Can a catalog “care” about its users? This question, introduced at the first Ethics of Information Organization conference in 2009, asked whether catalogs adhere to the ethic of care, the theory put forward by Tronto (1994) and others that calls for context and flexibility in ethical decision-making. This keynote address for the 4th International Conference on the Ethics of Information & Knowledge Organization expands on that question, adapting the notion of the “uncanny valley” (Mori 1970), where the ability for a catalog to “care” is disrupted by ethical decisions that cause conceptual violence for its users. This keynote address provides an informal summary of the first three Ethics in Information Organization conferences, identifying themes that have been acted upon in practice, ethical challenges knowledge organization continue to face, and new challenges that have emerged, demonstrating that a “caring” catalog is still a work in progress.