Prior to downloading Office 365 our Quickbooks POS system created purchase orders, converted them to pdf's which then opened in our Windows Live 2011 email for sending.  

I've now set up Outlook as our default email. (Connected to our gmail account via imap)  While our POS still creates the Purchase Order pdf and opens up the Outlook email template, when we send, it stays stuck in the outbox.  The pdf attachment is only 12KB, so I don't think size is the issue.  

I notice the outbox is in our personal folder, not our gmail folder.  Could that be part of the problem and if so, how do I fix that?  Thanks.