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Encryption Issue with Outlook 2016 RRS feed

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    I have been directed to come to this board and ask my question.

    I currently use Outlook 2016 with multiple accounts (MS Exchange, IMAP and POP).  My computer OS is Win10pro.  Outlook came as part of the MS Office Suite Pro.  I run a standalone system that isn't part of any domain. 

    I have one account that is associated with a IdenTrust PKI Certificate.  With that account I am able to send and receive encrypted emails to government users that have a government issued CAC (military ID).  I'm having no problem with government users. 

    But  ... Interestingly enough, I am able to receive encrypted emails but am unable to reply with an encrypted email to users with an IdenTrust PKI Cert within the company.  The error that comes up is: "MS Outlook had problems encrypting this message because the following recipients had missing or invalid certificates, or conflicting or unsupported encryption capabilities".   The person's contact card (with the certs) has been added to my contacts list.  I have trusted their certificates.  I can receive encrypted from this person but am unable to reply with an encrypted email.  This has been a persistent issue for several months.

    I have searched the data base for anything of this nature but have been unable to find anything that helps.  Any help would be appreciated.

    Thanks.

    Tom

    Thursday, March 15, 2018 2:01 PM

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    Hi Tom,

    >>Interestingly enough, I am able to receive encrypted emails but am unable to reply with an encrypted email to users with an IdenTrust PKI Cert within the company.

    Can you send an encrypted email directly to the users? 

    When receiving encrypted emails, the email is encrypted using your public key, and you are using the your own private key to decrypt the message. However, when sending an encrypted email, you are using the recipient's public key to encrypt the message. If you don't have the recipient's public key or the public key has expired, you will see this error message. You may ask one recipient to publish the correct certificate to GAL and then try sending an encrypted message to the recipient again to see the result.

    Regards,
    Steve Fan

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    • Proposed as answer by Steve Fan Wednesday, March 21, 2018 10:09 AM
    Friday, March 16, 2018 9:23 AM
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    Hi Tom,

    Just checking in to see if the information was helpful. Please let us know if you would like further assistance.

    Best Regards,

    Steve Fan

    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.

    Wednesday, March 21, 2018 10:09 AM