A computer-implemented system and method for providing context-sensitive sidebar window display on an electronic desktop is provided. A document that includes digital data is maintained in electronic storage. The document is operated upon through an application window generated by an application program on an electronic desktop. A sidebar window is initially generated. Contextual information relevant to the document is determined. Part of the contextual information to present is selected based on a current state of the document in the application window. The selected part of the contextual information is presented in the sidebar window positioned visually adjacent to the application window. The contextual information presented in and the positioning of the sidebar window is continually updated in step with the current state of the document and the application window.