This study discusses the processes of increasing social malaise and an “oppositional mood” in the Cape Verdean island of Santo Antão, where growing frustration between 1975 and 1990 led to the building of massive political opposition against the single-party regime in the archipelago. Early scrutiny of the shortcomings of independent administration, anger about the installation of a new police force, resettlement schemes, a failed agrarian reform, regime violence to achieve that reform, and a generalised mood of decline in the second half of the 1980s, constitute different elements explaining the unrest in that island. Based on newly available, local archives as an innovative source, the interpretation of a remote Cape Verdean opposition island also addresses the potential of studying opposition against “winning parties” and regimes after independence in wider regional frameworks, referring to discontent and “oppositional mood” elsewhere in postcolonial (Lusophone) Africa.