Described is a technology by which synthesized speech generated from text is evaluated against a prosody model (trained offline) to determine whether the speech will sound unnatural. If so, the speech is regenerated with modified data. The evaluation and regeneration may be iterative until deemed natural sounding. For example, text is built into a lattice that is then (e.g., Viterbi) searched to find a best path. The sections (e.g., units) of data on the path are evaluated via a prosody model. If the evaluation deems a section to correspond to unnatural prosody, that section is replaced, e.g., by modifying/pruning the lattice and re-performing the search. Replacement may be iterative until all sections pass the evaluation. Unnatural prosody detection may be biased such that during evaluation, unnatural prosody is falsely detected at a higher rate relative to a rate at which unnatural prosody is missed.