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Studies on stress and decision-making usually address acute and artificial stressors. However, COVID-19 outbreak set the perfect scenario to address how decision-making, and specifically loss aversion, could be affected by a real and persistent stressor, able to promote a significant psychological distress. In parallel, alexithymia has been identified as a potential moderator of the loss aversion expression, since it could impair the incorporation of emotional information when making a decision, leading to “cold” decisions. Through a within-subjects design (N = 70), our aim was to study the relationship between the psychological distress caused by the pandemic context and the loss aversion changes, considering alexithymia as a moderating factor. Our results show a significant increment in both psychological distress and loss aversion, merely one month after the confinement’s onset. Moreover, both variables were positively associated only when alexithymia was low, i.e., the alexithymia buffered the effect of psychological distress on decision-making: a higher alexithymia implied a lower loss aversion increase.