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Curriculum lobby
0s40 min Loop40 minโ˜… 160 XP
Syllabus

Security Protocols & Standards: Architecting Secure Communications

Cryptographic Foundations for ProtocolsSymmetric vs. Asymmetric Encryption (AES, RSA, ECC)Hash Functions (SHA-2, SHA-3) & Message Authentication Codes (HMAC)Digital Signatures & Certificates (X.509)Key Exchange Algorithms (Diffie-Hellman, ECDHE)Random Number Generation & Entropy SourcesCryptographic Protocol Threat Model (MitM, Replay, Downgrade)
TLS/SSL โ€“ Transport Layer SecuritySSL History & Deprecation (SSLv2, SSLv3, POODLE)TLS Versions (1.0, 1.1, 1.2, 1.3) โ€“ What ChangedTLS Handshake Protocol (Full vs. Session Resumption)TLS Record Protocol (Encryption, Padding, Sequencing)Cipher Suites (Key Exchange, Authentication, Encryption, Hash)X.509 Certificates (CA Hierarchy, Root vs. Intermediate, Let's Encrypt)TLS Extensions (SNI, ALPN, OCSP Stapling)TLS Attacks (Heartbleed, BEAST, CRIME, Lucky13, Renegotiation)Hardening TLS (Disabling Weak Ciphers, HSTS, HPKP)TLS Tools (testssl.sh, SSL Labs, openssl s_client)
HTTPS โ€“ HTTP Over TLSHTTP vs. HTTPS โ€“ What TLS AddsStrict Transport Security (HSTS) & Preload ListsStrict Transport Security (HSTS) & Preload ListsMixed Content (Passive vs. Active) โ€“ Risks & MitigationHTTP/2 & HTTP/3 (over QUIC) Security ImplicationsHTTPS Inspection (Break and Inspect) โ€“ Enterprise TLS InterceptionCertificate Pinning (HPKP Deprecated, Modern Alternatives)
SSH โ€“ Secure ShellSSH Architecture (Transport, Authentication, Connection Layers)SSH Versions (SSH-1 vs. SSH-2) โ€“ Why SSH-1 is DeadSSH Key Exchange (Diffie-Hellman Group Exchange, Curve25519)User Authentication Methods (Password, Public Key, Keyboard-Interactive, GSSAPI)Host Key Verification (known_hosts, TOFU, SSHFP DNS Records)SSH Tunneling (Local, Remote, Dynamic Port Forwarding)SSH Agent & Agent Forwarding (Security Risks)Hardening SSH (Disable Root Login, Key-Only, Fail2Ban, Port Knocking)SFTP vs. SCP vs. FTPS (Security Comparison)SSH Tools (OpenSSH, PuTTY, WinSCP, SSH-Audit)
IPsec โ€“ Internet Protocol SecurityIPsec Modes (Transport vs. Tunnel Mode)Security Protocols (AH โ€“ Authentication Header, ESP โ€“ Encapsulating Security Payload)Security Associations (SA) & Security Policy Database (SPD)IKE Phases (IKEv1 Main/Aggressive vs. IKEv2)Authentication Methods (PSK, Certificates, EAP)IPsec NAT Traversal (NAT-T) โ€“ Encapsulating ESP in UDPIPsec VPNs (Site-to-Site, Remote Access with StrongSwan/LibreSwan)Common Attacks (IKE Aggressive Mode PSK Cracking, Downgrade)IPsec vs. TLS vs. WireGuard (When to Use Which)
DNSSEC โ€“ DNS Security ExtensionsDNS Vulnerabilities (Cache Poisoning, Kaminsky Attack, Spoofing)DNSSEC Fundamentals (RRSIG, DNSKEY, DS, NSEC/NSEC3)Chain of Trust (Root $ ightarrow$ TLD $ ightarrow$ Authoritative Zone)DNSSEC Validation (AD Bit, CD Bit, Authenticated Data)DNSSEC Signing (Zone Signing Key โ€“ ZSK, Key Signing Key โ€“ KSK)DNSSEC Rollover Procedures (KSK and ZSK Rotation)DNSSEC Deployment Challenges (Zone Size, Fragmentation, Firewall Issues)DANE (DNS-Based Authentication of Named Entities) โ€“ TLS without CAsTools (dig +dnssec, delv, ldns-verify-zone, Cloudflare DNSSEC)
WPA3 โ€“ Wi-Fi SecurityWPA2 Flaws (KRACK, Dictionary Attacks on PSK, PMKID Cracking)WPA3-Personal (SAE โ€“ Simultaneous Authentication of Equals)WPA3-Enterprise (192-bit Security Mode, EAP-TLS Mandatory)Opportunistic Wireless Encryption (OWE) โ€“ Open Wi-Fi PrivacyWPA3 Dragonfly Handshake (Derivation, Anti-Clogging Tokens)WPA3 Transition Mode (WPA2/WPA3 Mixed)Wi-Fi Enhanced Open (OWE) Use CasesWPA3 Attacks (Dragonblood Vulnerabilities, Downgrade Attacks)WPS Deprecation & Secure Configuration
OAuth โ€“ Open AuthorizationOAuth 2.0 Framework (Roles: Resource Owner, Client, Auth Server, Resource Server)OAuth 2.0 Grant Types (Auth Code, Implicit, Client Credentials, Password)OAuth Scopes (Fine-Grained Access Delegation)Access Tokens & JWT (Structure, Signing, and Validation)PKCE Implementation (Proof Key for Code Exchange)OAuth 2.0 Attacks (Redirect URI Manipulation, CSRF, Code Injection, Token Leakage)OAuth 2.0 Best Practices (Hardening and Operational Security)OAuth 2.1 (Simplified: Removed Implicit & Password Grants)
SAML โ€“ Security Assertion Markup LanguageSAML 2.0 Architecture (Identity Provider โ€“ IdP, Service Provider โ€“ SP)SAML Assertions (Authentication, Attribute, Authorization Decision)SAML Bindings (HTTP Redirect, HTTP POST, SOAP, Artifact)SAML Single Sign-On Flows (SP-Initiated vs. IdP-Initiated)SAML vs. OAuth vs. OpenID Connect (When to Use Each)SAML Signing & Encryption (XML Signature, XML Encryption)Common SAML Attacks (XML Signature Wrapping, XXE, Replay)SAML Security Best Practices (Production Hardening)
Enterprise Integration & Protocol SelectionChoosing the Right Protocol for the Job (VPN, SSO, API Auth, Wi-Fi)Protocol Stacking (TLS over IPsec, SSH over TLS โ€“ Why?)Compliance Drivers (PCI DSS, HIPAA, FedRAMP, NIST 800-63)Certificate & Key Lifecycle Management (PKI, Let's Encrypt, Vault)Legacy Protocol Deprecation (SSL, PPTP, WEP, WPA, TLS 1.0/1.1)
Real-World Protocol Exploits & MitigationsCase Study: Heartbleed (CVE-2014-0160) โ€“ TLS Memory LeakCase Study: KRACK (WPA2 Key Reinstallation Attack)Case Study: SAML XML Signature Wrapping (XSW)Case Study: OAuth Redirect URI Manipulation
Hands-On LabsLab: Generate & Validate TLS Certificates with OpenSSLLab: Test TLS Configurations Using testssl.sh & SSL LabsLab: Configure SSH Key-Based Auth & Disable PasswordsLab: Set Up a Site-to-Site IPsec VPN with StrongSwanLab: Sign a DNS Zone with DNSSEC & Validate with digLab: Capture & Analyze WPA3 Handshake (with Lab AP)Lab: Implement OAuth 2.0 Authorization Code Flow (Simulated)Lab: Build a SAML SSO Test Environment (SimpleSAMLphp)
security-protocols-standards / ssh-tooling

SSH Tools (OpenSSH, PuTTY, WinSCP, SSH-Audit)

#The Power-User's Toolkit#link

Now that we understand the architecture and hardening of SSH, we need the tools to implement and audit it. While `ssh` in the terminal is the standard, a professional security engineer uses a suite of tools to verify that their hardening is actually working.

OpenSSH: The Industry Standard

OpenSSH is the default implementation for almost all Linux/Unix systems. It's not just a client; it's a full suite including `ssh-keygen` (for keys), `ssh-copy-id` (for deployment), and `sshd` (the daemon). Mastery of the `~/.ssh/config` file is the difference between a manual admin and an efficient one.

info

๐Ÿ’ก Use the `~/.ssh/config` file to define aliases. Instead of `ssh -i ~/.ssh/id_rsa -p 2222 admin@10.0.0.5`, you can simply type `ssh prod-db`.

bash
# Example ~/.ssh/config
Host prod-web
    HostName 192.168.1.50
    User admin
    Port 2222
    IdentityFile ~/.ssh/id_ed25519
    ProxyJump jump-host

GUI Tools: PuTTY, WinSCP, and Termius

For Windows users, PuTTY was the long-time king. It provides a GUI for managing sessions and keys (`.ppk` format). WinSCP is the standard for those who prefer a 'Drag and Drop' SFTP interface over the command line. However, most of these have been superseded by the native OpenSSH client now built into Windows 10/11.

STRICT SECURE AUDIT RULE

โš ๏ธ Be cautious when importing private keys into third-party GUI tools. Ensure the tool stores the key in a secure, encrypted format and not in a plain-text temporary file.

ToolPrimary UseFormatPlatform
OpenSSHEverythingOpenSSH KeyCross-platform
PuTTYSession MgmtPPKWindows
WinSCPSFTP/GUIOpenSSH/PPKWindows
TermiusMulti-device SyncCloud/LocalCross-platform

ssh-audit: The Penetration Tester's Choice

How do you know if your `sshd_config` is actually secure? You use `ssh-audit`. This tool connects to the server and analyzes the Kex, Ciphers, and MACs. It flags everything that is 'Weak', 'Deprecated', or 'Vulnerable' based on current security standards.

Running a security audit on an SSH server
root@vulnarex:~#ssh-audit <target-ip>
  • โ–ชUse `ssh-audit` as part of your monthly compliance check
  • โ–ชStandardize on `~/.ssh/config` for all team members
  • โ–ชUse Ed25519 keys across all tools
  • โ–ชRotate host keys if a server is ever compromised
STRICT SECURE AUDIT RULE

Many 'free' SSH clients from unknown sources contain malware or key-loggers. Always use official, open-source, or widely trusted software.

quiz BLOCK (โ˜… 50 XP)

You are auditing 10 servers. You want to quickly find out if any of them are still using the deprecated `ssh-dss` algorithm. Which tool is most efficient for this?

Select your proof vectors above
challenge BLOCK (โ˜… 100 XP)

The Config Cleanup

Select your proof vectors above

Verification Proof Checkpoint

Verify exercises to earn โ˜… 160 XP and unlock next lab level.

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Checkpoints
The Power-User's Toolkit
Laboratory Sanity Code

Isolate active probes on matched virtual networks. Keep execution streams fully sandboxed.