Largely and critically dependent on tourism, the Dutch Caribbean subnational island jurisdictions (SNIJs) of Aruba, Curaçao and Sint Maarten turned to the Kingdom Government for cash flow support, as a consequence to the shortfall in tourist arrivals in the wake of the COVID-19 pandemic. With an already underperforming and malfunctioning political relationship with their sole shelter provider (due to the tight fiscal budgetary supervision) Aruba, Curaçao and Sint Maarten received conditions that were perceived as economic and political intrusion. These new conditions invite a thorough economic redesign in the wake of unprecedented economic conditions, new governance mechanisms and an overall decrease of welfare. Dutch Caribbean SNIJs have the opportunity to turn increasingly to a digital transformation of public services, promotion of virtual business services, and their creative sectors to circumvent the crisis. This paper highlights the calls for reform and underlines the challenges that SNIJs face in adequately addressing economic opportunities in the 21st century by tackling technological gaps that currently discourage businesses and enable a departure from economic shelter currently limiting the islands’ economies. ; peer-reviewed