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Outlook Signing/Encryption Issues

    Question

  • Hoping someone can help me with 2 issues: 

    1. If I do not have my smart card in, Outlook will still send a signed message that people cannot open.  Other machines will prompt for a smart card and not allow the message to be sent. 

    2. My Trust Center does not show AES256 (or any AES options) for the encryption algorithm.  My only choices are RC4, RC2 and 3DES.  Other machines are showing the AES options. 

    Any thoughts? 
    Thanks

    Mark

    Friday, December 7, 2018 3:57 PM

All replies

  • Hi Mark,

    >> 1. If I do not have my smart card in, Outlook will still send a signed message that people cannot open.  Other machines will prompt for a smart card and not allow the message to be sent. 

    When do the other machines get the prompt? Then moment they click the "Send" tab?

    Please go to File > Options > Trust Center > Trust Center Settings... > Email Security, check if there are any difference on the settings between the problematic machine and the normal ones.

    Then sorry but we usually only discuss one question in one thread. For your second question, it is recommended to open a new thread in order to avoid confusion and keep track of troubleshooting steps.

    Regards,

    Yuki Sun


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    Monday, December 10, 2018 10:20 AM
    Moderator
  • Thanks - 

    Machines look identical in the trust settings, OS, etc...  Not sure what to look at from here.  We have even compared a few registry settings w/o luck. 

    Any thoughts?

    Mark

    Monday, December 10, 2018 2:33 PM
  • Thanks - 

    Machines look identical in the trust settings, OS, etc...  Not sure what to look at from here.  We have even compared a few registry settings w/o luck. 

    Any thoughts?

    Mark

    Hi Mark,

    As we have mentioned previously, did the users get the prompt the moment they click the "Send" tab? 

    Regards,

    Yuki Sun


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Thursday, December 13, 2018 10:38 AM
    Moderator
  • Yuki - 

    No, users do not get a prompt what so ever for a smart card or pin.  The message just gets sent.  Obviously with a signing and/or encryption error on the other end since the private key was not accessed. 

    Mark

    Thursday, December 13, 2018 6:09 PM
  • Yuki - 

    No, users do not get a prompt what so ever for a smart card or pin.  The message just gets sent.  Obviously with a signing and/or encryption error on the other end since the private key was not accessed. 

    Mark

    What if testing on your machine with the other users account to check the result?

    Regards,

    Yuki Sun


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Monday, December 17, 2018 11:50 AM
    Moderator