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We demonstrate two interpretations of observational entropy, one as the statistical deficiency resulting from a measurement, the other as the difficulty of inferring the input state from the measurement statistics by quantum Bayesian retrodiction. These interpretations show that the observational entropy implicitly includes a uniform reference prior. Since the uniform prior cannot be used when the system is infinite-dimensional or otherwise energy-constrained, we propose generalizations by replacing the uniform prior with arbitrary quantum states that may not even commute with the state of the system. 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