A new adamantane-based dicyanate ester has been synthesized. The kinetics of its thermal polymerization is studied by means of conventional and temperature-modulated differential scanning calorimetry. The kinetics is analyzed comprehensively by a combination of an advanced isoconversional and model-fitting method. Polymerization proceeds via transition from a kinetic- to diffusion-control regime, which becomes operative at the later stages of the process. The kinetically-controlled regime manifests itself as a quasi-one-step auto-catalytic reaction. A contribution of diffusion to the overall kinetic is accounted for by means of the Fournier model. The polymerization product possesses excellent thermal properties (the glass transition temperature of ∼370 °C and 5% mass loss temperature of ∼480 °C), which makes it a promising candidate for application in hot-section components for aerospace and military industry.