An automated system and method for transcription of a dictation presents a transcription exercise to a student that allows continuous student keyboarding of text while providing real time feedback of correct, incorrect, and misplaced characters as well as visually pointing out the location of missing letters and missing words. The real time designation is shown using differences in typeface style or color and using a scoring system that factors in substantially all keystrokes. Not only is final correctness assessed, but also the difficulty in getting to the final state of correctness is assessed.