Remote workforces using VPNs, cloud-based infrastructure and critical systems, and a proliferation in phishing attacks and fraudulent websites are all raising the level of risk for every company. It all comes down to just one thing that is at stake: how to gauge a company's level of cyber risk and the tolerance level for this risk. Loosely put, this translates to how much uncertainty an organization can tolerate before it starts to negatively affect mission critical flows and business processes. Trying to gauge this can be a huge and nebulous task for any IT security team to accomplish. Making this task so difficult are the many frameworks and models that can be utilized. It is very confusing to know which one to utilize in order to achieve a high level of security. Complicating this situation further is that both quantitative and qualitative variables must be considered and deployed into a cyber risk model. Assessing and Insuring Cybersecurity Risk provides an insight into how to gauge an organization's particular level of cyber risk, and what would be deemed appropriate for the organization's risk tolerance. In addition to computing the level of cyber risk, an IT security team has to determine the appropriate controls that are needed to mitigate cyber risk. Also to be considered are the standards and best practices that the IT security team has to implement for complying with such regulations and mandates as CCPA, GDPR, and the HIPAA. To help a security team to comprehensively assess an organization's cyber risk level and how to insure against it, the book covers: The mechanics of cyber risk Risk controls that need to be put into place The issues and benefits of cybersecurity risk insurance policies GDPR, CCPA, and the the CMMC Gauging how much cyber risk and uncertainty an organization can tolerate is a complex and complicated task, and this book helps to make it more understandable and manageable.