One way that Hypothesis can open the platform to user-generated content is through features that enable monetizable Context, where users can earn revenue from the content they create for and publish on the platform. This could function like newsletter publishing platforms, where creators can acquire paying subscribers who depend on their insight, or it could be implemented as part of a revenue-sharing policy that fits saliently within Hypothesis’ existing incentive structures, where the authors of a question's most useful Context would be given a portion of the platform’s subscription revenue generated by the wider Hypothesis community. We plan to further investigate the implications of these potential features on the larger Hypothesis community relationship with Context that originates from outside the platform. We believe it is crucial to understand some critical questions, like: will users become less likely to share or interact with Context when there is a saturation of on-platform content competing for placement on predictions? And is there a meaningful difference between on-platform user-generated Context and off-platform publisher-generated Context when it comes to Foresight and Usefulness?