AbstractUnderstanding and representing the transformation of agricultural production systems has attracted increasing interest due to its importance for identifying drivers of changes and coping mechanisms in response to global challenges. These challenges are all the most pressing in North African countries exposed to a dramatic reduction in rainfall and increasing temperatures that affect sustainability in more than half of this semi-arid territory. This paper describes an improved way to understand such transformations through a cross-cutting analysis of crop–livestock system indicators over a period of 10 years in one community in Southern Tunisia. Our methodology is divided into four steps: (i) systems identification, (ii) indicator-based assessment of system crop–livestock sustainability, (iii) hierarchical clustering to identify sustainable intensification (SI)-based farm types and, finally, (iv) analysis of trajectories of these farm types. Results showed that the sustainability of the systems studied increasingly depends on diversification rather than intensification, which dominated in the 2000s. However, diversification has not necessarily improved socio-economic viability. Over the 10-year period, results revealed a dramatic increase of almost 50% in the population of small-scale farms whose viability depends on a range of on- and off-farm activities to meet the short-term needs that correspond to a buffer strategy. Additionally, the dominant SI processes were shown to be mostly based on diversification to livestock activities with both milking and fattening. Our holistic and timeline approach to system transformation makes it possible to account for sustainability between (systems) generations, which will be highly needed in future discussions about sustainability.