Technology can fix this! It was never the users problem to begin with... MAX_ATTACH = 50 * 1024 #50 kb def minimize_size(msg): if size(msg['a

Technology can fix this! It was never the users problem to begin with... MAX_ATTACH = 50 * 1024 #50 kb def minimize_size(msg): if size(msg['attachment']) > MAX_ATTACH: upload attachment to s3 like storage insert link into email body return msg It obviously needs fleshed out (I bet it ends up around 20 lines of python after everything is said and done). But seriously, the fact that your users would ever even need to think about this is just wrong.