A system and method of contextually converting a media file into an electronic document allows the user to generate an interactive transcription from the audio portion of a provided media file, which subsequently connects to the media file such that the user can play the media file from a selected transcribed word. Screenshots from video files may also be appended to the electronic document at transitions in video content and subsequently matched to appropriate transcribed words within the generated document. The system implementing the method includes a user account managed by at least one remote server, wherein the user account is associated with a corresponding personal computing (PC) device. This arrangement enables each user to interact with the at least one remote server using the corresponding PC device. The method follows an overall process in order to generate an electronic document with timestamped transcriptions.