For Signing algorithm, the default value of SHA-256 is appropriate for most. If you try to send a digitally signed e-mail using your personal certificate before the certificate authority is trusted, then Outlook displays the message “Microsoft Outlook cannot sign or encrypt this message because your certificate is not valid. In the Digital signing section, select your certificate from the drop-down menu. ![]() If a certificate authority is not trusted, then any certificates issued by that certificate authority are not trusted and they are considered invalid by Outlook. Since we’re using self-signed certificates, Windows and Outlook will not automatically recognize your personal certificate authority. Part 1 – Trusting the Self-Signed Certificate Authority This guide describes the process for using self-signed S/MIME certificates with Microsoft Outlook 2019 found in the Microsoft Office Professional Plus 2019 suite running on Windows 10. This will enable you to type the text and image/s associated with your signature in the Edit signature text box. As long as the e-mail client supports S/MIME, which Outlook does support, then you can create and use your own certificates for any e-mail address including custom domains, Gmail, iCloud, or even AOL. The signature you just created will be highlighted in the Select signature to edit window. ![]() If you followed my guide to create self-signed S/MIME certificates, then you will have the necessary files to begin digitally signing and receiving encrypted e-mail.
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