First email does not go through, but Reminder does

Hi, I am currently on the 14 day trial to see if Adobe Sign is the right product for me.  I was attempting to do some test runs by emailing out a document for signature. On all three attempts, the first Send for Signature email never appears in the recipient's inbox or spam, even after adding the email address to the contact.  However, the "Reminder" email sent appears without any issue.

Is this a known problem? Will we always have to send a reminder email for any of our documents to get sent out?