A mobile communication device may operate with a number of different applications, each having different file types associated therewith. A file analyzer receives data files and analyzes the files to identify a content type and thereafter associates the identified file with the appropriate application or applications. The received data files may be delivered through a wired connection, a wireless connection, or through the introduction of a memory device, such as a removable storage device, to the mobile communication device. The file analyzer may provide the appropriate notification or indication of association or association to the application associated with the identified content type and may further provide user notification of a newly delivered file. The files may be data files, such as text or multimedia files such as audio and/or video files. Files that are incompatible with the wireless communication device may be rejected by the file analyzer or left to the user to make a manual determination of content type and association with the appropriate application.