Signed e-mail messages not sent as plain text with enterprise enforced e-mail "signature" RRS feed

  • Question

  • I have a digital certificate used for e-mail encryption/signing and using Outlook 2013 connect to my work Exchange server (I think 2010). I'm trying to send digitally signed, plain-text e-mails.

    I create a test e-mail with the following options under "Options/Security Properties":
    "Add digital signature to this message", and "Send this message as clear text signed"

    The e-mail was sent to myself and to my Gmail account. The unexpected result, shown in the screen capture below, is that in Outlook 2013, the message shows up as an attachment, and the only plain text is the automatically generated e-mail signature. If I think click on the attachment itself, you can see the message and that it's been "signed" by myself.

    [Edit: Cannot insert links or images until my "profile" has been verified...whatever that means, and no clear methodology to do so. I have to open up a separate window and search for it finding that following great thread - oh wait, I can't insert the thread either because I can't insert HTML links, lol. Anyway, I'll describe what would've been a simple screen capture:

    The message when displayed in Preview pane shows only the enterprise enforced e-mail signature. In the top, you can choose between "Message" or a picture of a signed e-mail with my subject heading. If you click on the signed e-mail icon, you would then see my entire signed e-mail (as a separate e-mail message) with an indication that it's been signed.]

    If I were to open this up in Gmail, I would see only the automatically generated e-mail signature and the smime.p7s attachment, befuddling most recipients.

    I suspect that the enterprise added signature (likely via Exchange server settings) is invalidating the e-mail signature and thus the original message is wrapped in smime.p7s and the plain text signature appended. This defeats the purpose of plain-text sending with digital signatures.

    Am I correct in this assumption or is Outlook 2013 having trouble sending plain-text signed e-mails? Unfortunately, I'm not the sysadmin for the Exchange server so I cannot test this theory. If I am correct, is there a work-around I can send to my IT folks to see if they can make the Exchange server compatible with plain-text digitally signed messages?



    Wednesday, January 29, 2014 10:03 PM