Within a system comprising a processor and a memory, a method of sending an attachment of a first electronic mail (email) to a recipient. The method includes receiving the first email addressed to the recipient and, via the processor, determining whether a volume of data contained in the recipient's electronic mailbox has reached a threshold level. When the volume of data has reached the threshold level, via the processor, establishment of an instant messaging session with an instant messaging client associated with the recipient can be initiated. The attachment can be caused to be attached to an instant message. Sending of the instant message to the instant messaging client associated with the recipient can be initiated.