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Energy security has become very important in the current energy regime of the world. This paper proposes an assessment framework for measuring energy security named Holistic Energy Security Index (HESI) and then reports a study that used it to measure the energy security of Thailand for the time period of 2007-2030. The HESI is formulated to assess energy security under six main themes which are base diversity, oil security, gas security, vulnerability, sustainability and energy development, and each of these themes has sub-indicators which indicate the level of security in each theme. The Thai energy system has been modeled using an integer programming based optimization model called "Model for Energy Supply Strategy Alternatives and their General Environmental Impacts" (MESSAGE). The energy system has been modeled as an individual case study consisting of 10 scenarios, which include different policy options and measures in the power sector such as Integrated Resource Planning (IRP), Low Carbon Society (LCS) and nuclear power technology. Results indicate that in comparison to the year 2007, the energy security of Thailand has a decreasing trend in the reference scenario. In terms of enhancing energy security, the IRP scenario performs the best followed by LCS and Combined (COM) scenarios. The oil security of Thailand is not increased significantly by the policy options modeled. The gas security is increased by nuclear technology, and by IRP measures. There is significant occurrence of mitigation of local air pollutants such as SO2 and NOx along with CO2 mitigation. [ABSTRACT FROM AUTHOR]