While none of the Atlantic archipelagos ever acquired metropole status, they acted as outports of the leading peninsular entrepôts. This chapter conﬁrms their roles as essential elements in the monopoly. It validates their functions as indispensable staging posts on most outgoing and few incoming voyages. It starts by pinpointing their roles in the emerging colonial economy and it conﬁrms the importance of the sugar economy on the Canaries. Clear product cycles emerged on all of the islands at different times and it is conﬁrmed that the monopoly was imposed with varying intensities. Given that these islands were less easily policed and regulated by the peninsular monopoly institutions, they developed an unstable port and urban hierarchy that helped, in turn, to weaken economic conditions. Free trade left them more isolated and they developed strong trading relations with the peninsula and far weaker ones with the Americas. By contrast, the Azorean islands of Angra, Horta and São Miguel were vital stations for returning vessels, while Maderia was sometimes visited by outgoing Portuguese vessels. Like the Canaries, the Portuguese islands enjoyed early product cycle prosperity. It was short lived. The emergence of La Havana as Spain’s leading Atlantic ship marshalling centre gradually sidelined the Azorean contribution to the Spanish Carrera.