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Curriculum lobby
0s75 min Loop75 min★ 200 XP
Syllabus

Operating System Security

Operating System Security FundamentalsCommon OS Security Concepts (Trusted Computing Base, Security Kernel)OS Attack Surface Overview (Services, Ports, Processes, Registry/FS)Secure Installation & Baseline Configuration
User Account & Privilege ManagementPrinciple of Least Privilege (PoLP) in PracticeWindows User Accounts (Administrator vs. Standard User, UAC)Linux User Accounts (root vs. Regular User, sudo Mechanics)macOS User Accounts (Admin vs. Standard, Privacy Preferences)Group Policies & Role-Based Access Control (RBAC)
File System Permissions & Access ControlWindows NTFS Permissions (Full Control, Modify, Read & Execute)Linux/macOS POSIX Permissions (chmod, chown, umask, SUID/SGID/Sticky Bit)Access Control Lists (ACLs) – Windows icacls & Linux setfacl/getfaclShared Folder & Network Drive SecurityFile Integrity Monitoring (AIDE, Tripwire, Windows SFC)
Windows HardeningLocal Security Policy & Security Configuration WizardWindows Defender Firewall & Advanced Security RulesBitLocker Drive Encryption & TPM UsageDisabling Unnecessary Services (Print Spooler, SMBv1, RDP lockdown)Windows 10/11 Security Baselines & Microsoft Defender for EndpointWindows Registry Hardening (LSA, UAC, AutoRun)
Linux HardeningSecuring GRUB Bootloader & Single-User ModeSSH Hardening (Disable root login, key-only auth, fail2ban)AppArmor & SELinux (Enforcing/Targeted/Disabled modes)Unnecessary Package Removal & Service Disabling (systemd)iptables/nftables & TCP Wrappers/etc/security/limits.conf & PAM Configuration
macOS HardeningSystem Integrity Protection (SIP) & GatekeeperFileVault Full-Disk Encryption & Firmware PasswordmacOS Built-in Firewall & Application Firewall (pf)Privacy Settings (Camera, Microphone, Location, Accessibility)MDM Configuration Profiles & Security ConfiguratorXProtect, MRT, & Notarization
Patch Management & Update LifecycleVulnerability Lifecycle & Zero-Day RiskWindows Update (WSUS, Windows Update for Business)Linux Patch Management (apt, yum/dnf, zypper, unattended-upgrades)macOS Software Update & Nudge FrameworkThird-Party Patching (Chocolatey, Patch My PC, Munki)Testing Patches & Rollback Strategies
OS Hardening Automation & ComplianceCIS Benchmarks & DISA STIGs OverviewAutomated Hardening Scripts (PowerShell DSC, Ansible, Bash)OpenSCAP, Lynis, & Osquery for Compliance ScanningContinuous Hardening with Infrastructure as Code (IaC)
Real-World OS Attacks & DefensesWindows Privilege Escalation (Potato Attacks, PrintNightmare)Linux Privilege Escalation (Sudo Bypass, SUID Binaries, Dirty Pipe)macOS TCC Database Bypass & Persistence TechniquesDefensive Logging & Monitoring (Sysmon, Auditd, Unified Logging)
Capstone LabHarden a Windows 10 VM Against CIS Level 1Harden an Ubuntu 22.04 Server Using Lynis & SELinuxPatch Management Simulation (Identifying & Deploying Critical Patches)Post-Hardening Vulnerability Scan (Nessus/OpenVAS Comparison)
operating-system-security / defensive-logging-monitoring

Defensive Logging & Monitoring (Sysmon, Auditd, Unified Logging)

#If You Can't See the Attack, You Can't Stop It—Instrument Now#link

Post-breach, the number one failure is insufficient logging. Sysmon on Windows, auditd on Linux, and macOS Unified Logging generate the telemetry needed to detect privilege escalation, lateral movement, and persistence. This lesson teaches you to configure detailed auditing, ship logs to a SIEM, and create detection rules that catch real-world attack patterns—not just noise.

Windows Sysmon: Endpoint Telemetry Goldmine

Sysmon (System Monitor) is a Windows service that logs detailed process creation (Event ID 1), network connections (3), file creation (11), and much more. A well-tuned Sysmon configuration (e.g., SwiftOnSecurity's template) cuts noise and highlights suspicious activity. Deploy via GPO or SCCM. Use Sysmon logs to detect process hollowing, credential dumping, and lateral movement via PSExec.

Install Sysmon with a community config
root@vulnarex:~#Sysmon64.exe -accepteula -i sysmonconfig-export.xml

After installation, Event Viewer → Applications and Services Logs/Microsoft/Windows/Sysmon/Operational will populate with telemetry.

Linux Auditd: System Call Auditing for Detection

auditd can log system calls, file accesses, and user commands based on rules in /etc/audit/rules.d/. Add rules to monitor sensitive files (-w /etc/shadow -p wa), track privilege escalation (a always,exit -S execve -F euid=0), and log changes to critical configs. Use 'auditctl -l' to list rules. Ship logs to a central server using audispd plugins. Auditd is essential for detecting root actions.

bash
# Add audit rules to monitor /etc/passwd and execve as root
sudo auditctl -w /etc/passwd -p wa -k passwd_changes
sudo auditctl -a always,exit -F arch=b64 -S execve -F euid=0 -k root_commands
sudo auditctl -l   # verify rules loaded
info

💡 Use the 'ausearch' tool to query audit logs: 'ausearch -k root_commands' to see all root executions. Combine with 'aureport' for summaries.

macOS Unified Logging: Filtering the Firehose

macOS's unified logging system (log stream, log show) collects system and app logs in a single database. Use predicates to filter for security-relevant events: authorization failures, TCC denials, and process execs. Example: 'log stream --predicate 'subsystem == "com.apple.TCC"'. Forward these to a SIEM using a forwarding agent. The log data is voluminous, so precise filtering is key.

  • ▪Deploy Sysmon with a proven configuration on all Windows endpoints.
  • ▪Implement auditd rules to monitor sensitive files and privilege escalation on Linux.
  • ▪Configure macOS unified log forwarding to capture TCC denials and authorization failures.
  • ▪Ship all logs to a centralized SIEM and build correlation rules for known attack patterns.
STRICT SECURE AUDIT RULE

⚠️ Sysmon and auditd can generate massive log volumes. Plan storage and bandwidth accordingly, and use filtering to reduce noise before forwarding.

quiz BLOCK (★ 50 XP)

Which Sysmon event ID would you look for to detect a LSASS credential dump?

Select your proof vectors above
challenge BLOCK (★ 100 XP)

Logging Configuration Lab

Select your proof vectors above

Verification Proof Checkpoint

Verify exercises to earn ★ 200 XP and unlock next lab level.

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Checkpoints
If You Can't See the Attack, You Can't Stop It—Instrument Now
Laboratory Sanity Code

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