This study investigates the axial pull-out behavior of a historical iron tie rod anchorage system, focusing on the potential type used in the 19th-century Panagia Faneromeni church in Nicosia, Cyprus. Scaled specimens made from Gerolakkos stone and steel were subjected to axial pull-out tests to simulate seismic forces. The study examines failure mechanisms, stress distribution, and the impact of anchorage system design on the tie rods’ performance under loading. Results reveal that specimens primarily failed due to transverse and longitudinal cracking, especially in areas of high stress concentration, such as the contact surfaces between the anchorage device and the stone. The role of the confinement provided by the experimental setup in enhancing anchorage resistance is highlighted, as it promotes a more ductile response and prevents premature slippage. This finding suggests that external confinement strategies could be employed to improve the seismic resilience of historical anchorage systems. The research underscores the need for further investigation into concealed anchorage systems, which are often omitted in structural vulnerability assessments, to better inform conservation efforts and retrofitting strategies for heritage buildings.