Abstract: Aspects of the disclosure relate to dynamic cybersecurity event detection and training functions. A computing platform may monitor a plurality of user devices to detect a cybersecurity training triggering event. In response to the detection, one or more cybersecurity training session prompts may be generated and transmitted to one or more user devices. User input providing a response to the cybersecurity training session prompt may be evaluated for accuracy and scored for the cybersecurity training session. In some examples, an overall cybersecurity score for a user may be maintained and modified based on the score for the cybersecurity training session. One or more modifications may be identified and executed based on the scores generated.