But that's just it. Being that it's 2012, the e-mail client should be smart enough to do this. I should be able to attach a large attachment to an e-mail (since

But that's just it. Being that it's 2012, the e-mail client should be smart enough to do this. I should be able to attach a large attachment to an e-mail (since that's the logical place to make the association), and then, depending on the attachment size, the e-mail client should automatically move it to Dropbox or some other service and translate the attachment into a link for me. The difference between the your first approach and the second is that yours requires a behavioral change. The second approach does not. Put another way, it is often easier to change the situation (by making it the path of least resistance) than the person when you want someone to do something else. It seems like some of this is already in the works, fortunately: http://www.ghacks.net/2012/02/15/thunderbird-to-get-dropbox-and-file-hosting-integration/ http://www.ghacks.net/2012/02/15/thunderbird-to-get-dropbox-... Maybe it already exists in certain clients (Exchange and Outlook?) and I just haven't looked hard enough.