A system for implementing discriminated cybersecurity interventions in a population of users includes a prompt module presenting a plurality of prompts including a first prompt set corresponding to a risk assessment and a second prompt set corresponding to a rule assessment, a response module receiving a first response set corresponding to the first prompt set and a second response set corresponding to the second prompt set from a user of the population of users, an evaluation module determining a first score of the user corresponding to the first response set and the risk assessment and determining a second score of the user corresponding to the second response set and the rule assessment, and an intervention module implementing a discriminated cybersecurity intervention for the user based on the first score and the second score.