Abstract: A system for analyzing and prescribing content changes to achieve target readability level evaluates a readability score for a file at least at a whole document level and a sentence level based on a designated readability index; identifies one or more sentences that contribute to the file having the whole document level readability score outside a desired readability score of the readability index; provides a visual indicator for each of the identified one or more sentences; and re-evaluating the readability score for the file at the whole document level upon at least one of the identified one or more sentences being changed.