Techniques for disambiguating at least one text segment from at least one acoustically similar word and/or phrase. The techniques include identifying at least one text segment, in a textual representation having a plurality of text segments, having at least one acoustically similar word and/or phrase which has a different spelling, annotating the textual representation with disambiguating information to help disambiguate the at least one text segment from the at least one acoustically similar word and/or phrase, and synthesizing a speech signal, at least in part, by performing text-to-speech synthesis on at least a portion of the textual representation that includes the at least one text segment, wherein the speech signal includes speech corresponding to the disambiguating information located proximate the portion of the speech signal corresponding to the at least one text segment.