An important, contemporary focus of scholarship is on the necessary structural conditions to promote a sustainable transition in agriculture. This study examines the possible role of anti-systemic structures, delinked and exilic, in conditioning transitions to agroecological production. I conduct a comparative-historical analysis of two periods, 1959–1991 and 1992–2016, within a single case, Cuba. The results provide evidence that the prevalence of delinking with incorporation maintains an industrial model of agricultural production, even while bringing the law of value under sovereign control. In this way, the existence of delinking as one type of anti-systemic structure is not a sufficient condition for increasing agroecological production; although data suggests that delinking can provide important tools to support sustainable transitions in future periods. In the second period characterized by increasing prevalence of an exilic structure in conjunction with delinking, results demonstrate that anti-systemic structures operate complementary to one another and can maintain partial incorporation while increasing the application of agroecological production. As such, this study provides a rationale for future research and action on anti-systemic structural mixture conditioning sustainable transitions.