Problem sending signed/encrypted email in Outlook 2010 RRS feed

  • Question

  • Hi,

    I'm trying to setup email encryption with Outlook 2010. I have a certificate of the person I'm trying to communicate securely with, in .cer format. I've created an address book entry with his email and certificate in it. I've also created my own certificate and sent it to him in .cer format. In addition, I've added myself in the address book with my email and certificate in the entry.

    I'm able to send signed/encrypted emails to myself. However, when I try to do the same to him, I get a popup dialog that says:

    Microsoft LDAP Directory - Bad search filter 

    Once I click on the OK button, this popup dialog shows up 

    Encryption Problems - Microsoft Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities:


    Continue will encrypt and send the message but the listed recipients may not be able to read it.

    The "Continue" button is greyed out. 

    What am I doing wrong? Thanks! 

    Tuesday, May 19, 2015 9:18 AM


  • Hi,

    As per the information and details provided by you, to solve this issue, please follow these steps: -

    To show the continue button, add the SecurityAlwaysShowButtons value to the registry. 

    Exit Outlook

    Start Registry Editor.

    In Outlook 2010

    In the Edit > New > DWORD Value.

    Type SecurityAlwaysShowButtons > Enter.

    Right click SecurityAlwaysShowButtons > Modify.

    In the Value data > type 1 > OK.

    Exit Registry Editor.

    Typically, before the Sign and Encrypt Ribbon controls are available, you must specify which certificates are to be used for signing and for encrypting.

    I hope this information will be helpful for you.

    Thanks and regards

    Tuesday, May 19, 2015 12:31 PM