A system and method are provided for prompting blood pressure-related calibrations. The method relies on statistical hypothesis tests over a current measurement and an accumulated set of calibration points to determine whether the benefit of calibration, in terms of calibration diversity, outweighs the cost to the patient. The algorithm uses statistical methods to predict calibration effect without actually performing the calibration, hence, reducing the calibration ‘cost’ to the patient and increasing the diversity of calibration points and thereby improving PWV-BP transform quality. The method is applicable to both manual and automatic calibration modes.