Exemplary system 100 may additionally include a detection module 110 that may detect 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. Exemplary system 100 may also include a performance module 112 that may perform, as part of a data loss prevention program, a remedial action to prevent loss of the sensitive data based on both flagging the application and detecting that the application is requesting to output the data object in the format that obscures underlying content. The remedial action may include blocking the request to output the data object and/or tagging the data object with a tag that designates that the data object was created after the sensitive data was input to the application. Although illustrated as separate elements, one or more of modules 102 in