Chest radiography (CXR) diagnosis is critical for thoracic disease assessment, yet challenged by the need to identify subtle lesions and co-occurring abnormalities across regions. While recent vision-language models can actively observe local regions, existing preference-based methods supervise each observation by its immediate effect on the current diagnosis, failing to capture how each observation and stopping decision contributes to the final diagnosis. To address this issue, we propose GroundSeek-CXR, an active CXR diagnosis framework that learns observation and stopping decisions by retrospectively evaluating them with the final diagnosis. Specifically, we first devise a Retrospective Diagnostic Evaluation (RDE) that scores observation and stop candidates from offline Monte Carlo tree search through independent continuations. Moreover, we design a Retrospective Gap-weighted Preference Optimization (RGPO) that learns from retrospective-score preferences weighted by their score gaps, prioritizing actions that improve diagnostic accuracy. Extensive experiments demonstrate that our GroundSeek-CXR framework outperforms state-of-the-art methods, and improves abnormal-image sample-F1 by 4.48% over immediate-score preference learning.

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