Background: Nursing students and nurse preceptors indicate that a comprehensive orientation is vital to successful work-integrated learning placements in Prison Health Services. The aim of this study was to implement and evaluate a Prison Health Service orientation package that included innovative asynchronous online video simulations with branched decision-making and feedback opportunities to stimulate learning and improve students’ feelings of preparedness for a placement in this setting. Methods: A cross-sectional pre and post design was used to evaluate the resource. Students were given access to the package and invited to complete a pre-placement survey evaluating the resource and their feelings of preparedness for placement. Following placement, they re-evaluated the resource in terms of how well it prepared them for the placement and how well prepared they felt. Third year Australian undergraduate nursing students from one university who completed a Prison Health Service work-integrated learning placement in 2018, 2021, and 2022 were invited to participate. Placements were unavailable in 2019 and 2020. Independent t-tests were used to determine differences in scale means and level of preparedness between pre- and post-survey responses. Results: Twenty-three of 40 (57.5%) eligible nursing students completed the pre-placement survey and 13 (32.5%) completed the post placement survey. All respondents to the pre-placement survey indicated that they felt satisfactorily, well, or very well prepared after completing the orientation package prior to their clinical placement. Students were significantly more likely to consider themselves well prepared by the package after they had attended placement (p < .001). All students post placement indicated that overall, the simulation resources and the specific simulation scenario about personal boundaries and management of manipulative behaviours was useful for their placement. The majority of students would recommend the orientation package to other students. Suggestions for improvement included streamlining the resource to reduce the time to complete it. Conclusions: Asynchronous online simulation with the capacity for branched decision making and feedback along with a comprehensive online orientation package were perceived as useful to prepare undergraduate students for placement in the Prison Health Service work-integrated learning setting.