Winter wheat, the primary grain grown in Switzerland plays a crucial role for domestic food security. It is typically harvested in July and early August, roughly coinciding with the peak of the hail season. Recent global warming has led to earlier harvest dates, thus shortening the time window during which wheat is potentially exposed to hail. At the same time, the frequency of hailstorms in Switzerland has increased. In view of these two opposing trends, the question arises as to whether the risk of hail damage to wheat has decreased or increased over the past few decades. To address this question and evaluate the relative importance of the two trends, we combined wheat phenology simulated with the World Food Studies (WOFOST) model with a reconstruction of the seasonal distribution of hail days over the periods 1972–1991 and 2002–2021. We find that across Switzerland, harvest dates advanced by an average of 13.4 days between 1972–1991 and 2002–2021, while the mean number of hail days during wheat’s growing season increased from 0.79 to 1.12. Thus, while early harvests have potentially reduced hail risk by 13%, the significant 55% increase in hail frequency has offset this benefit, resulting in a net 42% increase in hail risk. It is beyond doubt that efforts are needed to enhance the agricultural sector’s resilience against increasing hail damage risks. Our findings emphasize the importance of quantitative assessments that combine the development of hail scenarios, on the one hand, and crop growth modeling, on the other.