Contemporary challenges, such as climate change, the need to ensure food security for a growing population, and the demand for environmentally sustainable production systems, require progress in the development of new paradigms for agricultural management. These systems should integrate productivity, conservation of natural resources, and the resilience of agroecosystems in order to build upon the gains achieved by the conventional model and respond more effectively to the demands of the twenty-first century. Within this context, tropical regenerative agriculture has emerged as an alternative approach to addressing the environmental, social, and productive challenges associated with conventional and traditional agricultural systems. However, the concept remains heterogeneous, with limited consensus regarding its principles, metrics, and methods of implementation, particularly in tropical environments. This chapter aims to clarify the conceptual foundations of tropical regenerative agriculture by discussing its core principles, key challenges, and practical implications. In addition, it presents field experiences from a large-scale transition process conducted at the Lagoa do Sino Educational Farm of the Federal University of São Carlos (FELS/UFSCar), Buri, São Paulo, Brazil. The case study covers 166 hectares of grain production systems previously managed under conventional agricultural practices. The analysis highlights potential benefits as well as agronomic, operational, and logistical constraints associated with the transition process. By integrating conceptual discussion with scientific evidence, the chapter contributes to advancing the debate on regenerative agriculture in tropical environments.