This paper examines the recent development of two cane sugar industries, those of Barbados and Australia, and considers how and why sugar production has tended to become increasingly problematic in both of these cases. The problems of nationally based sugar industries are commonly explained by reference to the volatile and depressed state of the global sugar economy or in terms of the relative efficiency and cost competitiveness of the industries concerned. Both of these factors are considered here, but the central theme of the paper revolves around the ways in which two very different production systems have themselves generated contradictions and barriers to their own reproduction. Strategies promoted to address these contradictions have tended to be imperfect and temporary. Moreover they have also tended to involve the increasingly severe exploitation of both environmental and human resources. Insights from regulation theory are used to define a context within which events in these industries are understood as outcomes which reflect not just structural mechanisms and contingent factors, but also the processes of structuration which link these. The final section of the paper considers the significance of this analysis to wider issues such as sustainability and regulation of sugar production at both international and national scales.