Collection and monitoring of specific indicators may enable dynamic and proactive risk assessment. In fact, such collection, improved by today's advanced information technology systems, may provide real-time information on the overall risk variation. Moreover, monitoring human and organizational factors may allow prevention of potential underlying causes of accidents. Four classes of proactive approaches for dynamic risk assessment are presented in this chapter. They represent four levels of connection to the overall risk picture, from connection assumed on the basis of past accident analysis to dynamic aggregation methodologies. The risk barometer technique is presented as representative example of the latter. Its attention to human and organizational factors is demonstrated not only by real-time collection of specific indicators but also by its capability to support key safety decision-makers in short- and medium-term planning.