Pretty Good Privacy (PGP) Security

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
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• 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
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• 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
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• 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
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• 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
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• 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
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• 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
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• 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/
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Sums

• Various Tools
• Remote Confirmations
• File Metadata
• File Fragments
• Compress Content
• Archive Content
• DIR Hierarchy
• Password Sums
• Shared Secret
• Restrict History
• Downloaded Content
• Encrypt Content
• Site Credentials
• Site COOKIE
• Site COOKIE - Unique

CentOS9x Stream Administration

• Initial Environment
• ls, pwd, cd, cp, mv, rm, mkdir, rmdir, whoami
• alias, cat, file, chmod, chown, history
• STD(IN|OUT), Pipes, Redirection, Command Chaining
• ps, df, top, free
• Pagers, W-Commands
• Checksums
• Awk | Sed | Grep Usage
• BASH SHELL Environment
• Compression | Archival Tools
• SSH Equivalence
• SHELL Quoting
• Propagate Environment
• Secure Clients

• Identify Standard File Types
• Standard File Permissions
• Symbolic Links
• Transfer Permissions

• Identify SWAP environment
• Provision dedicated SWAP partitions
• Add | Remove SWAP from pool as needed
• Provision File System-based SWAP
• SWAP Share
• SWAP Persistence
• Identify default storage configuration
• Provision new storage as needed
• XFS - File System
• XFS - Grow File System
• Identify LVM defaults
• Add new partitions to LVM management
• Allocate storage to LVM Volume Groups
• Create Logical Volumes (LVs) as needed
• Overlay File System and mount where applicables
• LVM - Resize
• LVM - Mixed FS
• LVM - SWAP

• Features
• Install
• Defaults
• General Usage
• Update Accounts

• Defaults
• Shared PASS Gen
• Unique PASS Gen
• Encrypted PASS Gen
• Update Accounts
• Groups

• Discuss features | limitations
• Identify default system-wide schedule
• Peruse various default Cron Jobs
• Schedule simple job and monitor recurrence
• Evaluate results

• Peruse Default CONF
• Discuss Syslog Rules
• Explore Log Rotate defaults
• Ensure rotated logs are compressed
• Extend default retention scheme
• Force Log Rotation as needed

• Explore Default environment
• Install PKGs
• Dump important metadata from packages
• Apply Updates

• Default CONF
• Add | Confirm IPs as needed

• Install
• Copy Configuration
• SELinux - Confirm
• TLS | SSL Services
• cURL Client Tests
• Virtual Hosts
• ENC Sites Only

• SFTP Only USER
• SFTP Only USER - NOLOGIN
• SFTP Only Group - Control
• NMap Intro

SysLOG with rSysLogD

• Discuss Features
• Default Environment
• Kernel Firewall LOG
• Split LOGs by Priorities
• UDP | TCP Logging
• Dual L4 Logging
• Multiple Hosts
• Basic Queueing
• Reliable Event Logging Protocol (RELP)
• RELP - Remote Only
• RELP Only
• Traditional to RELP
• SysLOG Clear-Text - Confirm
• Property Filters
• Expression Filters
• Relay Chain

Netfilter Tables

• Features
• SSHGuard
• Ruleset Basics
• Persistence
• Sample Rules
• Inbound Filtering
• Dormant Table
• Manage Tables | Chains | Rules
• Counters
• Sets
• LOG Basics
• LOG with Sets
• Closed-Port LOGs
• LOG Options
• Re-Route LOGs
• Jump Targets
• Chain Jumping
• GoTo Chains
• Meta Selectors

Debian 12x Administration

• Features
• Download
• Graphical Install
• Text Install
• Post-Install Tweaks

• Explore usage of the following useful commands
• tty | /dev/pts | w | whoami | who
• set | env | export | unset
• cat | echo | touch | rm
• pwd | ls | cd | mkdir | alias | umask
• head | tail
• dd
• find
• history
• STDIN, STDOUT, STDERR, UNIX Pipes, Redirection, Command Chaining
• ps, df, free, top, dd
• stat, which, w, who
• tar | gzip | bzip2 | xz
• ZSH Setup

• Network Tools | IP Configuration
• Examine default IP configuration
• Extend IP configuration to facilitate additional addresses
• Static IP Config
• Dual: Dynamic | Static Config
• Multiple Interfaces
• Dual Network Services
• Confirm communications

PHP One-Liners

• General Usage
• Count Lines
• Word Count
• Count Chars
• Split Lines into ARRAY
• Count Instances of Fields
• Transform Delimiters
• Anonymize LOGs
• Extract Unique SRCs
• Lines by Error Code
• LOG By Code
• Summarize Error Codes
• Pre-Seed Error Codes
• Random Strings
• Varied Passwords
• Expose Undefined Passwords
• Outdated Passwords
• Hash | Un-Hash

Cloud Storage with GlusterFS

• Discuss Features:
• Default Volume Type
• Common Volume Types
• Transport Types
• File System Support
• Storage Model

• Features
• Provision Storage
• Allocate GlusterFS Brick
• Persistence
• Generate IO
• Multiple File Systems
• Various Sizes
• Stop | Remove Volume
• Reconstitute Volume
• Server Mount
• Evaluate

OpenPGP with GPG

• Discuss Features:
• Primary Tool
• Private | Public Keys
• Public Key Cryptography Standards (PKCS)
• Encryption | Decryption
• Signing | Verification

• Features
• General Usage
• Create Content
• Encrypt
• PassPhrase Protect
• Binary | Text Encryption
• Share
• Decrypt

SSL-TLS with OpenSSL

• Discuss Features:
• Primary Tool
• Private | Public Keys
• Certificate Signing Requests (CSRs)
• Self-Signed Certificates
• Public Key Cryptography Standards (PKCS)
• Encryption | Decryption
• Random String Generation
• Message Digests
• SSL-TLS Client

• Features
• General Usage
• Retrieve Site Certificates
• Determine OCSP Configuration
• Probe supported TLS Versions
• Extract Certificate for local usage
• Retrieve Certificate with NMap
• Retrieve Certificate Chain

• Discuss
• Generate Private Keys
• Generate Correlating CSRs
• Confirm Keys | CSRs
• Self-Signed Certificates

SSH Variables

• Discuss Features
• Bare VARs
• SSH Client
• Double Quotes
• Single Quotes
• SSH Environment

SHELL Variables

• Discuss Features
• Terminal (TTY)
• CLI Arguments
• Process ID
• Backgrounded
• SHELL Local
• Environment
• Persistence
• Aliases
• Command Substitution
• Increment | Decrement
• Dynamism