Revolutionary political organizations have thrived and undertaken ambitious initiatives across Latin America as left-wing governments there began challenging US imperialism and moving away from neoliberal policies. In Venezuela and Brazil particularly, already-existing movements played an active role in advancing the class struggle and implementing or radicalizing socialist policies, such as the agrarian reform. In doing so, they have also established a deep but uneasy partnership with the left-wing ruling parties. This dissertation uses the framework of insurgent planning to analyse how the CRBZ and the MST, from Venezuela and Brazil respectively, are navigating through rebellious practices and engagement with the state to steer forward a revolutionary process for social transformation. It was written based on a literature review and a field investigation conducted in South West Venezuela in 2013.