Critical success factors such as trust and privacy concerns have been recognized as grand challenges for research of intelligent interactive technologies. Not only their ethical, legal, and social implications, but also their role in the intention to use these technologies within high risk and uncertainty contexts must be investigated. Nonetheless, there is a lack of empirical evidence about the factors influencing user's intention to use insurance chatbots (ICB). To close this gap, we analyze (i) the effect of trust and privacy concerns on the intention to use ICB and (ii) the importance of these factors in comparison with the widely studied technology acceptance variables of perceived usefulness and perceived ease of use. Based on the results of our online survey with 215 respondents and partial least squares structural equation modelling (PLS-SEM), our findings indicate that although trust is important, other factors, such as the perceived usefulness, are most critical for ICB usage.