A communication system is provided that enables automated retrieval of caller ID picture information and association with contact information, while still allowing security control over information or images that are sent to the requesting device. The communication system has a wireless device communicating with a picture server. The wireless device receives an incoming call with caller ID information, and determines if a picture is locally stored for the caller. If no picture is locally stored for the caller, then a request is made to retrieve a picture from the picture server. If the picture server has the requested picture, and the wireless device is authorized to receive the picture, then the picture is downloaded to the wireless device, where the picture is associated with contact information for the caller. The picture of the caller will then be automatically displayed when the caller places future calls.