Globally and specifically in Africa, governments' major revenues, and the countries' peace and security, are being highly challenged by the very increasing nature of illegal and informal cross border trade. As a result, the issue of contraband is attracting both the academics and practitioners. It is with this reality that this study stood with the general objective of assessing the nature of cross-border contraband trade across the main route from Moyale (border town between Ethiopia and Kenya) to Hawassa (the capital of Ethiopian Southern region). To this end, the study has utilized exploratory and descriptive designs utilizing both primary and secondary data sources. As instruments of data collection Observation, Key informant interviews and review of organizational documents were utilized to feed the paper. In addition a total of 55 key informants were purposively targeted except contrabandists who were selected through snowball sampling. Moreover, in line with the design, a descriptive method of analyses has been utilized. Finally, the study indicated that contraband trade being carried out across the main route from Moyale to Hawasa takes different forms, and techniques of passing check points like bribing customs and security personnel, building extra hiding place (shag) in vehicles, passing stations via journeys in jungle and informal roads are most widely utilized. Moreover the dominant commodities smuggled are textile and foot wares and electronics. Hence, the authors recommend that synergy approach must be best utilized by multiple actors and concerned bodies to assess the causes and consequences of contraband trading and broader and comprehensive policy framework ought to be developed towards overcoming the problem.