As the deadline for the establishment of the ASEAN Community to 2025 is approaching, the association attaches increasing importance to the digital dimension of the ASEAN Economic Community (AEC). Arguably, the ASEAN is far from fulfilling its goals, mostly, in regard to making Southeast Asia a unified manufacturing and doing business area. Concerning the association’s plans to provide intra-ASEAN cooperation with digital support, many obstacles remain in place. In these circumstances, much will depend upon the “down-top” vector. Specifically, Southeast Asian industry and business champions, among which the company Singapore Airlines figures prominently, can lead by example. The article scrutinizes the measures implemented by the Sin-gapore Airlines to digitalize its business activity with an emphasis on the COVID-19 pandemic period and distinguished fundamental factors behind their success. The author argues that although the experience of the Singapore Airlines is an individual example rather than a general pattern of business activity in Southeast Asia, regional companies will be increasingly introducing similar practices, or at least their major components, in the years to come.