Multiple E-Mail Certificates / E-Mails signed with wrong certificate RRS feed

  • Question

  • Hey there,

    hope you all are doing well. I have an awefull Problem with outlook, using SMIME for E-Mail signing and encryption.

    In my Oultook 2016 i have multiple mail accounts (private, business, university. For two of them (private & business), i am using SMIME for signing and encryption. I do not sign or encrypt all my e-mails, because then i would always get an error that there is no valid certificate when i am using an e-mail address i do not have a valid certificate for.

    So... When i sign an e-mail with the certificate, it happens from time to time that the e-mail is signed with the wrong certificate. Why the heck is this happening?

    So what i do is the following:

    1. I write an e-mail
    2. I hit the "sign" button
    3. A window with a Button (about 400 pixels wide) and just a key symbol appears and asks if i want to grant access to the certificate to sign this e-mail. I hit this Button
    4. Now it takes some time (about 15 seconds) until the e-mail gets sent.
    5. when i check my outbox I see, that the E-Mail - sent from my business account - is signed with the certificate of my private mail adress. As a result, my customers are not able to open the Mail because of an invalid certificate...

    What do i have to do to have always the correct certificate used? Its extremely disconcerting when you sent to your customer as an IT-Professional and it is signed by a wrong certificate...

    Sadly i have no idea how to fix this. Outlook seems not to be made for SMIME or using multiple profiles... Very sad...

    Hope you can help me with that problem. :)

    Thanks and Greetings from Germany.

    Monday, October 24, 2016 4:28 PM


  • Hi,

    In Outlook, please check the following settings:

    1. Go to File > Options > Trust Center > Trust Center Settings > E-mail Security.
    2. Click Settings to open the Change Security Settings window.
    3. Make sure you have created two security settings for your private account and business account respectively.

    If your settings are correct but the issue persists, please click Delete to remove all Security settings, restart Outlook then add the security settings back for your account to have a try.


    Winnie Liang

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    Tuesday, October 25, 2016 11:03 AM