Can't send to recipients in Office 365 from on premises

I have a test recipient in Office 365 that can send email to me (my mailbox is on premises) but I cannot send emails to it. All of the emails get caught on the edge transport with a loopback error. 

I only have the 2 default send connectors configured when I configured EdgeSync (ADsite to internet and Internet to ADsite). Do i need to specify something on these connectors?