the choir, blocking windows that were already there. Arcades were rebuilt at awkward angles. A western wall was raised flush with one range but stopped short of another by roughly forty centimetres, a gap that quietly records the moment one phase of construction ended and another had not yet begun.

The friary was established before 1316, though whether the founder was Donal Glas Mac Carthy or William de Barry remains unresolved. The east window of the church, with its three pointed lights separated by stone mullions, the central light rising slightly higher than the others, is comparable to a window in the Franciscan friary at Kilkenny and suggests a date of around 1300 for the earliest fabric. Among the more curious survivals in the choir are mural passages, narrow corridors built within the thickness of the walls, running between the north and south sides through the east wall at the height of the window embrasures; their precise function has not been conclusively explained. A later and significant phase of building is associated with Edmund de Courci, who became Bishop of Ross in 1494 and was buried in the friary in 1518; the records credit him with constructing the steeple, dormitory, infirmary, and library, which places the cloister ranges to the late fifteenth century. The cloister arcading at the north-east corner, later reconstructed by the Board of Works, resembles work at Adare friary dated between roughly 1470 and 1500, consistent with de Courci's patronage. The friary suffered considerable damage and was repaired again in 1604. Inside the sacristy, a stone with a shallow circular depression is recorded locally as a wart well, a folk-healing site of the kind occasionally found within monastic precincts, where a natural or worked hollow in stone was believed to cure skin complaints when filled with water.

The ground level inside the church is noticeably higher than it would originally have been, the result of centuries of burials accumulating beneath the floor; excavation has exposed the bases of piers in the transept and aisle that are otherwise invisible. Visitors who look carefully at the east wall of the domestic range will notice a worn carved head flanking one of the window openings, easy to pass without registering it against the general texture of the stonework.