The founder of the monastery was a rich widow, Maria de Guzman. The tradition of the time indicated that the second son or daughter of a family would enter religious service, and the convent accepted only women from high-class Spanish families. Each nun at Santa Catalina had between one and four servants or slaves, and the nuns invited musicians to perform in the convent, gave parties and generally lived a lavish lifestyle. Each family paid a dowry at their daughter's entrance to the convent, and the dowry owed to gain the highest status, indicated by wearing a black veil, was 2,400 silver coins, equivalent to US$50,000 today. The nuns were also required to bring 25 listed items, including a statue, a painting, a lamp and clothes. The wealthiest nuns may have brought fine English china and silk curtains and rugs. Although it was possible for poorer nuns to enter the convent without paying a dowry, it can be seen from the cells that most of the nuns were very wealthy.
In 1871 Sister Josefa Cadena, a strict Dominican nun, was sent by Pope Pius IX to reform the monastery. She sent the rich dowries back to Europe, and freed all the servants and slaves, giving them the choice of remaining as nuns or leaving. In addition to the stories of outrageous wealth, there are tales of nuns becoming pregnant, and amazingly of the skeleton of a baby being discovered encased in a wall. This, in fact, did not happen in Santa Catalina, and there are rumours of the same story in the nearby Santa Rosa convent, as well.
The convent once housed approximately 450 people (about a third of them nuns and the rest servants) in a cloistered community. It was opened to the public in 1970, when the nuns opened their doors to tourism to pay for the installation of electricity and running water, as required by law.