Sending Emails is Intermittent

I have a workflow that sends an email to our vendor when a new order is uploaded. The email address that it sends to is to pull a record from a table on the database.

The weirdest thing is that the email is successful when I use a certain email addresses as the recipient but not others. I can’t seem figure out the rhyme or reason for this and it seems to be very inconsistent.

Hard to say from the images here, my first guess would be that it is something to do with your privacy rules. Where is the To email coming from?

The to email is hard coded.