This Working Paper seeks to analyse the 2006-07 Crisis in Dili through the lens of the urban tipping process of violent conflict. The conceptual framework of this project furthers our understanding of how different aspects of the urban environment are interrelated, and acts as a guide to the organised complexity of the city. In the case study of Dili, the notion of the “tipping point” is used to generate new insights about the Crisis and to question popular narratives, both domestically and internationally, about the role of the security sector and organised youths in the collective violence that marked it. The participatory research conducted in 2011 uncovered a number of common themes that interlocutors identified as underlying recent events in Dili: these include the discrepancy between traditional forms of authority and the values of liberal democracy, the discursive role of the “east-west” divide, the presence of martial arts, ritual arts and other youth groups on both the city and sub-city levels, the importance of past conflicts and disputes among the political elite in shaping conflict in present-day Timor-Leste, and the on-going stand-off and competition in the formal security sector. Along these themes, the Working Paper offers a synthetic account of the environment in which the petitioner issue within the armed forces came to tip into collective urban violence in 2006. According to the findings, and as elaborated in the adjoining Policy Brief, it may be worthwhile to consider Dili as a genuinely urban space with its own particular security dynamics, competing political and ritual authorities, acute land insecurity, and specific planning needs.