Digital transformation often changes more than technologies. It can unsettle routines, expertise, relationships, status arrangements, and understandings of what an organization has been and should remain. Such disruptions create conditions in which employees may look backward, yet backward orientation is frequently treated either as resistance or as benign attachment to organizational history. This Original Conceptual Theory Article develops a more conditional account. It proposes the Theory of Transformation Nostalgia, explaining how perceived discontinuity between valued organizational identity and emerging digital arrangements may activate organizational nostalgia and how selective memorialization may subsequently channel that nostalgia toward different responses. Three proposed pathways are distinguished: temporal-bridging nostalgia, in which valued elements of the past are connected to a credible future identity; defensive-restorative nostalgia, in which an idealized past becomes a benchmark for preserving or restoring prior arrangements; and rhetorically mobilized nostalgia, in which organizational actors selectively invoke history to legitimate competing transformation claims. Threat attribution, identification, burnout, job insecurity, perceived technological replacement, future-continuity credibility, institutional legitimacy, and narrative power are proposed as boundary conditions. The theory does not presume that nostalgia obstructs change or improves it. Its contribution is an explicitly non-validated framework linking nostalgia, identity protection, memory selection, resistance, and sensemaking while preserving boundaries between individual and organizational inference, memory and history, association and causation, and conceptual plausibility and empirical validation.