Climate change-induced variations in temperature and precipitation negatively impact plant growth and development. To ensure future food quality and availability, a critical need exists to identify morphological and physiological responses that confer drought tolerance in agro-economically important crop plants throughout all growth stages. In this study, two Sorghum bicolor accessions that differ in their pre-flowering responses to drought were exposed to repeated cycles of drying and rewatering. Morphological, physiological, and histological traits were measured across both juvenile and adult developmental stages. Our results demonstrate that plant height is not predictive of metaxylem area but does influence the hydraulic path and water management in an accession-specific manner. Further, when drought-responsive changes to the plant architecture are unable to compensate for the hydraulic risk associated with prolonged drought exposure, tight control of stomatal aperture is crucial to further mitigate hydraulic damage and prevent xylem embolism.