Ananda and his older brother, Devadatta, who would become infamous for his attempts to disrupt the Sangha and for his many assaults on the Buddha, were among the six young Shakya nobles who, with the barber Upali, requested permission to join the Sangha. Although Upali and the others were ordained immediately, Ananda and Devadatta were not permitted to be ordained.

One scripture offers the following account of how Upali overcame his lowly birth to become one of the Buddha's disciples. When Shakyamuni was a hermit in an earlier existence, he once asked the palace barber to shave his head, but the barber refused contemptuously because of the hermit's wretched appearance. The barber's nephew, who was an inexperienced novice, condemned his uncle's unkindness and did his best to shave the hermit.

One day, observing workers in his family's fields, he saw how the spade turned up earth teeming with white insects, which were crushed to death in the next instant by blows of the hoe. He observed the farmers whipping groaning oxen forced to pull heavy loads. Through these images, Maha-Kassapa came to understand the transience of life and the great suffering required to support his life of luxury.