Reflection cracking in asphalt concrete (AC) overlays is a common form of pavement deterioration that occurs when underlying cracks and joints in the pavement structure propagate through an overlay due to thermal and traffic-induced movement, ultimately degrading the pavement’s lifespan and performance. This study aims to determine how alterations in overlay thickness and temperature conditions, the incorporation of chopped fibers, and the use of geotextiles influence the overlay’s capacity to postpone the occurrence of reflection cracking. To achieve the above objective, a total of 36 prism specimens were prepared and tested using an overlay testing machine (OTM). The variables considered in this study were the thickness of the overlay (40, 50, and 60 mm), temperature (20, 30, and 40 °C), mix type (reference mix and mix modified with 10% chopped fibers by weight of asphalt cement), and the inclusion of geotextile fabric at two positions (one-third of the depth from the base and at the bottom). The research outcomes revealed that a decreased temperature and thicker overlay led to a higher resistance to crack initiation and full propagation, as indicated by the values of critical fracture energy (Gc) and crack progression rate (CPR). Furthermore, the study observed the enhanced crack resistance of overlays in the presence of geotextiles, whether at the bottom or one-third of the depth from the bottom, with superior performance of the former. Despite a slight enhancement in certain properties, the incorporation of chopped fibers in the overlays did not substantially improve the overall performance compared to the reference specimens. Overall, the study provides valuable insights into the variables that influence the ability of AC overlays to mitigate reflection cracking. These findings will aid engineers and designers in making informed decisions regarding overlay design and construction.