There are numerous risks associated with the interconnection of healthcare provision and the Internet of Things (IoT), with its sensory capabilities shown to reduce confidence in novel technology due to fears of a loss of privacy. There exists a clear omission in the extant literature—consideration of gender differences in Frontline Healthcare Providers’ (FHP) behavioural intentions—which this work aims to address through the analysis of IoT-enabled healthcare applications’ (HAs) behavioural intentions in multicultural and bi-generational (Gen X, Y) context. Essentially, analysing gender and generational differences in relation to the variables (privacy, security and trust that influence risk perception; the latter alongside attitude and perceived behavioural control potentially affect the intention) affecting FHPs’ BI towards IoT enabled HAs. A novel model is presented herein, which combines Planned Behaviour (TPB), Privacy Calculus (PCT), and the trust-risk framework. Questionnaire methodology (n = 401) was applied to both generations under consideration, data was assessed using Partial Least Squares Multi-Group Analysis (PLS-MGA), which showed gender differences in Gen Y, but there was little evidence to suggest that risk perception affects any of the cohort's behavioural intention towards the use of IoT-enabled HA, which in turn should help guide both future institutional policy and application development.