Dalbergia sissoo is a multipurpose tree legume from the Indian subcontinent. Besides its extensive use as timber, the tree is also valued for its medicinal properties, leading to its widespread use in agroforestry plantations. The tree exhibits a natural tendency to thrive under diverse habitat conditions, hence exhibiting exemplary adaptive potential to environmental factors. It is easy to grow and can be propagated effectively through seeds as well as cuttings. Studies have demonstrated it as a preferential outbreeder and seed formation is essentially pollinator-dependent, and honeybees are the most effective pollinators. Self-compatibility permits selfing, largely through geitonogamy, allowing it to have dual advantages of outcrossing while ascertaining reproductive assurance through selfing under adverse circumstances. The pods with seeds ranging from one to five act as diaspore, and their dispersal occurs predominantly through wind and to some extent, by water. The pattern of packaging of the seeds within a pod seems to significantly influence the dispersal efficacy in nature. The period from the deposition of mature seeds into the soil or water to their establishment as seedlings is crucial for recruitment success in nature. Vital factors like soil moisture, community structure, prevailing habitat conditions, genetic fitness of the seeds, and interactions with beneficial organisms play a crucial role in seed germination, seedling establishment, and survivability of the species. The current chapter presents an insight into the reproductive biology of the tree species covering aspects of phenology, pollination, breeding system, and mechanism of natural recruitment in D. sissoo. These reproductive attributes make the foundation for an effective propagation strategy, genetic improvement, and conservation of the tree species.