A client computer extracts contextual information associated with a file that is created. The client computer generates scores for the file by utilizing the contextual information that is extracted. The client computer assigns a value to the file, based on an aggregation of the scores that are generated. The client computer monitors activities on the client computer, wherein the activities trigger an event on the client computer. The client computer determines whether the event is in violation of one or more computer security policies on a server computer, wherein the one or more computer security policies require work-related files to be deleted or encrypted. The client computer classifies the file as personal data or work-related business data. The client computer secures the file, if the file is classified as work-related business data.