The scholarship on radicalization to violence often treats born Muslims and converts interchangeably; far too little research is focused on understanding the factors and processes driving converts in particular. This is a problem given that there is overwhelming evidence demonstrating that Muslim converts are overrepresented among Western foreign fighters. Data from Canada corroborates this larger point: converts are highly representative in attempted and successful domestic terrorist attacks. Our article explores conversion to Islam and political violence as it relates to recent trends in Canadian Jihadist militancy. We distill the theoretical literature on conversion and radicalization to seven explanatory factors, including ideology; social networks; charismatic authority; political grievances; psychology; socio-economic and criminal circumstance; and enabling environments. We then build original empirical case studies – based on expert interviews and open-sourced documents – of three Canadian converts who engaged in terrorism, including John Maguire, Michael Zehaf-Bibeau, and Damian Clairmont. Using these case studies, we contextualize, analyze, and expand our collective understanding of conversion to violence, providing lessons for theory and methodology.