Here is the situation I’m working through. I have setup a Windows Server 2012 R2 Essentials server that is integrated with my Office 365 subscription. I have a multifunction device (Xerox 7545) that I need to configure the scan to email functionality. I configured an SMTP relay via IIS on my server. I have configured my Xerox to use the SMTP relay. This is all working. When I run the test SMTP settings, I receive my email as expected. However, when I try to do the scan to email, I don’t get my scanned document. I have called Xerox support and they mentioned that messages with attachments are getting dropped. Where do I allow messages with attachments to be emailed? Is this on the IIS SMTP relay or on a setting on Office 365 itself? As always, any help would be appreciated.