This article reviews both time-honored and most recent studies of the mechanisms and kinetics of cyanate esters polymerization. Different types of processes, including catalytic, non-catalytic, bulk, solution, and nanoconfined ones are covered. The mechanistic and empirical models suitable for describing the kinetic and diffusion regimes of polymerization are discussed at length. Recent advances in methodology of the analysis of multistep polymerization reactions by means of model-fitting and isoconversional techniques are considered as applied to cyanate esters. The importance of the calorimetric measurements in polymerization studies is emphasized.