The present study aims at sketching the history of the first 20 years of the Salesian Orphanage of Macao (the “Orfanato”), focusing mainly on three problem areas of the first Salesian settlement in China: 1. the charismatic urge that brought the Salesians to Macao; 2. the first painful impact with reality; 3. the role played by the Orfanato in the overall strategy of Salesian expansion.