Traditional farming landscapes in South and Central Portugal, known as montados, are affected by global socio-economic and biophysical pressures, putting the sustainability of the systems in jeopardy. Cork oak trees (Quercus suber L.) are characteristic features of these complex agro-silvo-pastoral agroforestry systems, delivering a globally important product, cork. The increasingly distant, global scale of decision making and trade can consequently be observed on the local, landscape, scale. In this study, we use a value chain approach to test the concept that landscape products can ensure sustainable management of the landscape of origin. We interviewed agents—cork producers, intermediaries, industrial transformers, and winemakers—about the challenges they perceived in the business and how these were connected to the landscape of origin. We illustrate the network of agents and sub-actors involved in the sector and highlight the most prominent concerns. We conclude that this approach can reveal the major points for determining the future of the montado, and we suggest that collaboration amongst value chain agents can be a pathway to landscape sustainability.