Cornelius Agrippa, a famous German humanist, philosopher, and occultist, attempted to create a synthesis of various spiritual traditions with the intention of reforming Christianity struck by a major crisis. His program of “enriching” Christianity by embracing various doctrines of Neoplatonism, Cabala, and Hermeticism ultimately failed, and yet it opened a range of questions concerning the problem of interaction between different religions and their paradigms. This work offers a detailed examination of one particular paradigm strongly present in Agrippa’s thought, that of spiritual ascension. It analyzes the ways he shaped his understanding of ascension and argues that these inevitably led to the emergence of two conflicting notions: that of mystical ascension (the mystic’s attempt to free himself of the bonds of corporeality) and magical ascension (the magus’ attempt to become like God and control the forces of nature), positioning Agrippa somewhere halfway between a magical and a mystical thinker. This study will be a useful tool to the students of western esoteric traditions and early modern intellectual history in general.