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The literature on trust seems to have reached a consensus that appropriately calibrated trust in humans or machines is highly desirable; miscalibrated (i.e., over- or under-) trust has been thought to only have negative consequences (i.e., over-reliance or under-utilization). While not invalidating the general idea of trust calibration, a published computational cognitive model of trust in strategic interaction predicts that some local and temporary violations of the trust calibration principle are critical for sustained success in strategic situations characterized by interdependence and uncertainty (e.g., trust game, prisoner’s dilemma, and Hawk-dove). This paper presents empirical and computational modeling work aimed at testing the predictions of under- and over-trust in an extension of the trust game, the multi-arm trust game, that captures some important characteristics of real-world interpersonal and human-machine interactions, such as the ability to choose when and with whom to interact among multiple agents. As predicted by our previous model, we found that, under conditions of increased trust necessity, participants actively reconstructed their trust-investment portfolios by discounting their trust in their previously trusted counterparts and attempting to develop trust with the counterparts that they previously distrusted. We argue that studying these exceptions of the principle of trust calibration might be critical for understanding long-term trust calibration in dynamic environments.