none
Outlook 2016 x64 - cannot send digitally signed message (S/MIME)

    Question

  • After Office365 installation (2016) and Outlook configuration, all things seems to be fine, but when trying to send digitally signed message to anyone (we have our internal certificates from internal MS CA) following message appears: "A required action was not successful because of an unspecified error." and message is not sent.

    When receiving signed message from other users, everything is O.K.. I am able to read it. The same thing with messages encryption. I can send or receive encrypted mesages. Only cannot sign any message.

    Deinstalling Office365 x64 and installing 32bit version solved problem. The same experience with "pure" Office 2016 Pro package. 32bit without problém and with x64 same error signing message. 

    Is there some bug in x64 version?

    Office is installed on Windows 8.1 or Windows 10. Tried with more mailboxes and PCs.

    It is installation package from Office365 portal (or Office 2016 Pro from MSDN .iso file) but used with on-premise Exchange mailbox.

    I found possible solution (https://thecomputerperson.wordpress.com/2015/07/29/outlook-2013-windows-10-bug-a-required-action-was-not-successful-because-of-an-unspecified-error/), but this does not solve my problem.

    Note:

    I reported that problem to Office365 forum first. They recommended to me post it to MS Office Community. They recommended to me ask in Exchange forum and I have last recommendation to ask in your forum :-).

    Tuesday, November 24, 2015 11:56 AM

Answers

  • Hi,

    Do you have the "Request S/MIME receipt for all S/MIME signed messages" option enabled in Trust Center > Email Security? If not, please try to enable the option and then check if this issue continues.

    Have you tried using cert from another cert provider to see if this issue continues?

    In addition, please have a look at the following article:

    http://social.technet.microsoft.com/wiki/contents/articles/32288.windows-enforcement-of-authenticode-code-signing-and-timestamping.aspx

    Seems that we are doing some changes in next months with code signing. Not sure if it has something to do with this issue, but it could be some changes/limitations that we already did in the product to prepare for this change.

    Regards,

    Steve Fan
    TechNet Community Support


    Please mark the reply as an answer if you find it is helpful.

    If you have feedback for TechNet Support, contact tnmff@microsoft.com.
    • Marked as answer by yirka1 Wednesday, November 25, 2015 10:59 AM
    Wednesday, November 25, 2015 2:26 AM
    Moderator

All replies

  • Hi,

    Do you have the "Request S/MIME receipt for all S/MIME signed messages" option enabled in Trust Center > Email Security? If not, please try to enable the option and then check if this issue continues.

    Have you tried using cert from another cert provider to see if this issue continues?

    In addition, please have a look at the following article:

    http://social.technet.microsoft.com/wiki/contents/articles/32288.windows-enforcement-of-authenticode-code-signing-and-timestamping.aspx

    Seems that we are doing some changes in next months with code signing. Not sure if it has something to do with this issue, but it could be some changes/limitations that we already did in the product to prepare for this change.

    Regards,

    Steve Fan
    TechNet Community Support


    Please mark the reply as an answer if you find it is helpful.

    If you have feedback for TechNet Support, contact tnmff@microsoft.com.
    • Marked as answer by yirka1 Wednesday, November 25, 2015 10:59 AM
    Wednesday, November 25, 2015 2:26 AM
    Moderator
  • Thanks for good advice.

    Checked "Request S/MIME receipt for all S/MIME signed messages" option and able to send signed message.

    We will concentrate on use other certificates, because one colleague has cert from public CA and he does not have this problem. But change of internal PKI infrastruture is more complex project.

    Apply only to x64 edition of Office 2016. There os no such problem in 32bit edition.


    • Edited by yirka1 Wednesday, November 25, 2015 11:00 AM
    Wednesday, November 25, 2015 10:40 AM
  • Sadly, it is not working with me still got:
    A required action was not successful because of unspecified error.

    SFC /scannow - throws no errors

    Checked "Request S/MIME receipt for all S/MIME signed messages" option

    Windows 10 Enterprise

    Office 2016 Professional x64 16.0.6366.2036

    Signature  used has no problem whatsoever if I'm using x86 version of Office 2016

    Any suggestions are welcome!

    UPDATE: Finally after 23.02.2016 update Office 2016 Professional x64 16.0.6568.2025 Outlook is able to send signed Mails again!


    • Edited by Savcho Savchev Tuesday, February 23, 2016 6:40 AM Issue fixed
    Wednesday, January 06, 2016 5:35 PM
  • Enabling "Request S/MIME receipt for all S/MIME signed messages" option fixed this problem for me also. I am running the 64-bit version of Office 2016 for Windows on Windows 10 Enterprise Current Branch. Running "SFC /scannow" did not fix my problem.
    • Edited by JCATX Tuesday, February 09, 2016 9:49 PM
    Tuesday, February 09, 2016 9:32 PM