Abstract: A handheld portable communications terminal includes a freehand input device, such as a touch screen or a digital pen, and plural messaging applications. One messaging application allows a user to input a drawing using the freehand input device, and produces drawing data in a standard or commonly-used format representative of the drawing. A second messaging application, selected by the first messaging application, sends the drawing data in a message in a standard or commonly-used format (e.g. SMS, MMS, IM, email). This allows the drawing to be reproduced by a receiving terminal equipped with a standard or common messaging application. The first messaging application provides for the immediate entry of a drawing using a freehand input device in response to the opening of the messaging application. It provides means to allow a recipient address to be entered or selected in response to an input indicating the completion of content entry.