Digitally sign a single message
- In the message, on the Options tab, in the Permission group, click Sign Message.
- If you don’t see the Sign Message button, do the following:
- In the message, click Options.
- In the More Options group, click the dialog box launcher in the lower-right corner.
- Click Security Settings, and then select the Add digital signature to this message check box.
- Click OK, and then click Close.
- If you don’t see the Sign Message button, you might not have a digital ID configured to digitally sign messages, and you need to do the following to install a digital signature.
- On the File menu, click Options > Trust Center.
- Under Microsoft Outlook Trust Center, click Trust Center Settings > Email Security
- Click Import/Export to import a digital ID from a file on your computer, or click Get digital IDs to find a list of services that issue digital IDs for your use.
- If you don’t see the Sign Message button, do the following:
- Compose your message, and then send it.
Digitally sign all messages
- On the File tab, click Options >Trust Center.
- Under Microsoft Outlook Trust Center, click Trust Center Settings.
- On the Email Security tab, under Encrypted Mail, select the Add digital signature to outgoing messages check box.
- If available, you can select one of the following options:
- If you want recipients who don’t have S/MIME security to be able to read the message, select the Send clear text signed message when sending signed messages check box. By default, this check box is selected.
- To verify that your digitally signed message was received unaltered by the intended recipients, select the Request S/MIME receipt for all S/MIME signed messages check box. You can request notification telling you who opened the message and when it was opened, When you send a message that uses an S/MIME return receipt request, this verification information is returned as a message sent to your Inbox.
- To change additional settings, such as choosing between multiple certificates to use, click Settings.
- Click OK on each open dialog box.
Ref: Secure messages by using a digital signature – Microsoft Support