When grief over the death of a loved one becomes complicated, protracted and circular, ruminative counterfactual thinking in which the bereaved relentlessly but vainly seeks to somehow reverse the tragedy of the loss often plays a contributory role in sustaining the person's suffering. In this article we summarize the growing evidence implicating this cognitive process in interfering with meaning reconstruction following loss, and identify four foci for counterfactual, "if only" cognition, directed at the self, the deceased, relevant others, or the circumstances of the death itself. We then illustrate each with an actual case vignette, along with approaches to resolving, dissolving, mitigating, or redirecting such rumination, and conclude with a general principle of practice for other therapists whose clients struggle with similarly anguished and entrenched counterfactual preoccupations.