Our analysis in this Executive Update builds upon the challenges and risks we outlined in a previous Update, which showed how managers in regulated firms face a quandary: whether to play it safe and lock out cloud-based innovations and correspondingly lock themselves out of related innovations or to negotiate a rocky course, balancing the risks associated with these technologies and regulatory expectations. This Update provides a detailed assessment to help management understand when to strategically engage with cloud technologies and when to avoid them, thereby helping executives balance the need to innovate with the need to manage compliance risk. Our assessment, based on research and data collection conducted from 2014-2016, allows managers to evaluate the criticality of impacted services to maintaining compliance along with managers’ ability to understand and control transparency and supervision over cloud arrangements.