The ultramodern condition represents the "third wave" in postmodernist-inspired philosophy and cultural practice. Two of ultramodernism's critical theoretical components are the human/social forces, flows, and assemblages that sustain transgression; and the human/social intensities, fluctuations, and thresholds that make transcendence possible as both will and way. In the ultramodern age, then, transcendence is about overcoming and transforming the conditions (i.e., forces, flows, and assemblages) that co-produce harm-generating (i.e., transgressive) tendencies. This manuscript problematizes transgression by way of ultramodern theory. This critical investigation represents "the phenomenology of the shadow," or the ultramodern philosophy of harm. To contextualize this phenomenology and philosophy, the intellectual history of ultramodern thought is recounted. This includes a review of the shadow construct by way of its prominent socio-cultural, psychoanalytic, and political-economic currents; and a chronicling of the reification process (regarding risk, captivity, and harm) since the modernist era (i.e., the industrial revolution). The article concludes with some very speculative observations concerning "the phenomenology of the stranger," or the ultramodern philosophy of transcendence as both will and way.