Installing and using your certificate in Microsoft Outlook 98 and 2000

• Installing your certificate
• Digitally signing your e-mail messages
• Encrypting / scrambling your e-mail messages
• Customizing your Microsoft Outlook to have the Signing and Encryption buttons appear on your toolbar
• Managing correspondents’ digital certificates
• Saving a digital certificate from a signed message
• Importing a downloaded digital certificate
• Removing a digital certificate

Installing your certificate

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

• Choose "Tools" in the Outlook menu bar
• Choose "Options"
• Choose the "Security" tab

To define your security settings and to specify which certificate you wish to use you need to define your default security settings. To do so you need to click the "Settings..." button. You will then see the following screen:

You can create different security settings and give these separate names. You can define the following settings :

• Secure Message Format (type of e-mail)
• Digital Signature Settings
• Encryption Settings
• Security Setting Preferences (setting defaults)

The ‘Digital Signature’ settings allow you too choose a certificate which will be used to sign your emails. You need to click the ‘Choose…’ button to receive the following screen :

This screen allows you to define which certificate you wish the use for signing purposes in the settings you are about to define.
You can view the certificate by clicking on the ‘View Certificate…’ button. You will then receive a screen which gives an overview of the certificate. This will be similar to the following picture :

The ‘Digital Signature’ settings section also allows you to define which type of hashing algorithm you want to use for the creation of your signatures (SHA-1, MD5)
The ‘Encryption’ settings allow you too choose a certificate which will be used to sign your emails. You need to click the ‘Choose…’ button to receive the same screen as presented previously.

Digitally signing your e-mail messages

The first step to 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 package, he can still read your message. In that case, your digital signature shows up as an attachment. The signed icon shows that the received message was signed.

The untrusted signature icon shows that the received message was signed by a certificate which was issued by a CA which you do not trust yet (because you have not installed its root certificate). This icon looks as follows :

You can sign your messages each time you want to sign or you can configure your security settings (as described previously) to sign using a specific certificate.

Encrypting / scrambling your e-mail messages

The second step to secure 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. Encrypt with Outlook 98 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, you can save the certificate of the sender in your Contacts List. You need to create an entry in the Contacts List if you want to send encrypted email to that person. You must also import his digital certificate into the Contacts List.
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.

When you receive an e-mail, the encrypted icon indicates that the message has been encrypted. This icon appears in the lower right corner (blue padlock) of the address pane. The encryption process is done automatically.
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 enrypted every time the digital certificate resides in your address book.
When you receive an encrypted message the encrypt icon appears on the email window:

Customizing your Microsoft Outlook 98 or 2000 to have the Signing button and the Encryption button appear on your toolbar

1. From your toolbar click on New message button

2. Click on Customize From the Next dialog box

3. Select the Commands Tab

4. In the Categories list select Standard

5. To have the Encrypt Message button appear on your toolbar, select it and move it to the Toolbar holding down the mouse as shown below :

By following the same procedure For the Digitally Sign Message you will end with the following screen

Click on Close to finish this procedure

Managing correspondents’ digital certificates.

To send someone an encrypted message, you need a copy of their digital certificates in your Contacts List. Outlook 98/2000 makes it easy to view, add and remove certificates.

Saving a digital certificate from a signed message.

When you receive a signed encrypted message, you can save the digital certificate of that person in your Contacts List. You first need to click on the signed icon represented as :


This will give you the following screen :

This screen gives you more information about the certificate which was used for signing the email in se. If you want to view the certificate and all its detail, you need to click the ‘View Certificate…’ button. This will give you a screen which is similar to :

Clicking on the ‘Details’ tab will give you the following screen :

Clicking the ‘Copy to File…’ allows you to export the specific certificate to file. You can now import this certificate into your Contacts List (as described further).

Saving a digital certificate from an signed and encrypted message.

When you receive a signed encrypted message, you can save the digital certificate of that person in your Contacts List. You first need to click on the signed icon represented as :

This will give you the following screen :

This screen indicates which hashing algorithm was used for the creation of the digital signature and also allows you to view the certificate in se.
Clicking on the ‘Encryption Certificate…’ button will give you the ‘View Certificate’ window as presented previously. This window allows you to copy the certificate to file through the ‘Copy to File…’ button.

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 in Outlook 98 a new address or open an existing one in your Contacts List
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.

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"

Note: When you remove someone’s digital certificate you will no longer be able to send encrypted messages to that person.