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 important 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 it creates will help us align it with 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. We performed the impact assessment of diverse technologies using DAF. This paper summarizes the insights from the Digitainable Spring School 2022 on "Sustainability with Digitalization and Artificial Intelligence," one of whose goals was to operationalize the DAF as a tool in the action learning process with 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 operationalization of the DAF was carried out by looking at four different DIs: smart home technologies (SHT) for energy efficiency, blockchain for food security, artificial intelligence for land use cover and changes (LUCC), and big data for international law. Each of the four studies addresses different DIs for digitainability assessment using different techniques for a diverse group of indicators, demonstrating the potential of the DAF but also outlining the existing data gaps that limit a comprehensive analysis.