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Unable to open Encrypted Emails on Outlook 365 Desktop App (OWA Disabled)

Anonymous
2024-08-02T18:34:12+00:00

We are having an issue with opening Encrypted Emails in our Office 365 environment, specially on the Outlook Desktop app. We have several encrypted email examples given to us from other clients and we have one machine than can open them fine, and then one machine that cannot. We have OWA disabled due to it's security risk we have ran into.

These are both Win 11 machines, running same version of Outlook 17726.20160. We have done all the restarts of the application and re-install all 365 apps.

From what I can tell, there is nothing different between these machines that we cannot find. The machine doesn't work will fail when pulling up the encrypted email and advise to follow a link to OWA to view it, but we are keeping OWA disabled.

Any advise to see what could be different between these two machines that will allow one to view encrypted emails just fine and the other not will be appreciated.

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  1. Anonymous
    2024-08-02T21:16:55+00:00

    Thank you for you reply.

    We have done all the requested tasks and no change has occurred. We are still unable to see encrypted emails on the specific machine. I did not see any discrepancies between the two devices.

    Why would your next advise be to take a look at?

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  2. Anonymous
    2024-08-02T20:38:53+00:00

    Dear Kirkland Hoult,

    Good day!

    Thank you for reaching out with your concern about opening encrypted emails in the Outlook Desktop app within your Office 365 environment. We understand the importance of being able to access encrypted emails efficiently and securely.

    To address this issue, we recommend checking and comparing the following configurations and settings on both machines:

    Review Outlook Profile:

    • Sometimes, the Outlook profile can be corrupted. Try creating a new Outlook profile on the problematic machine:
      • Go to Control Panel > Mail > Show Profiles.
      • Click Add to create a new profile and set it as the default.

    create a new Outlook profile

    Run Outlook in Safe Mode to rule out any issue caused by add-ins:

    • Start Outlook in Safe Mode to see if the issue persists. This can help determine if the problem is related to add-ins or settings:
    • Hold the Ctrl key while opening Outlook, or run outlook.exe /safe from the Run dialog.

    Outlook online repair:

    • If the issue continues, perform a repair on the Office installation:
      • Go to Control Panel > Programs > Programs and Features.
      • Find Microsoft 365, click on it, and select Change. Choose Quick Repair and follow the prompts.

    Certificates and Encryption Settings:

    • Check if both machines have the necessary certificates installed and trusted. Sometimes, missing or untrusted certificates can cause issues with opening encrypted emails.
    • Open Outlook and go to File > Options > Trust Center > Trust Center Settings > Email Security. Ensure that the same settings are applied on both machines.

    By following these steps, you should be able to identify and resolve the discrepancy between the two machines. If the issue persists, please let us know, and we can explore further troubleshooting steps.

    Please understand that our initial response may not always resolve the issue immediately. However, with your help and more detailed information, we can work together to find a solution.

    Appreciate your kind understanding. Have a great day!

    Sincerely,

    Microsoft Community Moderator

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  3. Anonymous
    2024-08-06T15:54:00+00:00

    Hello Kirkland Hoult

    Thank you for your clarification. Sorry for the late reply.

    In this case, I'd recommend creating a ticket with our support team so that a support agent can connect with you to check this remotely. Get support - Microsoft 365 admin | Microsoft Learn They will be able to collect the necessary logs and work with you and involve the backend team if needed. Please create a ticket and provide as much detail as possible about the issue you're experiencing and steps you tried.

    In the meantime, I would also like to invite community members and MVPs in the forum to share their knowledge or any workaround and insight on this topic.

    Thanks for your precious time and your understanding would be highly appreciated.

    Sincerely,

    Microsoft Community Moderator

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