Abstract: The present invention provides systems and methods utilizing tokens to assign or mitigate risk. A software token is provided that associates a secret—such as a private key or password—with risk factors involved in protecting that secret from illicit access. The token may include an indication or calculation of the “overall risk of compromise” (OROC), generally represented as an overall trust metric, associated with the secret. This token can then be used to inform system operators or third parties of the confidence of a given system transaction that depends on the secret. A third party can then take whatever actions it deems appropriate according to the estimated risk. For example, in one embodiment of the present invention, the risk factor is used to deny a transaction if the risk is deemed to great—that is if the risk factor is greater than a predetermined (or sufficient) value.