One of my colleagues is having the same problem. We recently upgraded to the Cloud (Jive 7) and users with PCs can upload up to 30 attachments (using the "Write a doc" feature), he has a mac and is having issues uploading more than one file at a time. One file is allowed for attachment, however, the system rejects attempts to create an additional attachment to the same doc. Is anyone else having this issue and if so, is it a known bug?
I just wanted to confirm here, are you using the document upload in Producteev, or in Jive itself?