Assessing security risks of users in a computing network

A security system, comprising:

• at least one processor;
• and
• memory storing instructions that, when executed by the at least one processor, cause the security system to:
• generate an interaction item, wherein the interaction item comprises one or more of a training item or a security item;
• transmit the interaction item to an end user electronic device via a network;
• receive feedback data from the end user electronic device,
• wherein the feedback data comprises sensed data relating to an action of a user of the end user electronic device associated with the interaction item, and
• wherein the feedback data comprises technical information associated with the end user electronic device;
• compare the feedback data to a plurality of security risk scoring metrics;
• based on comparing the feedback data to the plurality of security risk scoring metrics, determine a security risk score, wherein the security risk score quantifies a cybersecurity risk presented by the user of the end user electronic device;
• generate a subsequent interaction item based on the security risk score, wherein the subsequent interaction item comprises one or more of a training item or a security item, and wherein the subsequent interaction item includes a number of fields, each field of the number of fields having an associated value;
• assign a weight to each field of the number of fields based on the field's associated value;
• and
• determine a sophistication score for the subsequent interaction item by totaling the weights associated with each field of the number of fields.

One or more non-transitory computer-readable media storing instructions that, when executed by a security system comprising at least one processor and memory, cause the security system to:

• generate an interaction item, wherein the interaction item comprises one or more of a training item or a security item;
• transmit the interaction item to an end user electronic device via a network;
• receive feedback data from the end user electronic device,
• wherein the feedback data comprises sensed data relating to an action of a user of the end user electronic device associated with the interaction item, and
• wherein the feedback data comprises technical information associated with the end user electronic device;
• compare the feedback data to a plurality of security risk scoring metrics;
• based on comparing the feedback data to the plurality of security risk scoring metrics, determine a security risk score, wherein the security risk score quantifies a cybersecurity risk presented by the user of the end user electronic device;
• generate a subsequent interaction item based on the security risk score, wherein the subsequent interaction item comprises one or more of a training item or a security item, and wherein the subsequent interaction item includes a number of fields, each field of the number of fields having an associated value;
• assign a weight to each field of the number of fields based on the field's associated value;
• and
• determine a sophistication score for the subsequent interaction item by totaling the weights associated with each field of the number of fields.