Digitalization is globally transforming the world with profound implications. It has enormous potential to foster progress toward sustainability. However, in its current form, digitalization also continues to enable and encourage practices with numerous unsustainable impacts affecting our environment, ingraining inequality, and degrading quality of life. There is an urgent need to identify such multifaceted impacts holistically. Impact assessment of digital interventions (DIs) leading to digitalization is essential specifically for Sustainable Development Goals (SDGs). Action is required to understand the pursuit of short-term gains toward achieving long-term value-driven sustainable development. We need to understand the impact of DIs on various actors and in diverse contexts. A holistic understanding of the impact will help us align the visions of sustainable development and identify potential measures to mitigate negative short and long-term impacts. The recently developed digitainability assessment framework (DAF) unveils the impact of DIs with an in-depth context-aware assessment and offers an evidence-based impact profile of SDGs at the indicator level. This paper demonstrates how DAF can be instrumental in guiding participatory action for the implementation of digitainability practices. This paper summarizes the insights developed during the Digitainable Spring School 2022 (DSS) on “Sustainability with Digitalization and Artificial Intelligence,” one of whose goals was to operationalize the DAF as a tool in the participatory action process with collaboration and active involvement of diverse professionals in the field of digitalization and sustainability. The DAF guides a holistic context-aware process formulation for a given DI. An evidence-based evaluation within the DAF protocol benchmarks a specific DI’s impact against the SDG indicators framework. The participating experts worked together to identify a DI and gather and analyze evidence by operationalizing the DAF. The four DIs identified in the process are as follows: smart home technology (SHT) for energy efficiency, the blockchain for food security, artificial intelligence (AI) for land use and cover change (LUCC), and Big Data for international law. Each of the four expert groups addresses different DIs for digitainability assessment using different techniques to gather and analyze data related to the criteria and indicators. The knowledge presented here could increase understanding of the challenges and opportunities related to digitainability and provide a structure for developing and implementing robust digitainability practices with data-driven insights.