A computer-implemented method for increasing compliance with data loss prevention policies may include (1) identifying a file that is subject to a data loss prevention policy, (2) determining a classification of the file according to the data loss prevention policy, (3) identifying a graphical user interface that is configured to display a representation of the file, and (4) enhancing the representation of the file within the graphical user interface with a visual indication of the classification of the file according to the data loss prevention policy. Various other methods, systems, and computer-readable media are also disclosed.