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Systematic investigation of annealing behavior of drawn PMMA fibers was performed. Dynamics of annealing process were measured under different environmental conditions by fiber longitudinal shrinkage monitoring. Process was found to follow stretched exponential decay function indicating heterogeneous nature of underlying molecular dynamics. Consequences of fiber annealing for climatic stability of polymer optical fiber-based sensors are discussed, emphasizing importance of fiber controlled post-fabrication annealing. Dependence of induced fiber shrinkage on annealing time, temperature and fiber drawing conditions is investigated and interpreted. In addition, strong influence of humidity on annealing process was observed, which was not recognized in previous studies. This further highlights role of fiber post-fabrication thermal treatment with respect to intended operating conditions.