Outlook 2016 S/MIME Hangup

Simeon Steffen 1 Reputation point

Hello together,

i have an strange problem with Office 2016 Pro Plus on an domain joined terminalserver (Windows Server 2012r2).

When we try to send mails with S/MIME signature or S/MIME encryption Outlook hang up and must be killed with taskmanager.
When we receive encrypted messages and try to open, the last focused mail ist displayed no matter what mail we choose after.
Options menu works but we cant write new mails or read other than last focused - Outlook must killed with task manager.

After repairing Outlook, the problem is gone, all works fine for 12-24 hours than the behavior happend again and we have to repair.

For the moment i repair outlook every morning automatic with a script - but this cant be a solution

Any idea how i get rid of this problem?

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Jade Liang-MSFT 9,946 Reputation points Microsoft Employee

    Hi @Simeon Steffen ,

    i have an strange problem with Office 2016 Pro Plus on an domain joined terminalserver (Windows Server 2012r2).

    Did this issue occur on any specific users/ clients or all users in your organization? And could those clients that not on domain joined terminal server work normally?
    If it occurred on any specific clients only, please kindly check if there are any differences between this clients and others(such as client version, add-ins or other anti-virus programs)

    According to your description, your Outlook client seems to be corrupted when you send / receive a message with your S/MIME certificate , in the point of Outlook, what's the version of your Outlook 2016(File>Office account>About Outlook), please first ensure that you have installed the latest update of Outlook.

    Considering any third-party add-ins or anti-virus programs may also cause it, it's suggested to close other programs and test in Outlook safe mode to check if the issue has any difference(Windows + R > type "Outlook.exe /safe"> enter)

    If the issue still exists, in order to confirm if it's related to your certificate itself, if it's possible, please try to switch to other certificate or use this certificate on other client for testing.

    Also, if the issue occurred on those clients joined terminal server only, it may be more related to terminal server, it's recommended to post your issue in terminal-server related forum to get more targeted suggestions.

    If the response is helpful, please click "Accept Answer" and upvote it.
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