Agroclimatic variables may affect insect and plant phenology, with unpredictable effects on pest populations and crop losses. Bactrocera oleae Rossi (Diptera: Tephritidae) is a specific pest of Olea europaea plants that can cause annual economic losses of more than one billion US dollars in the Mediterranean region. In this study, we aimed at understanding the effect of olive tree phenology and other agroclimatic variables on B. oleae infestation dynamics in the Umbria region (Central Italy). Analyses were carried out on B. oleae infestation data collected in 79 olive groves during a 7-year period (from 2015 to 2021). In July-August, B. oleae infestation (1% attack) was negatively affected by altitude and spring mean daily temperatures and positively by higher winter mean daily temperatures and olive tree cumulative degree days. In September-October, infestation was negatively affected by a positive soil water balance and high spring temperatures. High altitude and cumulative plant degree days were related to delayed attacks. In contrast, high winter and spring temperatures accelerated them. Our results could be helpful for the development of predictive models and for increasing the reliability of decision support systems currently used in olive orchards.