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Use these instructions to enable Outlook to use client certificates for digitally signing and/or encrypting email Enable digital signing and encryption Use your client certificate with Outlook for macOS

If you do not have certificates for everyone to whom the message is addressed, you will be prompted to send the message unencrypted.

In the lower right of the message header, click the open lock icon to lock it when the icon is locked, your email message will be encrypted. If you have the public certificate for the recipient(s) to whom the message is addressed, you will be able to encrypt the email message. Because digital signatures are sent as attachments, which some mailing lists do not accept, you may not want to digitally sign messages sent to mailing lists.