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If we create a transport rule to block all emails sending out with .doc attachment, it seems that the rule won't work on email which is signed with S/MIME cert.

The email sending out is just signed, not encrypted. so I expect that the transport rule should still work on the email. Is there anyway to get around this?

thanks SC

  • what's your detailed rule? please show it to us. – Niko.Cheng Nov 30 '18 at 10:17
  • " Apple rule to messages from 'xxx@xxx.com' and when any attachment file name matches '.docx' send 'DOCX cannot be sent' to sender with '5.7.1' " – Sun Cleverland Dec 4 '18 at 9:22

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