In some examples, flagging module 108 may flag application 230 by determining that the application has accessed a quantity of sensitive data. Moreover, flagging module 108 may also then determine that the quantity of sensitive data is greater than a threshold amount that defines a threshold beyond which the application is flagged. For example, the threshold may specify that the detection of any sensitive data may trigger the flagging of the application. In other words, a single hit that matches a single item of data that the application accessed to a single item of data that the data loss prevention system blacklists to protect from loss may trigger the flagging of the application (i.e., a single credit card number match). Alternatively, the threshold amount may define a larger amount of sensitive data beyond which the application is flagged, thereby providing the application with some tolerance and preventing an overly strict application of the data loss prevention policy. For example, flagging module 108 may require two, three, four, five, 10, 20, 50, 100, or any other arbitrary amount of sensitive data (e.g. in terms of hits) to be detected before flagging the application as having accessed sensitive data.