1 of 4 This document is for informational purposes only. MICROSOFT MAKES NO WARRANTIES, EXPRESS OR IMPLIED, IN THIS DOCUMENT. © 2006 Microsoft Corporation. All rights reserved. Protect an Message (IRM) Set a Message to Expire (IRM) Digitally Sign a Message (S/MIME) Encrypt Messages (S/MIME) Get a Digital ID (S/MIME) Information Rights Management (IRM) and S/MIME offer several ways to ensure that messages sent from Outlook are secure and authentic. Topics in this guide: In Outlook, click File, point to New, and then click Mail Message. To restrict permission to your message, click Permission on the Outlook toolbar. The following message appears at the top of the message window: Note To remove restricted permission, click Permission again. Protect an Message (IRM) Create messages with restricted permission to help prevent sensitive messages from being forwarded, printed, or copied. 1 2 In Outlook, click File, point to New, and then click Mail Message. On the Outlook toolbar, click the arrow next to Options, and on the menu that appears, click Options. In the Message Options dialog box, under Delivery options, select the Expires after check box, choose a date and time, and then click Close Set a Message to Expire (IRM) With IRM, you can set messages to expire after a specific date and time.

2 of 4 This document is for informational purposes only. MICROSOFT MAKES NO WARRANTIES, EXPRESS OR IMPLIED, IN THIS DOCUMENT. © 2006 Microsoft Corporation. All rights reserved. Note If you use Microsoft Word as your editor, there is a quick way to digitally sign a message. With the new message open, on the default toolbar, click the button. This button will not appear until you have followed the steps above and have a digital signature for the message. See the Get a Digital ID topic at the end of this guide for more information. With the message open, click Options, and then select Options. When the message expires, the recipient can still see the message header in Microsoft Outlook ® folders with a line through the header text, but they cannot open or take any other actions on the message. Digitally sign a message to apply an authorized certificate that proves to the recipient the message is from you, and that the message has not been altered. Digitally sign messages individually, or sign all messages at once. 1 2 Select the Add digital signature to this message check box. If available, you may select one of the following options: 3 To enable recipients who don't have S/MIME security to read the message, select the Send this message as clear text signed check box. By default, this check box is selected. To verify that the digital signature is validated by the recipient and that the message was received unaltered, as well as to be notified of who opened the message and when it was opened, select the Request S/MIME receipt for this message check box. When you send a message with an S/MIME return receipt request, this verification information is returned as a message sent to your Inbox. 4 5 Click Security Settings. To change additional settings, such as choosing a specific certificate to use, click Change Settings, make the changes, and then click OK. When you are done, click OK, and then click Close. Digitally Sign a Message (S/MIME) Note To obtain a signature certificate, you must enroll in S/MIME, which places the certificate on your smart card. To digitally sign a message, you will be prompted to insert your smart card and enter your PIN. See the Get a Digital ID topic at the end of this guide for more information.

3 of 4 This document is for informational purposes only. MICROSOFT MAKES NO WARRANTIES, EXPRESS OR IMPLIED, IN THIS DOCUMENT. © 2006 Microsoft Corporation. All rights reserved. Select the Add digital signature to outgoing messages check box. 3 2 To enable recipients who don't have S/MIME security to read the message, select the Send clear text signed message when sending signed messages check box. This check box is selected by default. To verify that the digital signature is validated by the recipients and that the message was received unaltered, as well as to be notified of who opened the message and when it was opened, select the Request S/MIME receipt for all S/MIME signed messages check box. When you send a message with an S/MIME return receipt request, this verification information is returned as a message sent to your Inbox. 1 2 Encrypt Messages (S/MIME) Keep messages private with encryption. Only a recipient with a private key that matches the public key you used to encrypt the message can decipher the message. Encrypt messages individually, or encrypt all messages you send. To digitally sign all messages you send: 1 In Outlook, Click Tools, select Options, and then click the Security tab. If available, you may select one of the following options: In the message, click Options. Click Security Settings. To change additional settings, such as choosing a different certificate to use, click Settings, make the changes, and then click OK. Note To obtain an encryption certificate, you must first enroll in S/MIME, which places the certificate on your smart card. To encrypt a message, you will be prompted to insert your smart card and enter your PIN. For more information, see the Get a Digital ID topic at the end of this guide. When you are done, click OK Select the Encrypt message contents and attachments check box. To change additional settings, such as choosing a specific certificate to use, click Change Settings, make the changes, and then click OK.

4 of 4 This document is for informational purposes only. MICROSOFT MAKES NO WARRANTIES, EXPRESS OR IMPLIED, IN THIS DOCUMENT. © 2006 Microsoft Corporation. All rights reserved. Note If you use Microsoft Word as your editor, there is a quick way to encrypt a message. With the new message open, on the default toolbar, click the button. This button will not appear until after the first time you’ve followed the steps above and have a digital signature for the message. For more information, see the Get a Digital ID topic at the end of this guide. To encrypt all messages you send: In Outlook, on the Tools menu, click Options. 1 2 Notes To send encrypted messages over the Internet, you need to swap certificates (.cer files) with the recipient. You can do this by sending a digitally signed message. The recipient adds your name to Contacts and in doing so also adds your certificate If both you and the recipient are enrolled in S/MIME, it is not necessary to swap certificates. Click OK, and then click Close. 5 On the Security tab, select the Encrypt contents and attachments for outgoing messages check box. Get a Digital ID (S/MIME) To encrypt or digitally sign messages, you must get a certificate from a certifying authority by enrolling in S/MIME and obtaining a Digital ID. Go to Add URL here and add yourself to the appropriate distribution group.