The late 15th and early 16th centuries saw a revival of the medieval preoccupation with the conversion of prostitutes. Not only had the number of prostitutes increased, but also the appearance of the disease of syphilis in the late 15th century made them a threat to public health, and interest was renewed in creating institutions to contain them.
For example, a convent for converted prostitutes, known as the Convertite della Maddalena, was established in Rome on 19 May 1520 by Leo X. The convent was founded, financed, and operated by members of the Arciconfraternita della Carità (the archiconfraternitas charitatis), a charitable sodality founded the previous year, 1519, by Cardinal Giulio de' Medici, the future Clement VII and Leo X's cousin, and confirmed by Leo X with a papal bull in 28 January 1520.
Many such convents had been founded across Europe as part of the church's ongoing mission to reform prostitutes. As early as 1198 Pope Innocent III had issued a decree urging Christians to aid the "conversion" of former prostitutes and even offered remission of sins to men who married prostitutes to reform them. Already in the 12th century, if not earlier, public and private benefactors in Germany, France, Italy and elsewhere in Europe had founded monasteries and residential institutions where reformed prostitutes were expected to dedicate themselves to a secluded penitential life. Similar communities were being established in Germany.
Convents for converted prostitutes had been established earlier in Byzantium, notably the Metanoia ("Repentance") founded by Theodora, the wife of Emperor Justinian, and a similar establishment by Emperor Michael IV (1034-41).
In recognition and support of these efforts, in the early thirteenth century the papacy turned its attention to creating a special religious order of penitential nuns to serve as a shelter for reformed prostitutes. Around 1225, Rudolf of Worms founded the Order of the Penitents of St. Mary Magdalen to which Pope Gregory IX gave ecclesiastical sanction through the granting of certain dispensations and privileges in the papal bull Religiosam vitam eligentibus on 10 June 1227.
In 1232 Gregory placed the order under the rule of the Augustinian friars, which was confirmed in 1248 by Innocent IV. The first convents of this new order were founded in Germany and others followed in Italy and France. Communities of repentant prostitutes were founded in several cities in Italy in the thirteenth century, including Rome, where in 1255 Pope Alexander IV ordered Giovanni da Toledo, Cardinal of San Lorenzo in Lucina, to establish a refuge for convertite in the church of S. Maria sopra Minerva.
In 1257 in Florence a group of reformed or converted prostitutes was established in Santa Maria Maddalena Penitente on what is now Borgo Pinti. In 1669 the convent was rededicated as Sta Maria Maddalena dei Pazzi. Convents were also opened in France in Marseilles in 1272, in Avignon sometime before 1293, and in Toulouse in 1294. Later, elsewhere, besides Rome in 1520, convents were opened in Naples (1324), in Paris (1492), Seville (1550), Rouen and Bordeaux (1618). Similar institutions were founded in many smaller towns and cities across Europe.
As she had been since the thirteenth century, Mary Magdalen was upheld as the example for the converted prostitute to follow. However, whereas in the thirteenth century Mary Magdalen was promoted as the paradigm of penance, in the 15th century more emphasis was placed on her conversion and her life prior to that. This is most noticeable in the plays and liturgical dramas of the period. As early as the 10th century Mary Magdalen had been appearing in the "Whom do you seek?" (Quem quaeritis) plays performed as part of the Easter liturgy in which she figured prominently in the story of the visit to the tomb. In the 13th century her character and role were significantly expanded to incorporate details of her life as a prostitute and her subsequent conversion and repentance.