Reflecting the IFIP 8.6 theme of “cocreating for context,” this conceptual contribution proposes a model designed to support co-creation within an unfolding context of varying internal and external conditions as a digital transformation (DT) strives to achieve its goals. It proposes a digital transformation progress model (DTPM) that combines a work system perspective with ideas related to DT, including DT initiative, DT success, phases of DT, and tangible and intangible resources for change that affect DT initiatives. The model expresses the combined impact of the favorability of five categories of resources for change at any point in a DT initiative’s trajectory. The categories are momentum, capabilities, forces, drivers and impediments of change, and catalysts of change. Potential uses of the DTPM and follow-on research are discussed briefly.