Sugar was one of the most commercially successful productions during the first phase of the Portuguese expansion. From the second half of the fifteenth century, the high economic profits achieved in the Madeira Island were followed by less satisfactory experiments in the Azores and Cape Verde archipelagos. On the contrary, in the first decades of the sixteenth century, the production of sugar in São Tomé was successful, being greatly supported by the large-scale use of African enslaved labour. This study involved analysing sugar moulds found in archaeological contexts on the islands of Madeira, Santiago, and São Tomé, considering their technological and typological aspects. Selected fragments were macroscopically described to identify each fabric, using archaeometric data when available and relevant. These ceramics were also drawn to establish respective morphologies, and all impressed or incised marks were registered as they convey important characteristics of the fabrics and their production centres. At the same time, we suggested a typology of sugar moulds, considering their volumetric analysis, while relating it to known historical evidence that highlight the role of royal control and the pursue of high-quality sugar. The paper also reflects on which supply routes were most important for such vessels going to the sugar-producing islands, from the end of the fifteenth to the beginning of the seventeenth century. This approach opens up new lines of research concerning the commercial interactions around the sugar economy in this first globalization.