A text messaging system which converts at the sending device a detected URL in a text message to a representative image or other content and transmits the representative image (which represents the URL) to one or more messaging servers for delivery to a receiving device. In one embodiment, the messaging servers do not have access to clear text of either the representative image or the URL. In one embodiment, the retrieval occurs in response to a selection of a send command. Heuristics (such as rules) can be used to determine whether to convert a detected URL.