Experiments were conducted to evaluate the promise of Tinnevelly senna, Cassia angustifolia Vahl, as an alternative crop for stressful agroecosystems. Effects of drought, foliar nitrogen application and crop type on sennoside yields were studied with simultaneous measurements of net photosynthesis. Short term drought increased sennoside A + B concentration (% dw). After drought-induced morphological changes had occurred, long term drought did not influence sennoside A + B concentration but severe loss of leaf biomass caused 78% reduction of the sennoside yield per plant. Foliar nitrogen application increased the total sennoside A + B content per plant by 140% when the plants were not water stressed, but in severely droughted plants, no effect of foliar nitrogen application was detected. Although foliar nitrogen application increased sennoside A + B per plant, the sennoside concentration (% dw) decreased. The latter effect was still persistent three months after the nitrogen treatments were discontinued. In a comparison among three crop types of Tinnevelly senna, ratoon plants had the highest sennoside A + B concentration in leaves followed by seedlings and cuttings. However, seedlings produced the highest sennoside A + B yield per plant due to the higher leaf biomass. Except in long term drought, sennoside levels were higher in leaves with lower net photosynthesis, and were increased by treatments that induced physiological stress. Lower net photosynthesis occurred in short term and long term drought, and with deprivation of foliar nitrogen supplement. In contrast, sennoside yields per plant are readily increased by treatments that increase the total leaf biomass. Short term drought, nitrogen stress and ratooning are promising component technologies for field and on-farm investigations with the goal of increasing sennoside yields.