Installing and using your certificate in Microsoft Outlook Express

• Installing your certificate
• Digitally signing your e-mail messages
1. Signing individual messages
2. Automatically signing every outgoing message
• Encrypting / scrambling your e-mail messages
  1. Encrypting individual messages
  2. Automatically encrypt every outgoing message
• Managing correspondents’ digital certificates
• Saving a digital certificate from a signed message
• Importing a downloaded digital certificate
• Removing a digital certificate
• Import your private key and certificate into Outlook Express' proprietary key-store

Installing your certificate

After installing your certificate in Internet Explorer, it will be available for use in Outlook Express. To use your certificate in Outlook Express, do the following:

• Choose "Tools" in the Outlook Express menu bar and then "Accounts"
• Choose "mail", and then select the connection you use for your email
• Click on "properties" and afterward on "security"
• Under "Select the signing certificate below"

Click on 'Select' and choose the certificate you want to use

Click OK

Repeat steps 3-5 for your Encryption certificate

Digitally signing your e-mail messages

The first step of securing your e-mail messages is to sign them using your digital certificate.
Your digital signature enables the recipient of your message to verify that you actually sent the message and that it was not altered along the message route.
When you sign your message, it doesn't mean that anybody can intercept or read your message. Signing a message does not affect the contents of the message in any way or protect the message from being intercepted and read by someone other than the intended recipient. To ensure that only the recipient can read a message, you must also encrypt the message.
If the recipient of your signed message uses an S/MIME-enabled e-mail client, he can still read your message. In that case, your digital signature shows up as an attachment.

The signed icon shows that the message was signed. When you sign the message, this icon appears on the lower right corner of the address pane.
Your e-mail program verifies your digital signature automatically for you.

You can sign your messages each time you want to sign or you can configure your security option in the way that your messages will be automatically signed every time.

Signing individual messages

To sign an outgoing message: click on the 'digitally sign message' icon (envelope with red label) in the message window.

On the lower right corner of the address pane appears the icon with the signature.
If you click again on 'digitally sign message', the digital signature will disappear.

Automatically signing every outgoing message

To configure the options for your e-mails:

1. Select in Outlook Express, 'Options' in the 'Tools' menu.
2. Click on 'Security'.
3. Enable 'Digitally sign all outgoing messages'

Encrypting/scrambling your e-mail messages with Outlook express

The second step to securing your e-mail messages is to encrypt them.
E-mail messages are relatively easy for other people to intercept or read.
You can avoid this by encrypting your messages so that only the recipient of the message can read it.
Encrypting with Outlook Express is as easy as signing.

To send someone an encrypted message, you need a copy of their digital certificate in your Contacts List. When you receive a signed message, Communicator automatically stores the sender's digital certificate. You can also find someone's digital certificate from an online directory so that you can send them an encrypted message without first receiving a signed message from them.

To have more information about maintaining digital certificates in your Contacts List, see "Managing correspondents' digital certificates"

The encrypted icon indicates that the message has been encrypted. When you encrypt a message, this icon appears in the lower right corner (blue padlock) of the address pane.
When you receive an encrypted message, Outlook Express will automatically decrypt your message and show the 'encrypted' icon.
You can encrypt your messages each time you want to encrypt or you can configure your security options so that your messages will be automatically encrypted every time the digital certificate resides in your Contacts List.

Encrypting individual messages

To encrypt an outgoing message, click on 'encrypt message' (envelope with a blue padlock) in the message window.
The 'encrypt' icon appears on the lower right corner of the address pane and shows that the message was encrypted.
If you click again on 'encrypt message', the encryption disappears.

Automatically encrypting every outgoing message

To configure your e-mail options so your outgoing messages will be automatically encrypted when the addressee's digital certificate resides in your Contacts List:

1. Open Outlook Express
2. Select 'Options' in the 'tools' menu
3. Choose 'security'.
4. Click 'encrypt contents and attachments for all outgoing messages'.

Managing correspondents' digital certificates.

To send someone an encrypted message, you need a copy of their digital certificates in your Contacts List. Outlook Express makes it easy to view, add and remove certificates.

Saving a digital certificate from a signed message.

When you receive a signed message, you can save the digital certificate of that person in your Contacts List.

1. Open the signed message
2. Using your right mouse button, click on the senders name (or email address) beside "From:" and select 'Add to Address Book'.

Your contacts digital certificate will be stored together with his/her details.

Importing a downloaded digital certificate

You can search for a digital certificate in an online database, download and add in the Contacts List so that you can send an encrypted message to that person.
To import a downloaded digital certificate in your Contacts List:

1. Create a new address in Outlook Express or open an existing one in your address book
2. Choose 'digital ID's'
3. Choose 'import'
4. Select the downloaded file with the digital certificate and choose 'open'

Removing a digital certificate from your Contacts List

1. Open the address of the person from whom you want to remove the digital certificate.
2. Choose 'digital IDs'
3. Select the certificate you want to remove
4. Click on 'remove'

When you remove someone's digital certificate you can no longer send encrypted messages to that person.

Import your private key and certificate into Outlook Express' proprietary key-store
(In order to password protect access when sending signed messages).

1. Start up your Outlook Express.

2. Select the menu "Tools" => "Options".

3. In the "Options" pop-up window, click the "Security" tab.

4. In the "Secure Mail" section, click the "Digital IDs..." button.

5. The "Certificate Manager" window will pop up. The "Personal" tab should be the default.

6. Click the "Import" button. Pop-up windows will appear one by one. Click the "Next" button till you are asked to "Select File to Import". Click the "Browse" button and select the certificate you want to import. Click the "Next" button.

7. You will be prompted to enter the password protecting your private key in the specified file. Also click the check-boxes of the options "Enable strong private key protection" and "Mark the private key as exportable". Then click the "Next" button.

8. Another window will pop up. Keep the default chosen selection "Automatically select the certificate store based on the type of certificate". Keep on clicking the "Next" button and finally the "Finish" button.

9. The "Private Key Container" window appears. Click the "Set Security Level" button.

10. Select the "High" option. Then click the "Next" button.

11. Input in the field "Password for" a name identifying your private key. In the fields "Password" and "Confirm", input a password to protect your private key installed in the Outlook Express key-store. (It is up to you whether you wish to choose the same password as the one protecting the Private-Key, but not recommended). Next click the "Finish" button.

12. Then in the final screen of the pop-up window "Private Key Container", input your chosen password in the previous step once again (note: this password is protecting your private key in the Outlook Express key-store, not password protecting the Private-Key).

13. Finally, the message window "The import was successful" will appear. Click the "OK" button.

When you come to using your certificate, you will be presented the following screen asking for your password (Do NOT click the check-box "Remember password" since securitywise it is better to type in the password every time than let Windows store your password in your PC.)