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Scenario
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Adventure Works implements Exchange Server 2003 in a single domain forest named adventureworks.com. The Exchange Server, ADVEXCH01, provides e-mail services to all employees of Adventure Works and is also used to send and receive e-mail over the Internet. All client computers use Outlook 2003 to connect to the mail server. All servers on the network are running Windows Server 2003, Enterprise Edi tion, and the client computers are running Windows XP. The latest service packs are installed and security updates are applied to all client computers on a weekly basis. Recently, the IT, human resources, and legal departments drafted security pol icies for the Adventure Works network. The following security policies are related to e-mail:
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Any e-mail messages containing proposed or confirmed flight itineraries to cus tomers must be signed to provide confidence to the customers that the contents are valid and did originate from the Adventure Works travel consultant. Any e-mail messages containing customer confidential information such as passport numbers, credit card numbers, and bank account information must be encrypted. In addition, any e-mail messages containing classified data must be encrypted when sent to employees. The private keys associated with encryption certificates must be archived at the issuing CA to allow recovery of the private key in the event of computer fail ure, computer rebuild, profile deletion, or corruption of the private key. All key recovery must require the participation of at least two employees to prevent unauthorized access to a user s encryption key. The private keys associated with signing certificates must never be archived in order to ensure that two users do not have access to the same signing certificate. E-mail signing and encryption private keys must be protected by a password. The password must be typed each and every time the private key is accessed.
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In addition to enforcing the security policies defined for Adventure Works, the secure e-mail project must meet the following design requirements:
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Several of the agents participate in a job-sharing program. When an agent comes into the office, there is no guarantee that he or she will sit at the same computer, so e-mail certificates must be portable. Some of the agents have laptop computers and connect to the mail server, ADVEXCH01, from remote locations. Secure access to their e-mail must be pro vided, as well as the ability to use S/MIME for signing and encrypting e-mail.
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Part III: Deploying Application-Specific Solutions
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Case Study Questions
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1. Based on the security policies related to e-mail usage, how many e-mail certif icates must be distributed to each user 2. What certificate(s) must be published to Active Directory to enable the sending of encrypted e-mail between employees of Adventure Works 3. Will the current CA infrastructure allow the e-mail signing and e-mail encryp tion certificates to be recognized by the customers of Adventure Works 4. What method would you use to deploy the e-mail certificate(s) to the Adven ture Works users What certificate template settings are required to allow this method of enrollment 5. One of the travel agents is able to open his encrypted e-mail at only one of the available agent computers. When he attempts to open his encrypted e-mail at the other computers, the attempt fails. What can you do to ensure that the travel agent can open the encrypted e-mail at any of the travel agent computers 6. How do you propose to enforce the security policy that two or more people must be involved in the recovery 7. How do you enforce that users must provide a password to access the private keys associated with the e-mail signing and e-mail encryption certificates 8. What must a travel agent do to allow a customer to send an encrypted e-mail message 9. What solution can be used to allow remote travel agents to securely access their e-mail and use S/MIME to protect the e-mail messages without enabling an additional e-mail client 10. One of the travel agents has forgotten the password used to protect the e-mail encryption certificate and can no longer read encrypted e-mail. What must you do to allow the travel agent to access the encrypted e-mail 11. When performing the proof of concept test of your e-mail solution, you are told that customers are complaining that their e-mail applications are reporting that the digital signatures are failing. You look at the certificate and find the fol lowing URLs in the CDP extension:
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LDAP:///CN=Adventure Works Issuing CA,CN=ADVCA01,CN=CDP,CN= Public Key Services,CN=Services,CN=Configuration,DC=travelworks,DC=com http://advca01/certenroll/Adventure%%20Works%%20%%20Issuing %%20CA.crl
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