A computer-implemented system, method and medium for assessing the risk of and/or determining the suitability of a system to comply with at least one predefined standard, regulation and/or requirement. In at least some embodiments of the present invention, the method comprises the steps of: 1) automatically or manually gathering information pertaining to the system, 2) selecting one or more requirements with which the system is to comply; 3) testing the system against the requirements; 4) performing risk assessment of the failed test procedures, and 5) generating certification documentation based on an assessment of the first four elements.