Fought this issue for a while, so wanted to report back the fix for my system.

Mine ended up being an Exchange-Authentication problem.. here's the Exchange Powershell script to fix it:

Get-ReceiveConnector "Local Relay" | Add-ADPermission -User "NT Authority\ANONYMOUS LOGON" -ExtendedRights "ms-Exch-SMTP-Accept-Any-Recipient"

And then just Restart Service "Microsoft Exchange Transport" to seal the deal.