Automailer Frequency - Maybe Not

OK, I have the Automailer enabled with a frequency of weekly. I subscribed myself so I could monitor how this all works. I received an email immediately after subscribing, which was unexpected but fine. It has now been almost two weeks and I have not received ANY additional emails. In that time I have added two new posts.

How is this working for everyone? Is there something I need to do?
I was hoping this could work automatically while I build the site and not need to get going on MailChimp with my own schedule of subscriber emails.