Digital transformation can positively or negatively contribute to societies, organizations, and individuals depending on the values inscribed in the underlying digital technologies. This highlights the importance for researchers to critically examine digital technologies’ value inscriptions, how technology use enacts these values and the bearing of these values on research. This paper draws on the pre-ICIS 2022 IFIP 8.2 OASIS workshop on “Criticality and Values in Digital Transformation Research" to highlight four ways researchers can practice criticality, that is, how they can identify and reflect on the values that underlie digital phenomena. The types of criticality are phenomenon-based, method-based, theory-based, and self-reflexive criticality. Criticality alone does not constitute critical social research. However, criticality sensitizes researchers to consciously engage with values, which can feed into critical research’s elements of insight, critique, and transformation. Criticality can inform insight by surfacing values; providing the basis for critique by confronting readers with alternative values; and supporting transformation by proposing alternative value inscriptions. Hence, we take criticality as pivotal for understanding how digital transformation can contribute to building a better world and we invite the IS community to practice and discuss criticality, values, and reflexivity to drive positive change.