How does failure emerge and develop during organizational change? As organizations are pushed for change, the notion of failure that relates to change becomes gradually ingrained in contemporary research. However, with studies having primarily added to the conversation from a static outset, extant scholarly work might not fully capture the transience that marks change in essence. This article contributes to the literature on failure in change by advancing a dialectical perspective, offering the scholarly community insight in the emergence and development of failure as happening in three processes. In a retentive process, change agents adhere to a change approach deemed successful in spite of alternatives emerging, causing tensions to gradually build within the organization’s social atmosphere. In a reactive process, looming tensions find themselves affirmed and flare up, instigating the display of a new change approach that is antithetical to the one initially adhered to. Finally, in a recursive process, organizational members collectively recall the positive aspects of prior failure, smoothening organizational change towards re-combinatory synthesis. Marking failure’s emergence and development as a dialectic, this article notes failure in organizational change to be as generative as it is deteriorating, paving the way for both success and failure to continuously remit.