Encrypting email with Outlook / Outlook Express:

Potential Danger of Email Decryption

Extreme care must be taken when the technology is used to encrypt email messages. Encrypted messages can only be decrypted by the required private key. Because of the very nature of the technology, it might be impossible to recover an encrypted message when the required private key is lost. If in any case the key pair does not match, the encrypted message could never be recovered.

As there are possibilities that an encrypted email can never be decrypted due to loss of the smartcard, personel turnover, etc., the encryption capability of the Personal (Smartcard) e-Cert has been disabled. In any case there is need to send/receive encrypted email, you will need to use recipent's Personal e-Cert. Please be reminded that recipents of encrypted email are advised to keep a backup copy of their Personal e-Cert by exporting it to a file.

Encrypting email with Outlook

To encrypt a message, you need to have a copy of the intended recipient's digital certificate. When you receive a signed message, you can store the sender's digital certificate in your address book. 

If you don't have someone's digital certificate, the best and the simplest way is to ask the intended recipient to send you a signed message so that your email client can encrypt the message according to recipient's cipher (cryptographic algorithm) preferences. For more information about storing and maintaining digital certificates in your address book, see Managing Contacts' Digital Certificates.

The encrypted icon indicates that a message has been encrypted. When you encrypt a message, this icon is displayed in the lower right corner of the address pane with Outlook Express. When you receive an encrypted message, Outlook Express / Outlook automatically decrypts the message and displays the encrypted icon when the message is viewed.

You can encrypt individual messages or configure your e-mail security options to automatically encrypt all e-mail messages to recipients whose digital certificates are stored in your address book.


Encrypting Individual Messages with Outlook

To encrypt an outgoing message:
  1. Compose your message as usual.
  2. Click on the Options... button in the message window.
  3. Enable the Encrypt message contents and attachments checkbox.
  4. Close the Message Options window.
  5. Click on the Send button to send your message.

Automatically Encrypting Outgoing Messages with Outlook

To configure your e-mail preferences to automatically encrypt outgoing messages to recipients whose digital certificates are stored in your address book:
  1. Open Microsoft Outlook.
  2. Select Options from the Tools menu.
  3. Click on the Security tab.
  4. Enable the Encrypt contents and attachments for outgoing messages checkbox.


Encrypting Individual Messages with Outlook Express

To encrypt an outgoing message:

  1. Compose your message as usual.
  2. When you finished, click on the Encrypt message button. The encrypted icon is displayed in the right corner of the address pane indicating that the message is encrypted.

  3. Click on the Send button to send your message.

Automatically Encrypting Outgoing Messages  with Outlook Express

To configure your e-mail preferences to automatically encrypt outgoing messages to recipients whose digital certificates are stored in your address book:
  1. Open Outlook Express.
  2. Select Options from the Tools menu.
  3. Click on the Security tab.
  4. Enable the Encrypt contents and attachments for all outgoing messages checkbox.