Systems, apparatus, and methods of authentication utilizing contextual data to authenticate individuals and prevent security breaches are described herein. An example proxy engine may monitor interactions with a computing device to obtain contextual data unique to a user. The contextual data may be utilized to generate unique challenge questions in response to requests for access to a secure resource, and may eliminate the need for a user to remember credentials to access the resource. Challenge questions may be limited to a single use and vary in difficulty in proportion to the value of the resource. In response to correct responses to challenge question(s), the proxy engine may access a vault containing a credential authorizing access to the resource. The vault and proxy engine may be entirely contained on the computing device or they may be implemented on a remote apparatus accessed via an application or interface on the computing device.