Security challenge assisted password proxy

A method for contextual authentication, comprising electronic operations performed with processor circuitry of a computing system, the electronic operations comprising:

• obtaining user interaction data from a plurality of user activities performed with a user interface of a computing device;
• obtaining contextual data that includes at least two of:
• activity data collected from an activity sensor of the computing device, event data collected from a calendar data source of the computing device, and location data collected from a location sensor of the computing device;
• determining a security level of a credential stored in a set of encrypted user credentials;
• generating, responsive to a request for access to the credential in the set of user credentials, a textual challenge question and a textual challenge answer based on the user interaction data, the contextual data, and the security level;
• display, in the user interface of the computing device, the textual challenge question;
• receive a response to the textual challenge question from a user, via the user interface;
• evaluating the response to the textual challenge question against the textual challenge answer to determine whether the response to the textual challenge question is correct;
• and
• transmitting the credential to a secure resource over a network responsive to determining that the response to the textual challenge question is correct.

A computing device, comprising:

• a sensor adapted to obtain contextual data based on user activity with the computing device, wherein the contextual data includes activity data collected from the sensor and event data collected from a calendar data source of the computing device;
• a data store adapted to store the contextual data;
• a memory adapted to provide a secure password vault to store a set of encrypted user credentials;
• and
• processor circuitry adapted to execute a plurality of instructions to implement:
• a user interface adapted to receive a request for a secure resource;
• a proxy interface adapted to intercept the request for the secure resource received by the user interface;
• and
• a proxy engine adapted to monitor the calendar data source and the sensor, the proxy engine adapted to store the contextual data in the data store wherein, responsive to the request for the secure resource intercepted by the proxy interface, the proxy engine is adapted to:
• determine a security value of the secure resource;
• generate a textual challenge question and a textual challenge answer based on the contextual data in the data store, the textual challenge question being presented via the proxy interface;
• generate an additional textual challenge question and an additional textual challenge answer, responsive to the security value being greater than a set security level, the additional textual challenge question and additional textual answer based on the contextual data in the data store;
• prevent access to the secure resource until a correct answer to the textual challenge question and the additional textual challenge question is received;
• and
• transmit a credential that corresponds to the secure resource, from the set of encrypted user credentials, to the secure resource.