Fouling of oil-exposed surfaces remains a crucial issue due to the continued importance of oil as the world’s primary energy source. The key perpetrators in crude oil fouling have been identified as asphaltenes, a poorly-described mixture of diverse polyfunctional molecules that form part of the heaviest fractions of oil. Asphaltenes are responsible for a decrease in oil production and energy efficiency, and an increase in the risk of environmental hazards. Hence, understanding and managing systems that are prone to fouling is of great value but constitutes a challenge due to their complexity. In an effort to reduce that complexity, a study of a synthesised foulant of archipelago structure is presented. An alternative perspective on previously described solubility and aggregation mechanisms (eg. Critical Nanoaggrerate Concentration, Critical Clustering Concentration) is offered since the characterised system favours a continuous distribution of n-mers instead. A battery of experimental and modelling techniques have been employed to link the bulk and interfacial behaviour of a representative foulant monomer to effective fouling mitigation strategies. This systematic approach defines a new multiscale methodology in the investigation of fouling systems.