Security Awareness Training: Teaching Humans Not to Click Shit (They'll Click It Anyway)
"Nothing is true. Everything is permitted. Don't click that link. (You're going to click it, aren't you? FNORD.)"
🧠 The Problem: Humans (The Meatware Vulnerability)
Humans are the weakest link in security. Not because they're malicious—because they're predictably irrational meat computers running wetware vulnerable to social engineering exploits that predate electricity. They click links. They reuse passwords. They hold doors for strangers with badges. They want to be helpful.
Social engineering works because humans are social. Phishing works because emails look legit. USB drops work because curiosity kills. Training helps. Slightly. Are you paranoid enough yet?
ILLUMINATION: Users will click anything. Train them anyway. Then assume they clicked it. Defense in depth means assuming users are already compromised—because statistically, someone is. Our 5-10% phishing simulation click rate is realistic, not aspirational—humans are human, not security appliances. Welcome to Chapel Perilous. The paranoia is justified.
🎓 The Five Topics Everyone Needs (To Ignore Before Clicking Anyway)
1. Phishing Recognition
That email from your CEO? Not your CEO.
Training Content: Sender verification, URL inspection, urgent language red flags, attachment risks, social engineering tactics.
Real Example: "CEO" requesting wire transfer to new vendor. Verify via secondary channel (phone call, in-person).
Success Metric: >80% of phishing simulations reported within 5 minutes.
2. Password Management
Password123 is not secure. Actually use the password manager.
Required Tools: Password manager (mandatory), MFA everywhere (enforced), biometric authentication (preferred).
Standards: 16+ character passwords, unique per service, no reuse, no sharing, no sticky notes.
Success Metric: 100% MFA enrollment, password manager adoption tracking.
3. Physical Security
Don't let strangers follow you inside. Don't plug in random USBs.
Home Office Security: Lock screens when away, secure WiFi (WPA3), physical device security, visitor awareness.
Real Threats: Tailgating, USB drops (BadUSB attacks), shoulder surfing, unattended devices.
Success Metric: Zero unattended unlocked devices, physical security incident reporting.
4. Data Handling
Not everything goes to Dropbox. Understand classification.
Classification Training: Public, Low, Moderate, High, Very High, Extreme per Classification Framework.
Handling Requirements: Classify before sharing, encrypt sensitive data, use approved storage, no shadow IT.
Success Metric: >90% correct classification in knowledge checks, zero data spillage incidents.
5. Incident Reporting
Tell someone when things look weird. Early reporting limits damage.
Reporting Channels: Security incident form, direct CEO contact, incident response email, automated detection systems.
What to Report: Suspicious emails, lost devices, potential breaches, security policy violations, anomalous behavior.
Response SLA (Service Level Agreement): <30 minutes for critical incidents per Incident Response Plan.
Success Metric: >95% of suspicious activities reported, <5 minutes average report time.
CHAOS ILLUMINATION: Security training isn't about making users security experts—it's about making them aware enough to ask questions before clicking. Perfect security training produces users who question everything, including training. Teach skepticism, not blind obedience. Think for yourself, schmuck! The bureaucracy is expanding to meet the needs of the expanding bureaucracy.
🎣 Phishing Simulations: Test Reality, Measure Improvement (Spoiler: Reality Sucks)
Monthly phishing simulations with immediate feedback and zero punishment. Click = education. Report = recognition. Punishment makes people hide mistakes. Education makes people learn from them.
📊 Realistic Click Rate Expectations
Target: 5-10% click rate (realistic, not aspirational)
Why Not 0%? If click rate is 0%, simulations aren't realistic enough. Attackers use sophisticated tactics—training must match.
Measurement: Track click rates, report rates, time-to-report, repeat offenders, improvement trends.
Industry Benchmark: Average click rate 20-30%. We target <10% through continuous training.
🎭 Simulation Scenarios
Rotate realistic attack types monthly:
- CEO Fraud: Executive impersonation requesting urgent wire transfers
- IT Helpdesk: "Your password expires today" with credential phishing
- Invoice Scams: Fake vendor invoices with malicious attachments
- Credential Phishing: Fake login pages for commonly used services
- USB Drops: Physical USB devices in common areas (when applicable)
⚡ Immediate Feedback Loop
Click = instant education. Report = positive reinforcement.
Click Response: Redirect to education page explaining attack indicators, provide learning resources, no shaming.
Report Response: Confirmation message, recognition of good security behavior, contribution to security metrics.
Dashboard: Personal security score (private), organization trends (aggregated), improvement tracking.
📈 Continuous Improvement
Monthly review. Quarterly trend analysis. Annual program assessment.
Success Indicators:
- Declining click rates over time (realistic target: <10%)
- Increasing report rates (target: >80% of phishing reported)
- Decreasing time-to-report (target: <5 minutes)
- Fewer repeat offenders quarter-over-quarter
Action Threshold: >15% click rate triggers additional targeted training.
META-ILLUMINATION: Good simulations are realistic scenarios with immediate feedback and learning resources. Bad simulations are trick questions with public shaming and no follow-up. We choose education over punishment—because security culture beats security theater. Also, punishment makes people hide breaches instead of reporting them. Are you paranoid enough to question your own security assumptions?
📅 Training Frequency: Continuous, Not Annual Theater (Because Humans Forget)
Annual security training is compliance theater. People forget. Threats evolve. Training once per year is like brushing your teeth once per year—ineffective and gross. The Law of Fives applies: Five training vectors, five user types, five failure modes. Everything comes in fives if you look hard enough.
🎓 Onboarding (Day 1)
Mandatory first-day completion. 100% required before system access.
Duration: 60-90 minutes interactive training + policy acknowledgment.
Content: ISMS overview, classification framework, acceptable use, data handling, incident reporting.
Completion: Track in HR system, block system access until complete.
📅 Quarterly Refreshers (Every 3 Months)
15-minute focused modules. Four topics per year.
2025 Schedule:
- Q1: Password management & MFA best practices
- Q2: Data classification & handling procedures
- Q3: Social engineering & phishing defense
- Q4: Incident response & reporting protocols
Delivery: Scenario-based learning, real-world examples, immediate knowledge check.
🎣 Monthly Phishing Sims (Every Month)
Continuous awareness through realistic simulations.
Frequency: First Monday of every month, randomized timing.
Scenarios: Rotate through CEO fraud, IT helpdesk, invoice scams, credential phishing.
Metrics: Click rate, report rate, time-to-report, repeat offenders.
🚨 Incident-Triggered (As Needed)
Real attacks trigger organization-wide training within 24 hours.
Trigger Events: External phishing campaigns targeting Hack23, industry-specific threats, zero-day vulnerabilities affecting our stack.
Content: Real attack breakdown, indicators of compromise, reporting procedures, lessons learned.
SLA: Training deployed <24 hours after incident identification.
👨💻 Role-Specific (Varies by Role)
Different roles = different threats = different training.
Developers: Secure coding (monthly), secrets management (quarterly), supply chain security (semi-annual).
CEO/Management: BEC defense (quarterly), wire transfer fraud (semi-annual), regulatory compliance (annual).
Everyone: Core security awareness + role-specific threats.
ILLUMINATION: Training once and expecting permanent behavior change is optimistic. Humans forget. Threats evolve. Train continuously or accept continuous risk. Annual training is security theater—continuous training is security culture. You are now in Chapel Perilous. Security training both works and doesn't work. Both are true.
📋 Hack23's Continuous Training Framework (Reality-Based, Not Fantasy)
Security awareness at Hack23 is continuous, role-specific, and measurement-driven. Our training program is documented in our Information Security Policy as an integrated component of our ISMS—because training isn't a checkbox, it's a culture.
🎓 Onboarding: Baseline for All
Mandatory first-day training. 100% completion required.
Topics: ISMS overview, classification framework, acceptable use, incident reporting, data handling, access control basics.
Delivery: Interactive modules + policy acknowledgment + initial phishing baseline test.
New hires complete security training before system access. No exceptions. Trust starts with education. Or more accurately: distrust starts with realistic assessment of human fallibility.
📅 Quarterly Modules: Focused Deep Dives
15-minute targeted training sessions. Four topics per year.
2025 Schedule: Q1 - Password management & MFA; Q2 - Data classification & handling; Q3 - Social engineering & phishing; Q4 - Incident response & reporting.
Format: Scenario-based learning, real-world examples, immediate knowledge check.
Short, frequent training beats annual marathon sessions. Humans forget. Train continuously. FNORD.
🎣 Monthly Phishing Simulations
Realistic scenarios. Immediate feedback. No punishment.
Target Click Rate: 5-10% (realistic expectation, not aspirational zero).
Scenarios: CEO fraud, IT helpdesk impersonation, invoice scams, credential phishing, USB drops.
Response: Click = immediate education module. Report = positive reinforcement.
0% click rate means unrealistic simulations. 5-10% means effective training that mirrors real threats. Perfect scores indicate broken tests, not perfect humans.
🚨 Incident-Triggered Training
Real phishing campaign detected? Everyone trains immediately.
Trigger: Any external phishing campaign targeting Hack23 triggers organization-wide training within 24 hours.
Content: Real attack breakdown, indicators, reporting procedures, lessons learned.
Learn from actual attacks in real-time. Attackers provide free training content—use it. Every breach is a teachable moment. Every phishing campaign is intelligence gathering.
👨💻 Role-Specific Content
Developers ≠ Finance ≠ Executives. Training reflects reality.
Developers: Secure coding, secrets management, code review, supply chain security.
CEO/Management: Business email compromise, executive impersonation, wire transfer fraud, regulatory compliance.
Everyone: Core security awareness + role-specific threats.
Generic training produces generic awareness. Role-specific training produces relevant behavior changes. Or at least, that's the theory. Reality is messier. Always.
📊 Metrics-Driven Improvement
Track everything. Improve what matters.
Metrics: Training completion rates, phishing simulation click rates, time-to-report, incident frequency, knowledge check scores.
Reporting: Monthly dashboard review, quarterly trend analysis, annual program assessment.
Target: >95% completion, 5-10% click rate, <5 minutes report time, declining incident trend.
META-ILLUMINATION: Perfect security training produces users who question everything, including training. Teach skepticism, not blind obedience. You are now leaving Chapel Perilous. Or entering it. Hard to tell which. The paranoia is the point.
🎯 Conclusion: Train, Test, Measure, Repeat (Welcome to Sisyphus's Security Department)
Humans will never be perfect security controls. They'll click links. They'll reuse passwords. They'll hold doors. Train them anyway. Because the alternative is worse. Probably. Nothing is certain except entropy and exploitable humans.
Security awareness training isn't about eliminating human error—it's about reducing it enough that other controls can compensate. Defense in depth includes educated users who: (1) fail slightly less often, (2) report failures faster, (3) question suspicious requests occasionally. Low bar? Yes. Realistic? Also yes.
- Recognize phishing with >80% accuracy and <5 minute report time
- Use password managers with 100% MFA enrollment and unique passwords
- Handle data correctly with >90% classification accuracy and zero spillage
- Report incidents promptly with >95% suspicious activity reporting
- Question suspicious requests before acting, especially urgent wire transfers
Our training framework: Onboarding (mandatory) + Quarterly modules (focused) + Monthly phishing sims (realistic) + Incident-triggered (timely) + Role-specific (relevant) + Metrics-driven (measurable).
Train continuously. Test regularly. Measure rigorously. Don't punish mistakes—learn from them. And assume users are compromised anyway, because eventually they will be. That's why defense in depth includes both educated users AND compensating controls. Trust no one. Not even yourself. Especially not yourself.
Training metrics we actually track:
- 📊 Training completion: >95% target for all mandatory modules
- 🎣 Phishing click rate: 5-10% realistic target (not aspirational 0%)
- 📢 Report rate: >80% of phishing simulations reported
- ⏱️ Time-to-report: <5 minutes average for suspicious activities
- 📈 Improvement trend: Declining click rates, increasing report rates quarter-over-quarter
Full training framework integrated into our Information Security Policy—because security through transparency means documenting how we actually train humans, not how we claim to. Reality > marketing. All documentation is propaganda. This propaganda happens to be true. Probably.
All hail Eris! All hail Discordia!
"Think for yourself, schmuck! Question everything—especially that urgent email from your boss asking for wire transfers to an unfamiliar account. Are you paranoid enough?"
🍎 23 FNORD 5
— Hagbard Celine, Captain of the Leif Erikson
P.S. You are now in Chapel Perilous. Security training both works and doesn't work. Both are true. Users are both educated and exploitable. Nothing is true. Everything is permitted—except clicking suspicious links. (But you'll click them anyway. We know. We measure. 5-10%. Statistically inevitable. FNORD.)