LinuxCBT OpenPGP Edition d3x

Focus: Pretty Good Privacy (PGP) Security
Duration: 11 Hours

Course Objective
OpenPGP Security - Module IX

Introduction - Topology - Features
Discuss course outline
Explore system configuration
Identify key systems to be used
Explore network topology
Enumerate and discuss key OpenPGP features

Explore GPG Configuration
Identify installed GPG packages in various Linux distros
Discuss the key contents of those packages
Explore configuration hierarchy
Discuss security as it pertains to private key management
Explain the purpose of public and private keys
Discuss symmetric and asymmetric encryption provided by OpenPGP-compliant Apps

Generate | Import | Export OpenPGP Usage Keys
Discuss features and benefits
Obtain shell access on remote systems
Generate usage (private|public) keys
Identify the generated keys
Discuss how usage keys are used
Generate usage keys on remote systems
Export OpenPGP public key chain on various systems
Import OpenPGP public keys on various systems
Evaluate the results of exchanging public keys

Digital Signatures
Discuss features and benefits as they pertain to data integrity
Identify default digital signatures on multiple hosts
Explain the differences between signing and encrypting correspondence
Sign and export data to remote systems - Inline
Create detached OpenPGP signatures for data
Confirm the signed data on the remote systems
Recap non-repudiation benefits provided by digitally signing correspondence

Encryption | Decryption | Sign & Encrypt Content
Discuss features and benefits
Generate files for usage
Encrypt content using symmetric (shared-key) algorithm
Decrypt content using the shared-key, based on the symmetric algorithm
Evaluate results on multiple machines
Explain caveats associated with symmetric encryption
Encrypt content to a given recipient, using their public key - asymmetric encryption
Decrypt content on various hosts
Attempt to decrypt content without the corresponding private key
Evaluate results
Encrypt using ASCII-armoured and binary (OpenPGP-compliant) formats
Decrypt both ASCII-armoured and binary formats
Recap encryption decryption processes
Discuss the requirements of signing and encrypting content
Sign and encrypt content to various recipients
Confirm signed and encrypted content
Attempt to confirm and decrypt content as the unintended recipient
Evaluate results

OpenPGP Key Management | Web of Trust | Internet Key Distribution
Discuss features and benefits
Explore GPG key management facility
Update properties of public/private key pairs
Add sub-keys to public/private key pairs
Sign remote users' public keys
Evaluate results
Discuss the web of trust functionality
Create a web of trust with various hosts
Evaluate trust confirmation
Discuss the features of OpenPGP Internet key distribution servers
Generate and upload public keys to an Internet key server
Download the uploaded public keys to the public keyrings of various hosts
Evaluate results

Perl Scripting with GPG
Discuss features and benefits
Create a Perl script to backup key directories and files
Ensure that the script GPG-protects the content post-backup
Include error-handling to ensure that each step of the script is routed appropriately
Configure the script to transfer the encrypted content to a remote host ust 'scp'
Evaluate results

OpenPGP (GPG | PGP Desktop) on Win32
Discuss features and benefits
Download and install GPG for Win32
Generate usage keys
Exchange public keys with a user on a Linux system
Sign and encrypt content to and from the Win32 user
Confirm results
Download and install GPG4WIN (GUI-based GPG for Win32)
Explore features
Sign and encrypt content to and from the Win32 user
Confirm results
Integrate GPG4WIN with MS Outlook
Sign and encrypt e-mail messages
Confirm and decrypt e-mail messages
Install PGP Desktop for Win32
Explore features and interface
Generate usage keys
Exchange public keys with Linux user
Sign and encrypt content to and from the Win32 user using PGP Desktop
Evaluate results
Draw parallels between Win32 based OpenPGP tools and GPG for Linux | Unix
Recap OpenPGP functionality included in /GPG|GPG4WIN|PGP Desktop/