As AI systems move from static repositories to agents that are capable of continual adaptation and learning, maintaining their trustworthiness means equipping the models backing them with the ability to produce confidence estimates that dynamically reflect their changing skills and knowledge. We introduce the problem of persistent calibration, which requires a confidence estimator to faithfully reflect the knowledge contained in a model as that knowledge changes, without recurring supervision. We operationalize this by examining persistent calibration across checkpoints of open models, asking whether confidence estimators trained on earlier checkpoints can generalize to later ones. Specifically, we aim to shed light on whether confidence is dependent on knowledge, a question with implications for the reliability of confidence estimates. To measure this relationship, we define and evaluate calibration on knowledge contrast sets: subsets containing questions that one checkpoint answers correctly and another checkpoint answers incorrectly, reflecting a change in knowledge. We show that both inference-time and fine-tuning methods fall short on contrast-set calibration compared to oracle methods trained on future checkpoints, even for methods that are well-calibrated on the full dataset. We provide evidence for the hypothesis that persistent calibration is challenging because there is a vast space of possible confidence functions that are well-calibrated on a given checkpoint, out of which only some rely on meta-knowledge features that would generalize to other checkpoints. Towards improving contrast-set calibration, we show that multi-checkpoint training helps, suggesting an avenue for identifying confidence features that remain robust across changing knowledge.

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