Climate change is leading to the advancement of spring conditions, resulting in an earlier snowmelt and green‐up, with highest rates of change in highly seasonal environments, including alpine habitats. Migratory birds breeding at high elevations need to time their arrival and lay dates accurately with this advancement, but also with the annually variable spring conditions at their breeding sites, to maximize nest survival probabilities and reproductive output. Nest survival probability and mean nestling mass were analysed in relation to lay date and habitat conditions in an alpine population of the migratory Northern Wheatear Oenanthe oenanthe collected over six consecutive breeding seasons in the Western Italian Alps. This open grassland species showed the lowest nest survival probability in years with an early onset of spring conditions. Within‐season, nest survival was highest when breeding late, at lower elevations, and when grass cover and grass height were higher. Both across‐ and within‐season, severe weather conditions may indirectly lead to higher early season nest failure rates by increasing predation risk. By contrast, mean nestling mass, and thus the quality of the fledglings, was lower when breeding late. This might be driven by a mismatch with the peak in food abundance. Breeding early is thus generally advantageous in terms of chick quality in our high‐elevation population, but reproductive success is limited by the risk of nest failure that is higher in early springs and early in the season. This trade‐off between breeding early and late may thus allow Northern Wheatears to maximize fitness under highly variable spring conditions. However, climate change may cause disruption to this trade‐off, and shifts in phenology could become a threat for migratory alpine birds that might not be able to keep track of advancing spring conditions.