Contextually placed chat-like annotations in an electronic record. Users can input successive time-stamped annotations at a selected location in an electronic record. The annotations are displayed chronologically in a discussion window, which is customizable by color, style, and location. The discussion window styles minimize clutter and distraction, thus providing for more effective review and collaboration. The discussion location is indicated by a discussion point icon, and can be displayed in a window of fixed size with scrolling capability. A user can email the discussion window content to other users and request an alert, notifying the user of successive annotations. An annotation engine can reside on a server and receives user input and performs functionality related to the annotations. The electronic record can reside on the server and is repeatedly updated to reflect current content relating to the electronic record and annotations.