CMSY 262 – ENCRYPTION AND VPN TECHNOLOGY

1.    Cryptographic Overview

1.1.        History of Cryptography
1.2.        Modern Cryptographic Influences
1.3.        Symmetric
1.4.        Asymmetric
1.5.        Today’s Algorithms
1.6.        Defining Cryptographic Terms

2.    Symmetric Cryptographic Overview

2.1.        Common Algorithms
              2.1.1.   DES-ECB
              2.1.2.   DES-CBC
              2.1.3.   DES – CFB & OFB
              2.1.4.   IDEA Overview
              2.1.5.   AES Overview

3.    Asymmetric Cryptographic Overview

3.1.        Asymmetric Encryption is: two way, two key (public & private), 
              scalable
3.2.        Common Algorithms
              3.2.1.   RSA – encryption & digital signatures
              3.2.2.   DSA – government standard – digital signatures only
3.3.        Hashing
              3.3.1.   SHA -1
              3.3.2.   MD-5

4.    Applied Cryptography

4.1.        Cryptographic Uses
              4.1.1.   Authentication
              4.1.2.   Confidentiality
              4.1.3.   Integrity
              4.1.4.   Non-Repudiation
4.2.        Symmetric vs. Asymmetric Use
4.3.        Digital Signatures
4.4.        Key Management
              4.4.1.   Key Lifecycle
              4.4.2.   Determination of risk to key
              4.4.3.   Key Length Consideration
              4.4.4.   Data Considerations – Repudiation, financial, and 
                          regulatory risk
              4.4.5.   Threats – Internal, external, third parties
              4.4.6.   Management Costs
                          4.4.6.1.   Physical Infrastructure
                          4.4.6.2.   Identification & authentication
                          4.4.6.3.   Changeover
             4.4.7.   Protection of Keys
             4.4.8.   Issuance of Keys
             4.4.9.   Revocation of Keys

5.    PKI

5.1.        Multiple types of PKI
              5.1.1.   Web of Trust
              5.1.2.   Hierarchal
              5.1.3.   Mesh
              5.1.4.   Trust
5.2.        Digital Certificates
              5.2.1.   Identity - verify
              5.2.2.   Expiration date
              5.2.3.   Public Key
              5.2.4.   Attacking Digital Certificates
5.3.        Return on Investment
              5.3.1.   SSL
              5.3.2.   VPN
              5.3.3.   EFS
              5.3.4.   S/MIME
5.4.        X.509 Public Key Infrastructure

6.    PKI Problems

6.1.        Confidentiality Regulations – require transmission & storage 
              encryption
               6.1.1.   Gramm-Leach Bliley
               6.1.2.   HIPPA – Healthcare
6.2.        Authorization Regulations – require indications of consent
              6.2.1.   E-sign Act
6.3.        Common PKI Problems
              6.3.1.   Significant Implementation Costs
              6.3.2.   Insufficient thought to operational process
              6.3.3.   Insufficient time developing ROI
              6.3.4.   Key recovery is afterthought

7.    VPN Overview

7.1.        VPN Definition
7.2.        VPN History
              7.2.1.   Secure Data Network Systems  (SDNS)
              7.2.2.   Point to Point Tunneling Protocol (PPTP)
              7.2.3.   Layer two Tunneling Protocol (L2TP)
              7.2.4.   Internet Protocol Security (IPSec)
              7.2.5.   Secure Sockets Layer (SSL)
7.3.        VPN Scenarios

8.    VPN Protocols

8.1.        PPTP
8.2.        L2TP
8.3.        IPSec
              8.3.1.   Enhanced Security
              8.3.2.   Key Management
                          8.3.2.1.   Manual Distribution
                          8.3.2.2.   Automated Distribution
              8.3.3.   User Authentication & Key Exchange using IKE
              8.3.4.   Bulk Data Confidentiality & Integrity for Message/File 
                          Transport
              8.3.5.   Implementation Incompatibilities and Complications
8.4.        SSL
              8.4.1.   History of SSL
              8.4.2.   SSL Session in Detail
              8.4.3.   TLS Variations
              8.4.4.   Comparing TLS, SSL, v3, and SSL v2

9.    VPN Tunnel Creation

9.1.        Create a Windows VPN Tunnel
9.2.        Connect to Web Server via Tunnel
9.3.        Sniff Network Traffic to evaluate Encryption
9.4.        Create a SSL tunnel
9.5.        Sniff Traffic to Evaluate Encryption

10.  Specialty Situations

10.1.      Confidentiality Using Public Keys
10.2.      SSL VPN’s
10.3.      SSH
10.4.      Citrix and Remote Desktop Connection
10.5.      VPN Concentrators
10.6.      Wireless VPS’s

11.  VPN Processes

11.1.      Business Processes
11.2.      Design
              11.2.1.   Document Requirements
              11.2.2.   Identify Stakeholders
              11.2.3.   Obtain Funding
              11.2.4.   Product Selection
              11.2.5.   Identify Risks
11.3.      Implementation
              11.3.1.   Create Project Plan
              11.3.2.   Build Test Cases
              11.3.3.    Solicit User Feedback
              11.3.4.    Create ‘Go / No Go’ decision
11.4.      Maintenance
              11.4.1.   User Support
              11.4.2.    Network Support
              11.4.3.    Monitoring
11.5.      User Authentication
              11.5.1.   Internal  Authentication
              11.5.2.   External Authentication
              11.5.3.   Dial-up Authentication
11.6.      Proper Administration
              11.6.1.   Integration with Change Management
              11.6.2.   Periodic Risk Assessments
              11.6.3.   Separation of Duties
11.7.      Best Practices

12.  Freenet

12.1.      Freenet’s Goal
12.2.      Freenet Concepts
              12.2.1.   Files are the only element – supports file sharing
              12.2.2.   Each file has unique identifier
              12.2.3.   Authors can update content via key pairs
              12.2.4.   Each node is only aware of neighbors
              12.2.5.   Each node contributes storage
              12.2.6.   Each files resides somewhere else