While the public claim to be concerned about privacy, they rarely express protective behaviour. This disparity has been labelled the Privacy Paradox. The Internet-of-Things (IoT) is ubiquitous and data-collecting. It has therefore been considered a privacy risk. However, the Paradox has not been assessed in this context. Hence, we explored whether the issue could be mitigated in novel environments. Before analysing these devices, we began by confirming the Paradox's prevalence. This was undertaken through street surveys, which suggested that views had little relationship with behaviour. We continued by comparing user perceptions across a range of technologies. Through an online survey [n = 170], participants rated 'IoT' devices as most concerning. They were also considered less usable, potentially placing constraints on protection. To dissect the issue, we then conducted detailed interviews. Discussions were undertaken with 40 users, 20 of which had an IoT product. Protection was less common in the IoT, contributing to greater Paradox prevalence. Wearables were particularly prone, and therefore we scoped our focus to smartwatches. Through analysing participant rationale, a lack of awareness appeared the greatest IoT issue. Since educational games had proved effective in the literature, we developed privacy apps. Our online prototype was trialled by 504 smartwatch owners. In our treatment group, we found the Paradox was mitigated in posttest results. Therefore, for our final study, we implemented the first smartwatch privacy game. Through a two-month longitudinal study, we analysed empirical behaviour. Users were given an (Android) Wear OS watch, with half playing the game. Protection increased and persisted in this group, with the Paradox mitigated over an extended period. Our research has novelty, in that this has not been achieved in previous work. Furthermore, by analysing smartwatch behaviour, we provide novel insights into user rationale. As the IoT expands, it is crucial that individuals are informed to make privacy decisions.