Since the Asian Financial Crisis of 1997 and the Global Financial Crisis of 2007, members of the Association of Southeast Asia Nations (ASEAN) have sought to strengthen ASEAN's regional economies through a digital trade project known as the ASEAN Single Window (ASW). The purpose of this case study was to explore the business strategies that multinational organizational leaders used to overcome business barriers while implementing ASEAN partnership contracts and ASW region-wide projects. This study may be unique in that, at the time of this research, there was no published study in which researchers had explored a single window for a vast, multination geographical region. Data collection was done via in-depth interviews with ASW executives, studying online ASW-related conferences, and examining relevant strategic documents. A 6-phase thematic analysis process based on methodological triangulation corroborated the data and addressed construct validity through data familiarization, generating initial coding, categorizing codes and searching for themes, breaking codes into subcategories, data reduction and defining and naming themes, and report generation. The 4 strategic themes that emerged were business models and processes, public-private partnerships, project management methodologies, and overlapping themes. The findings offer insights into ways to overcome the ASW's constraints and barriers. These strategic themes developed into a list of critical success factors and a summary list of principle business strategies and best practices. The implication for social change is a regionally collaborative trading environment providing potential economic options that not only impede the deterioration of the regional social fabric but support new opportunities such as trade liberalization and economic stability.