Aspects of the disclosure relate to providing training and information based on simulated cybersecurity attack difficulty. A computing platform may retrieve data associated with a plurality of attack templates for simulating cybersecurity attacks. Subsequently, the computing platform may use one or more models to compute a predicted failure rate for each template of the plurality of attack templates in order to yield a plurality of predicted failure rates for an organization. Based on the plurality of predicted failure rates, the computing platform may use one or more of the plurality of attack templates to configure a simulated cybersecurity attack on the organization. Then, the computing platform may send, via the communication interface, to an administrator user device associated with the organization, information about the simulated cybersecurity attack and may execute the simulated cybersecurity attack.