This article evaluates the extent to which the architectural organization of a Dutch plantation compound was designed to aid in plantation administrators’ and owners’ ability to engage in acts of social control via surveillance. The particular compound, Groot Walling, is located on Banda Besar, the largest of the Banda Islands, Maluku Province, Indonesia. Our initial hypothesis is that the compound was designed to aid in surveillance activity by administrators against slaves and contract workers. After discussing the history of the islands and prior historical archaeological research into surveillance, we employ GIS-based visibility analysis to evaluate this hypothesis. A series of single viewsheds were calculated within Groot Walling and compared against viewsheds generated from hypothetical organizations of that same compound. The results, while preliminary, are not consistent with our hypothesis, and we tentatively reject it. We follow up these results with some exploratory analyses, utilizing a series of total viewsheds to try to better characterize the visual properties of this compound. We then suggest some alternative hypotheses for our results, and end with a discussion of future research directions.