Global change has created less stable forest systems and given urgency to understanding limitations to the establishment of tree seedlings beyond current range boundaries. We quantified trends in 13 years of annual northern red oak (QURU) seedling survival data for 1733 marked individuals at a local species distribution boundary within the northern hardwood forest in New Hampshire, USA. Over the study period, the median distance of seedlings into the valley did not change, although there was a net gain of 89 plots (5 m2) occupied. For a subset of seedlings that were marked in their year of birth (N = 937), we examined relationships among terrain, vegetation community, and initial individual seedling traits, and evaluated their effects on time to seedling mortality using a parametric accelerated failure time model. The year of seedling germination had the largest effect on survival with increasing mortality rates for seedlings from more recent cohorts. Seedlings had longer survival times where oak seedling densities were lower, shrub cover was higher, and when the acorn remained attached. Additionally, survival time was increased in higher elevation plots, which were also located further into the valley. Interannual seedling survival (N = 1580) was strongly impacted by seedling condition in the previous year, particularly leaf number and amount of leaf damage. Most seedling deaths occurred over winter, and seedlings failed to break bud the following spring. Interannual variation in seasonal climate, particularly deep, heavy snowpack in 2019 followed by drought conditions in 2020, coincided with recent elevated mortality. Overall, the median survival time of 3–4 years and the rapid turnover of the oak seedling population currently limit ability for expansion, although the net gain of occupied plots and increase in survival at higher elevation plots with lower QURU densities present some mechanisms that could promote expansion if the current suboptimal understory conditions shift to favor QURU.