In one embodiment, one or more of modules 102 from FIG. 1 may, when executed by at least one processor of computing device 202 and/or server 206, enable computing device 202 and/or server 206 to prevent data loss. For example, and as will be described in greater detail below, monitoring module 104 may monitor, through at least one filter (such as a network filter 242, a clipboard filter 240, inter-process filter 246, and/or a file system filter 244), data 232 input to an application 230 during execution. Scanning module 106 may scan, through a data loss prevention scanner, data 232 input to application 230 to detect whether data 232 includes sensitive data 234 that is protected by a data loss prevention policy. Flagging module 108 may flag, based on the scanning, application 230 as having accessed sensitive data 234 that is protected by the data loss prevention policy. Detection module 110 may detect, after flagging module 108 flags application 230, that application 230 is requesting to output a data object 212 in a format that obscures underlying content such that the data loss prevention scanner is prevented from scanning data object 212 to determine whether the underlying content includes sensitive data 234. Performance module 112 may perform, as part of a data loss prevention program, a remedial action 214 to prevent loss of sensitive data 234 based on both flagging application 230 and detecting that application 230 is requesting to output data object 212 in the format that obscures underlying content. System 200 may also include an application 250 that may correspond to a target application receiving data object 212 from application 230 as a source application.