I am using microsoft 2011 for mac.

When using Outlook, i am unable to send emails with attachments.

when trying to send the message i get a box saying "message could not be saved" and does not send or go to outbox/sent folder at all.

When i log into gmail and send it online it works fine so it is not the file size.
I have tried multiple options from these online forums that have not been successful

please help