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Angiosperm pollen, the male gametophyte, plays a crucial role in facilitating fertilization by protecting and transporting male sperm cells to the female pistil. Despite their seemingly simple structure, pollen grains undergo intricate development to produce viable sperm cells capable of fertilizing the egg cell. Factors such as resource limitation and plant aging can disrupt normal pollen development and affect pollen performance. We investigated the influence of plant resources and aging on pollen developmental failure in Azorella nivalis Phil., an exceptionally long-lived high-Andean species that grows in a stressful alpine environment. Leveraging the modular nature of plants, we aimed to identify intra-individual sources of variation in pollen developmental failure. By using pollen viability and variation in viable pollen grain size as indicators of pollen developmental performance, we assessed whether proxies of plant resource availability and aging influenced these pollen traits at the inter-individual, inter-flower and intra-flower levels. Our findings revealed decreased pollen viability in putative resource-depleted flowers and in shoots that experienced higher levels of meristematic divisions from the zygote (i.e., greater cell depth). Additionally, we observed increased variability in the size of viable pollen grains in resource-depleted anthers. Our study suggests that resource availability and shoot aging are critical determinants shaping pollen development in long-lived plants at the intra-individual level. These findings contribute to our understanding of how differences in male fitness can arise in plants, with implications for their evolutionary trajectory., (© 2024 Wiley‐VCH GmbH. Published by John Wiley & Sons Ltd.)