So as I run my own dedicated server I have complete control over spam and how filters are implemented. Now, to help decrease spam I had enabled the check for email addresses by actually contacting the sending server to see if the sending address is valid. For whatever reason, jpalermo doesn't seem to be a valid email address 🙁 Not sure why, but once I disabled this check, the emails started coming through again.
So that seems to be the issue. The email address that the board is sending from doesn't actually seem to be a real address (or not by my server's checking). Something for someone to look into 😉