Thailand’s unique and special context is described in ways which augurs well for Thailand’s educational future. Four major paradoxes are then identified, the major one being that despite Thailand spending a large percentage of its national budget on education, outcomes and results have been disappointing. Key trends (both successful and problematic) are then identified. Key positive ones are the rapid quantitative expansion of education, the massification of higher education, and Thai students being among the most happy in the world and some being among the most talented. Key problematic trends are synthesized in a tetrahedron: (1) quality issues at all levels, (2) serious inequalities and regional disparities, (3) management/leadership problems, and (4) educational finance issues and how funds are spent. Two major tensions related to improving education are then discussed, namely, the competing influence of global/international and local indigenous forces and the complex challenges of determining educational priorities. HRH Princess Maha Chakri Sirindhorn stresses the importance of traditional holistic education. This chapter concludes with the presentation of alternative policy suggestions to rethink and improve Thai education. Among these suggestions are urgent policies to resolve the small school problem, to provide access to quality education for all, to reduce disparities and inequities at all levels of the system, to redesign teacher education, to improve teacher deployment practices, to produce a “new breed of teacher” and attract top talent to this profession, to increase community engagement with schools, to implement a more effective model of decentralization such as ABE, and to enhance effective R&D spending and related STEM education not only for the talented but for all. It is imperative that Thailand improve the quality of its educational system. If it does not, Thailand could be caught in a “middle-income trap” and surpassed by Asian neighbors on the rise such as Vietnam, India, and Myanmar (Burma).