A dynamic icon overlay system of a present invention embodiment dynamically generates icon overlays to be applied to a primary file icon of a target file. The icon overlays convey information regarding the target file and are relevant to an end user. The icon overlay system determines icon overlays to be applied to the primary file icon based on attributes associated with an end user of the target file that are correlated with attributes of the target file itself. The system applies the icon overlay to the primary icon and displays the primary icon with the applied icon overlay at an end user system. The applied icon overlay for the same target file may vary for different end users based on user attributes.