Help with scan to email configuration in Server 2012 Essentials and Office 365

Hello Experts,

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.

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Vasil Michev (MVP)Commented:
Just in case, make sure to verify the correct setup of the SMTP relay with this article (i.e. TLS is mandatory):

Review the IIS SMTP logs and check if there is something wrong in there. You can also run a message trace on O365 to make sure the messages are not being dropped there. But I vaguely remember others complaining about the same issue with Xerox devices, unfortunately I'm not able to find the thread...

If I remember correctly, they updated the requirements and then it stopped working. I believe the device needs to support at least TLS 1.2 for it to work. Make sure to check the IIS logs :)

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