It would be helpful if there could a minimum size the attachment needs to be prior to the Outlook plug-in utilizing the transfer server for sending the file. If I want to email a 50kb file to a coworker in the office, it doesnt need to be uploaded to the server. But if we (the IT department) could set it so that someone attaches a file over a certain size, that the plug-in will then kick in to transfer the attachment to the server. That would be a major improvement to the Outlook plug-in, without it, it is almost more trouble than its worth to use within our office. If you are looking for an example on how the functionality of this works, the YouSendIt plug-in has this feature. Thanks!