Email Attachments not working

[lostiris]

First this is on a Mac computer, I have tried it on a laptop and it works, I have tried it on a PC and it works, but when I try it on the big Mac it does not work. When I try to send an email with an attachment that I recently edited, the most recent version, or at least the ones from the today/ the current day do not show up. But when I go looking for it in the Finder I see it. This is for Gmail on Google Chrome.