The 2020 report Tax Administration 3.0: The Digital Transformation of Tax Administration identified the automated connection of systems between tax administrations and business as one as one of core building blocks of seamless tax administration. This report, Tax Administration 3.0 and Connecting with Natural System: Initial Findings, explores this issue in the context of sharing and gig economy platforms and identifies the key questions for businesses and tax administrations to consider. It also lays the ground work for future collaboration by identifying a possible technical framework to support these connections. This report was developed by officials from Australia, Canada, Denmark, Ireland, Israel, Finland, the United Kingdom, and supported by the Secretariat of the OECD’s Forum on Tax Administration.