Secure Messaging Challenge Technical Demonstration

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Ethan Gilbert
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1 Secure Messaging Challenge Technical Demonstration The Open Group EMA Forum

2 Boeing s Messaging Needs Provide access to strongly encrypted outside the enterprise Reduce complexity of deploying secure Present a single solution which can span the enterprise Provide broadly acceptable solution to customers, partners, suppliers

secure e-mail Present a single solution which can span the

3 Technical Requirements Use X.509 v3 CA Services Self-signed or purchased commercial certificates RSA algorithm with minimum 1024-bit key length Provide standards-based directory services accessible via the public Internet Certificate stored in standard usercertificate attribute Provide S/MIME compliant messaging client capable of requesting certificates from the directory Provide S/MIME compliant system Follow current standards regarding S/MIME, X.509 v3 and LDAP v3 COTS or open source products only

standards-based directory services accessible via the public Internet Certificate stored in standard usercertificate attribute

4 Scope Organization 2 Intranet Challenge Boundary Organization 1 Intranet Request to LDAP proxy with recipient's address External LDAP Proxy Internal LDAP Proxy LDAP Server with User Entries & Certificates LDAP Server or Proxy x509 v3 Public Key Desktop PC Desktop PC Network Firewall Public Network Network Firewall S/MIME Compliant Server Normal Message Route Normal Message Route Messaging Backbone Services Exchange Server

LDAP Server or Proxy x509 v3 Public Key Desktop PC Desktop PC Network Firewall Public Network Network

5 Deliverables Toolkit PKI Overview Certificate practices, guidelines and recommendations Lessons Learned Example architectures Comprehensive testing results Peer reviewed report of findings and recommendations

Learned Example architectures Comprehensive testing

6 EMA Challenge Timeline Recruiting Scope Initial Architecture Testing and Validation Reporting and Demonstration Deployment Jul Sep Oct Nov Dec Jan Feb Mar Apr

7 Lynx Systems Lotus Notes and Test Solution A: Server: Lotus Notes Client: Lotus Notes LDAP: Lotus Notes Microsoft Exchange Test Solution B: Server: Microsoft Exchange 2000 Client: Microsoft Outlook 2000 SR1 and Security Patch LDAP: Linux with Open LDAP PKI Self-Signed Signed Root Certificate Authority on Microsoft Windows 2000 CA Server, Standalone

8 Server Lotus Notes DMZ A Notebook Mobile User Intranet Firewall Notebook Work Station Firewall Internet MS Windows 2000 PKI Linux Server + Open LDAP DMZ B Server Exchange

9 Boeing Demo Environment Messaging Environment Server: Microsoft Exchange 2000, and Key Management Server Client: Outlook 2000 SP2 Directory Environment Windows 2000 Active Directory PKI Environment Boeing Self-signed Root Microsoft Windows 2000 Standalone Subordinate CA Server LDAP presence Internal and External LDAP Proxy Servers Maxware Virtual Directory

Directory PKI Environment Boeing Self-signed Root Microsoft Windows 2000 Standalone

10 Boeing Demo Environment Boeing Test Self-Sign Root Certificate Authority Internet Microsoft Windows 2000 Test Standalone Subordinate Certificate Authority External LDAP Proxy Maxware Virtual Directory Internal LDAP Proxy Maxware Virtual Directory Microsoft Windows 2000 Active Directory Microsoft Exchange 2000 Workstation With Microsoft Outlook 2000 SP2 Firewall Microsoft Exchange 2000 Key Management Server

Internal LDAP Proxy Maxware Virtual Directory Microsoft Windows 2000 Active Directory Microsoft

11 SMTP/Vendor Certificate Architecture Messaging Environment Server: Sendmail and POP3 daemon on Linux Client: Outlook 2000 SP2 Directory Environment Directory.verisign verisign.com Directory server for Verisign issued certificates PKI Environment Purchased Verisign Class 1 X.509 V.3 certificates

Environment Directory.verisign verisign.

12 SMTP/Vendor Certificate Architecture Purchased user certificates from directory.verisign.com Internet Workstation with Microsoft Outlook 2000 SP2 Linux with Sendmail 8.11 & POP3 daemon

13 Demonstration Scenario 1 Boeing Exchange to Lynx Exchange Directory lookup Send/Receive encrypted message Scenario 2 Lynx Notes to Smtptestbed.com Directory lookup Send/Receive encrypted message Scenario 3 Smtptestbed.com to Boeing Exchange Directory lookup Send/Receive encrypted message Scenario 4 Lynx Exchange to Lynx Notes Directory lookup Send/Receive encrypted message

com Directory lookup Send/Receive encrypted message Scenario 3 Smtptestbed.

14 Lynx Test Environment Demonstration Environment Notebook Mobile User Intranet Server Lotus Notes DMZ A Notebook Firewall Boeing Test Environment MS Windows 2000 PKI Linux Server + Open LDAP DMZ B Server Exchange Internet Boeing Test Self-Sign Root Certificate Authority Microsoft Windows 2000 Test Standalone Subordinate Certificate Authority SMTPTESTBED.COM Test Environment External LDAP Proxy Maxware Virtual Directory Internal LDAP Proxy Maxware Virtual Directory Firewall Microsoft Windows 2000 Active Directory Microsoft Exchange 2000 Workstation With Microsoft Outlook 2000 SP2 Workstation with Microsoft Outlook 2000 SP2 Linux with Sendmail 8.11 & POP3 Daemon Purchased user certificates can be found at directory.verisign.com Microsoft Exchange 2000 Key Management Server

COM Test Environment External LDAP Proxy Maxware Virtual Directory Internal LDAP Proxy Maxware Virtual Directory Firewall Microsoft Windows 2000 Active Directory Microsoft Exchange 2000 Workstation

15 Scenario 1 Boeing to Lynx Exchange Directory Lookup

16 Scenario 1 Boeing to Lynx Exchange Read Encrypted Message

17 Scenario 2 Lynx Notes to Smtptestbed.com Directory Lookup

18 Scenario 2 Lynx Notes to Smtptestbed.com Read Encrypted Message

19 Scenario 3 Smtptestbed.com to Boeing Directory Lookup

20 Scenario 3 Smtptestbed.com to Boeing Recipient Read Encrypted Message

21 Scenario 4 Lynx Exchange to Notes Encrypted Message

22 Scenario 4 Lynx Microsoft Exchange to Lotus Notes Encrypted Mail

Exostar LDAP Proxy / SecureEmail Setup Guide. This document provides information on the following topics:

Exostar LDAP Proxy / SecureEmail Setup Guide. This document provides information on the following topics: This document provides information on the following topics: Email Encryption set-up Outlook 2003 Email Encryption set-up Outlook 2007 Email Encryption set-up Outlook 2010 Email Encryption set-up Outlook