Techniques for enhancing actionable opportunities through machine learning are disclosed. In some embodiments, a system includes an event listener for detecting an opportunity to perform an action using one or more computing resources. When a new opportunity is detected, the system generates a set of search criteria, which is used to search a set of external web resources for current events. The system may then generate, using a machine learning model as a function of one or more features extracted from current events satisfying the search criteria, a score representing a likelihood of success that the action leads to an optimal result. The system may tune the machine learning model based on feedback received that is indicative of how the current events affected the likelihood of success for the action.