This paper will identify the relation between transgression in spiritual practices for self-divinization and its relation to magical practices. Within the context of contemporary magic, emphasis is placed by specific groups or individuals on the intentional violation of perceived taboos concerning society and conventional spiritual practices. Examples of these regard the international Swedish based order of the Dragon Rouge, which concentrates on the pursuit of a “dark spirituality” associated to the Left- Hand path in opposition to mainstream “light spirituality” defined as Right-Hand path. Secondly, Thelema traditionally incorporated practices such as sex magic, drug use and violation of religious norms within specific historical contexts for the purpose of ceremonial practices and personal liberation. Thirdly, the practice of Chaos Magic and related pop cultural environment which aspires to the subversion of order whether social spiritual or cultural. Finally, groups which, although controversial in the research field are, however, culturally relevant and incorporate criminal activity as part of self-development in contrast to a perceived weak society such as in the case Order of Nine Angles. Although these four cases incorporate transgression in their ideals and practices on different levels they nevertheless are oriented towards personal transformation either identified with becoming independent, acquiring divine status or of transmutation into an ideal version of oneself. The latter is more commonly translated into terms of freeing oneself from the shackles of an oppressive normality and taking control of one’s reality. I will thus analyze the similarities and differences in the intention behind the various magical or spiritual practices performed by these groups to understand whether, through varying levels and expressions of transgression, there is a common thread that unites transgression, magical practice and spiritual development.