Looks to be an older conversation, and my situation is currently Windows-based rather than Mac, but this sounds a lot like the problem I just encountered today. I'm a premium member, so I'm thinking that eliminates any account-type-based restrictions. Tried to create a very basic note today, in which I wanted to put 2 Word documents. The snippet would show that the note had 2 attachments but I couldn't find anything in the note itself. Tried several times, recreating the note, rebooting the computer, etc. A couple attempts got me nowhere. Finally got to where I could attach (and SEE) one of the files. Retried/recreated some more, and would get that same one "successfully" but the other was attaching as a .bin file and wouldn't let me open it. Of course, Murphy's law, just tried again in the midst of typing this to confirm what it was showing me and the 2nd one finally seemed to attach itself correctly. Definitely buggy IMO and quite frustrating. First time I've encountered this but I don't try to use Word all that often with Evernote. Would love to know if there's a trick or inherent limitation with this!