At step 308 in FIG. 3, one or more of the systems described herein may detect, after flagging the application, that the application is requesting to output a data object in a format that obscures underlying content such that the data loss prevention scanner is prevented from scanning the data object to determine whether the underlying content includes the sensitive data. For example, detection module 110 may, as part of server 206 in FIG. 2, detect, after flagging application 230, that application 230 is requesting to output data object 212 in a format that obscures underlying content such that scanning module 106 is prevented from scanning data 232 to determine whether the underlying content includes sensitive data 234.