Reproductive organs are the main reason we grow and harvest most plant species as crops, yet they receive less attention from phenotyping due to their complexity and inaccessibility for analysis. This review highlights recent progress towards the quantitative high-throughput phenotyping of reproductive development, focusing on three impactful areas that are pivotal for plant breeding and crop production. First, we look at phenotyping phenology, summarizing the indirect and direct approaches that are available. This is essential for analysis of genotype by environment, and to enable effective management interpretation and agronomy and physiological interventions. Second, we look at pollen development and production, in addition to anther characteristics, these are critical points of vulnerability for yield loss when stress occurs before and during flowering, and are of particular interest for hybrid technology development. Third, we elaborate on phenotyping yield components, indirectly or directly during the season, with a numerical or growth related approach and post-harvest processing. Finally, we summarise the opportunities and challenges ahead for phenotyping reproductive growth and their feasibility and impact, with emphasis on plant breeding applications and targeted yield increases.