Background: Radicalization, violent extremism, and terrorism are risks to societal security. Although research on terrorism-related behaviors is increasing, thorough empirical studies are rare. Methods: This study investigates radicalization processes and transitions in a matched sample of female and male terrorist suspects and convicts (N = 26) residing in Dutch penitentiary terrorism wings. Results: Results show that both men and women often experienced discrimination. A subgroup of women grew up in a stressful family environment and lacked emotional support from their family, whereas the other women did not experience such circumstances. The majority of the study sample was susceptible to connecting with radicalized friends or family members. Interestingly, factors that initially led to radicalization (e.g., a utopian image of the Islamic State) could later turn out to be factors associated with abandoning extremism. Conclusions: In this study, differences in radicalization processes and transitional phases between women and men emerged. Men more often had police contact prior to a terrorism-related offense. Making an effort to right old mistakes seemed important in the radicalization processes of men, whereas women had a stronger desire for emotional support and were more driven by experienced trauma and feelings of loneliness. This study provides input for gender-specific prevention and disengagement interventions.