Error - Forwarding mail with digital sign as a attachment RRS feed

  • Question

  • Good day.

    We've discovered this strange error on several PC's: when we try to forward any mail signing with digital sign to another user - new mail is creating and mail with digital sign are included in new mail as attachment (!).

    This problem appears only with digital signed mail, ordinary mails are forwarding correctly. We've checked any GPO and outlook/mail settings, but nothing.......Client is Outlook 2010.

    Any ideas?


    Wednesday, May 20, 2015 1:44 PM

All replies

  • Do the users who are attempting to forward the email have X.509 certificates?  As I recall, when you forward a signed email, Outlook will automatically sign the forwarded message.  If it can't (if the user has no X.509 certificate), it will attach the original signed message so the end-recipient will see the original message was also signed.

    I'll add, it's been a long time since I worked with SMIME messages in Outlook so things may have changed.

    Will Martin ...
    -join ('77696c6c406d617274696e2d66616d696c6965732e6f7267' -split '(?<=\G.{2})' | ? { $_ } | % { [char][int]"0x$_" })

    Wednesday, May 20, 2015 1:58 PM
  • We didn't detect any regularity, because both types users (who has got X.509 certificate and who hasn't) are involved this problem....

    Wednesday, May 20, 2015 2:21 PM
  • Hello,

    You may need to check the message tracking, protocol logging to see if this changes happens on your Exchange Server or the remote Exchange Server.


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    Simon Wu
    TechNet Community Support

    Tuesday, June 16, 2015 6:11 AM
  • It's Outlook that's doing this - Exchange isn't going to take a message and encapsulate it once Outlook sends it.  Exchange takes what Outlook gives it and passes it along.

    Will Martin ...
    -join ('77696c6c406d617274696e2d66616d696c6965732e6f7267' -split '(?<=\G.{2})' | ? { $_ } | % { [char][int]"0x$_" })

    Tuesday, June 16, 2015 11:45 AM