The disclosure is directed to a document management system having a label management user interface. The document management system may be configured to display document content in either a document view mode or a document edit mode in which document content is displayed in a content panel of the graphical user interface. When in the document view mode and an authenticated user has edit permissions with respect to a current document, the graphical user interface is configured to display a label management user interface including an array of user-selectable label graphical objects and a list of recommended labels selected in accordance with a label score that is based on a set of multiple heuristics. Using the label management user interface, the user may transition from recommended label operations to a dynamic search operation and to a custom label creation operation without leaving the context of the current interface.