During the last decade and as a result of the 2008 global financial crisis, Enterprise Risk Management (ERM) gained more attention from the financial services sector especially banks and insurance companies. In addition, many companies had adopted practices dedicated to ERM and consulting firms started to establish departments specialized in ERM. Meanwhile, universities have developed specializations related to ERM. Moreover, research centers embarked on research on this subject matter. This study aims to investigate the reality of enterprise risk management in the Jordanian insurance industry in order to reveal the challenges facing it by focusing on the four most important dimensions related to enterprise risk management which are: governance and risk management strategy, risk culture, risk management operations and its interdependencies, and finally the support technology for risk management. The study is based on the descriptive inductive methodology in building the questionnaire, which was distributed to a sample that consisted of most insurance companies in Jordan during the period from December 2015 to February 2016. The study found that risk management practices and regulatory authorities have a long way to go, where the most important results of this study were: 28% of the insurance companies surveyed have a plan and a budget for Information Technology (IT) risk management. The support level of technology to the risk management in the insurance companies surveyed is 30%. 33% of the insurance companies surveyed have standard practices in the enterprise risk management, such as: ISO 31000 and COSO standard. 33% of the insurance companies surveyed currently have a risk management system. 37% of the insurance companies surveyed were a target of electronic attacks over the past 18 months. 47% of the insurance companies surveyed have a risk management department that is responsible for adhering to regulatory and legislative requirements set by the legislator. 49% of the insurance companies surveyed, are evolving universities, consulting firms and specialized training centers, in developing and enhancing risk management personnel. 56% of the insurance companies surveyed are willing to have a risk management program 60% of the insurance companies surveyed have an accredited policy of risk management The level of the risk management operations and its interdependence in the insurance companies is 64% The level of the governance of risk management and its strategy in the insurance companies is 69% Based on these results and in order to begin to improve the reality of risk management practices in the Jordanian insurance companies, the researcher has the following recommendations: Activating the role of risk management through the establishment of specialized departments in this field. Activating the role of the legislative and regulatory authorities to play a bigger role in order to confirm the existence of these departments and to improve procedures and instructions provided by these actors in this area. Increasing the role of academia represented by universities, consulting firms and specialized training centers, to ensure improving the efficiency of the staff of risk departments. Encouraging the companies through the regulatory authorities to adopt global standards in risk management, such as: ISO 31000 COSO standards. Encouraging the companies to have a plan and a budget for the information technology risk management. Directing companies to have accredited policies in risk management. Drawing the attention of the companies to the importance of technology information in the risk management systems and the confidentiality of their information. Drawing the attention of companies to raise the level of management in the governance and risk management strategies in the insurance companies. Inducing to increase the level of risk management operations and its interdependencies among insurance companies. Drawing the attention of researchers and academia to the importance of research and scientific studies in this area to demonstrate its importance to the Jordanian insurance companies, to increase the desire and willing of the insurance companies to adopt risk management programs, at present time and in the future.