Hello,
Thank you for reaching out to SmarterTools. My name is Zach I will be helping you with this question.
Most likely what is happening here is that the sender is failing DKIM or SPF when this happens the trusted sender status is revoked. The reason for this is that if it fails those checks it could be someone impersonating that email.
To get around this you could create a custom spam check at the system level that looks at the To: header for an email from that user then gives it a score of -99.
Heres an example.
Please let me know if you have any questions.
Kind Regards,
Zach Sylvester
Software Developer
SmarterTools Inc.
www.smartertools.com