AutoMessage Not Sending Initial Email


I'm running Wordpress hosted on a Microsoft Azure website with a ClearDB MySQL backend with BuddyPress installed. I'm also using the Social theme with the AutoMessage plugin. When a new user signs up he is added to the queue however the message is never sent. If I wait 20 minutes or so the user eventually disappears from the queue but there is never a message sent. If I manually process the queue the email is sent correctly. It's a new site in pre-launch stage so there is little to no traffic after I've added a test user who ends up in the queue although I've tried ensuring there is some site traffic for 20 or so minutes after the user is added and the same thing happens. User disappears from the queue but no mail sent (unless I manually process before he disappears)

How can I troubleshoot and resolve this issue?

Thank you,