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Exchange Server 2010 : Understanding Public Key Infrastructure (part 2) - Manual Encrypted Communications Using Outlook

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3/26/2011 9:39:55 PM

Manual Encrypted Communications Using Outlook

Specific to this article, encryption is used for email communications to allow users to send and receive secured communications. An encryption system is built in to Exchange Server that allows users within an Exchange Server environment to send email messages to other users within their Exchange Server environment in an encrypted manner. The problem with the default encryption in Exchange Server is that it does not provide encryption outside of the company’s Exchange Server environment. So, most organizations do not use the built-in email encryption in Exchange Server, but rather use a more standard method of encrypted communications built on the PKI standard.

You have several methods of providing encrypted communications between users within and external to a Microsoft Exchange Server and Outlook email system. Users can each get a certificate from an organization such as VeriSign and perform encrypted communications. Or, an organization can purchase an enterprise license of Pretty Good Privacy (PGP) that provides encryption between users and organizations also using PGP email security. In this example, the use of individual VeriSign certificates is noted.

In this case, a user who wants to encrypt messages between himself and someone else needs to get an individual email certificate and install that certificate in his Microsoft Outlook email client software. In this example using VeriSign, the user would go to www.verisign.com/authentication/individual-authentication/digital-id/index.html and for approximately $20 per year, both individuals wanting to conduct secured communications can purchase a certificate. The individuals share the public portion of their certificates with the other individuals and they can now send encrypted messages back and forth.

To acquire a certificate, do the following:

1.
Go to a certificate provider such as VeriSign, and sign up and purchase a digital ID: www.verisign.com/authentication/individual-authentication/digital-id/index.html.

2.
Follow the instructions to download and install the certificate in your Outlook client.

3.
Have the individual you want to communicate with do the same.

This process of purchasing, downloading, and installing a certificate needs to be done only once per year.

Note

If you use multiple computers, you need to install the certificate on each machine on which you run the Outlook client to be able to send and receive encrypted email messages.


After you have downloaded and installed the certificate on your computer, you need to configure Outlook to support the certificate. To do so, do the following:

1.
Launch Outlook.

2.
For Outlook 2003 and earlier, choose Tools, Options, and then click the Security tab. For Outlook 2007, choose Tools, Trust Center, and then click Email Security.

3.
Click the Settings button.

4.
In the Security Settings Name text box, type Email Encryption. Using the Cryptographic Format list arrow, choose S/MIME. Check the Default Security Setting for This Cryptographic Message Format and the Default Security Settings for all Cryptographic Messages check boxes.

5.
Next to the Signing Certificate box, click Choose.

6.
From the Select Certificate page, select the certificate that was previously installed and click OK.

7.
Using the Hash Algorithm list arrow, choose SHA1. Using the Encryption Algorithm list arrow, choose 3DES.

8.
Check the Send These Certificates with Signed Messages check box.

9.
The settings should look similar to the ones shown in Figure 1. Click OK to apply these settings, and then click OK again.

Figure 1. Configuring Microsoft Outlook to support encryption certificates.


The Outlook client is now ready to send signed and encrypted emails. Individual users, depending on how computer savvy they are, might have difficulties signing up, downloading, and installing the certificate, and then configuring Outlook to send emails. In addition, because the certificates are individual based, each individual user has to do this process themselves every year and for every system on which they conduct email communications.

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