A system and method automatically rescales an electronic message having one or more associated content. When the electronic message is generated and the associated content connected to the message, an agent of the electronic message application checks predefined settings/configurations of the message client. The sender's e-mail client checks a plurality of conditions, such as, the condition of the network, the type of network, the status or capacity of the receiving inbox of an intended recipient client, and the geographic destination of the message. Based on these dynamic content rescale settings, the sender's client dynamically and optimally rescales the associated content before forwarding the electronic message with the rescaled content to the recipient client. Rescaling of the associated content may be performed by the message exchange server or the recipient client. The recipient client may later request and receive a copy of the associated content without rescaling.