Radical conversion, which entails a sweeping transformation of existing meaning systems, is often precipitated by emotional distress. Nevertheless, although many individuals turn toward religion when distressed, few undertake total and radical conversions. Previous research suggests that insecurely attached individuals—who resemble James's disillusioned, doubting, and divided sick souls—may be particularly prone to radical conversions. Thus, the present research examined insecure parental attachment history and convert status among 122 Orthodox and 31 non-Orthodox Jews, hypothesizing that converts to and from Orthodox Judaism, who undertake an all-encompassing transformation of beliefs, behaviors, values, and life's purpose, would report greater insecurity in parental attachment history than nonconverts. Results indicate that converts report greater maternal and paternal insecurity, as compared to both nonconverts and those with intra-Orthodox religious change. Thus, further research examining insecure attachment, and associated religious stressors and doubts, may uncover some of the individual differences underlying radical conversions.