Transformative theories of human nature posit that the genus of animality is wholly transformed by the specific difference of reason. The aim of this paper is to show that the two most prominent transformative approaches, ‘resolute’ and dialectical’, face a dialectical impasse that Helmuth Plessner’s philosophical anthropology is able to resolve. First, I outline objections to the resolute approach which motivate the ‘dialectical’ turn to second nature. Second, I show that the dialectical approach faces a dilemma. It either runs into an internal ‘interaction problem’ by its qualitative distinction of nature and spirit. Or it assimilates both in a way that either amounts to a collapse into the resolute approach or which creates the problem of a merely ‘artificial naturalness’. Third, I reconstruct Plessner’s ‘form-typological’ approach to how the genus living being is differentiated into structural types. This enables a dilemma-free rendition of transformation as ‘natural artificiality’: it is human first nature to seek embodied expression in second nature.