Issue with Certificate Selection in Outlook 2019 for S/MIME Encryption

Question

Hello everyone,

I'm facing an issue setting up email encryption in Microsoft Outlook 2019 using an S/MIME certificate that I obtained through Certum as a CSR. Here are the steps I've taken so far:

Generated a CSR and obtained the certificate from Certum.

Attempted to import the certificate into Outlook.

However, I'm encountering a problem when trying to use the certificate in Outlook:

In Outlook, I go to the "File" tab.

Select "Options" at the bottom-left corner of the screen.

Click on "Trust Center," then on "Trust Center Settings."

Under "Email Security," I proceed to the settings.

When attempting to select the certificate for encryption, I should be able to click on "More Choices" to select the appropriate certificate. However, this option does not appear!

How it looks at my outlook:

Does anyone know how I can enable the "More Choices" option or know of an alternative way to install the certificate? I've already tried running Outlook as Administrator, but no success.

Thanks in advance for your help!

Answer 1

Hi @Robert Rudolph

What is your account type? A Microsoft 365 account?

Do other users in the organization have the same problem?

As far as I know, before you can choose a certificate using the method you mentioned, you have to add the certificate to the keychain on your computer first. Once you have set up the signing certificate on your computer, you need to configure it in Outlook. More information, see: Encrypt email messages - Microsoft Support.

For S/MIME certificates with CSR, this article may be helpful to you.

https://www.sslmarket.com/blog/how-to-get-and-start-using-an-s-mime-certificate-with-csr.

(Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.)

---

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

---