The invention provides a method and system for delivering relatively large documents (such as for example media documents) with reduced use of time and other resources. Relatively large documents sent by a sender to a recipient in an email message are delivered separately from the email message, asynchronously from delivery of the email message or its presentation to the recipient, and using an out-of-band technique separate from email message delivery. This provides for relatively rapid and reliable delivery of the email message, separate reliable delivery of the media document, and presentation of the media document to the recipient without further sending delay. Pre-probing of destination devices may occur to determine a preferred set of characteristics to manage delivery.