# Security Implementation Guide

## Quick Start

This guide helps you implement the security recommendations from the UIUC security requirements evaluation.

## 📚 Documentation Structure

All security documentation is in the `docs/` directory:

1. **[UIUC_SECURITY_EXECUTIVE_SUMMARY.md](docs/UIUC_SECURITY_EXECUTIVE_SUMMARY.md)** ⭐ **START HERE**
   - Executive overview of security evaluation
   - Key findings and recommendations
   - Implementation roadmap
   - Risk assessment

2. **[UIUC_SECURITY_REQUIREMENTS.md](docs/UIUC_SECURITY_REQUIREMENTS.md)**
   - Comprehensive security requirements analysis
   - Detailed gap analysis
   - Security requirements matrix
   - Technical recommendations

3. **[SECURITY_TESTING_PLAN.md](docs/SECURITY_TESTING_PLAN.md)**
   - 100+ test case specifications
   - Automated and manual testing procedures
   - Security testing tools and setup
   - Test schedule and reporting

4. **[SECURITY_CHECKLIST.md](docs/SECURITY_CHECKLIST.md)**
   - Quick reference checklists
   - Pre-deployment security review
   - Code review security items
   - Incident response procedures

## 🚀 Quick Implementation Steps

### 1. Run Security Tests (5 minutes)

```bash
# Install test dependencies
pip install pytest pytest-asyncio pytest-cov

# Run security test suite
pytest tests/security/ -v

# Run with coverage
pytest tests/security/ --cov=src/canvas_mcp --cov-report=html
```

**Expected Results**: Some tests will pass (basic checks), some will be skipped (features not yet implemented).

### 2. Enable Automated Security Scanning (10 minutes)

The `.github/workflows/security-testing.yml` workflow is ready to use:

1. Ensure GitHub Actions is enabled for your repository
2. The workflow runs automatically on:
   - Every push to main/development
   - Every pull request
   - Weekly (Sundays)

3. Review results in the **Actions** tab

### 3. Review Current Security Status (30 minutes)

1. Read the [Executive Summary](docs/UIUC_SECURITY_EXECUTIVE_SUMMARY.md)
2. Check the security requirements matrix
3. Review the critical gaps identified
4. Prioritize implementation based on your needs

### 4. Address Critical Security Gaps (varies)

**Priority 1: Code Execution Sandboxing** (2-3 weeks)
- Implement Docker-based isolation for TypeScript execution
- See `docs/UIUC_SECURITY_REQUIREMENTS.md` Section 4.1

**Priority 2: Security Audit Logging** (1 week)
- Add logging for PII access and security events
- See `docs/UIUC_SECURITY_REQUIREMENTS.md` Section 6.1

**Priority 3: Dependency Scanning** (1 day)
- Enable Dependabot in GitHub repository settings
- Add pip-audit to CI/CD (already in workflow)

## 🧪 Testing

### Running Specific Test Categories

```bash
# FERPA compliance tests
pytest tests/security/test_ferpa_compliance.py -v

# Authentication security tests
pytest tests/security/test_authentication.py -v

# Code execution security tests
pytest tests/security/test_code_execution.py -v

# Input validation tests
pytest tests/security/test_input_validation.py -v

# Dependency security tests
pytest tests/security/test_dependencies.py -v
```

### Installing Security Testing Tools

```bash
# SAST tools
pip install bandit semgrep

# Dependency scanners
pip install pip-audit safety

# Secret detection
pip install detect-secrets

# Run SAST scan
bandit -r src/canvas_mcp/

# Run dependency scan
pip-audit

# Run secret scan
detect-secrets scan
```

## 📊 Security Metrics Dashboard

Track these metrics to monitor security posture:

| Metric | Target | Current |
|--------|--------|---------|
| Test Coverage | >80% | TBD |
| Critical Vulns | 0 | TBD |
| High Vulns | <5 | TBD |
| Tests Passing | 100% | ~60% |
| FERPA Compliance | 100% | ~70% |

Update these metrics after running the security tests.

## 🔒 Critical Security Gaps Summary

From the evaluation, these are the critical gaps requiring immediate attention:

### 1. Code Execution Sandboxing ⚠️ CRITICAL
**Current**: Code executes with full user permissions  
**Risk**: Arbitrary code execution, credential theft, system compromise  
**Solution**: Docker/VM isolation, file system restrictions, network isolation  
**Effort**: High (2-3 weeks)  
**Priority**: Critical

### 2. Security Audit Logging ⚠️ CRITICAL
**Current**: No logging of PII access or security events  
**Risk**: FERPA non-compliance, no audit trail, delayed incident detection  
**Solution**: Implement comprehensive security event logging  
**Effort**: Medium (1 week)  
**Priority**: Critical

### 3. Token Encryption ⚠️ HIGH
**Current**: API tokens stored in plaintext  
**Risk**: Token exposure if file system compromised  
**Solution**: OS credential manager integration  
**Effort**: Medium (1 week)  
**Priority**: High

### 4. PII Sanitization ⚠️ HIGH
**Current**: Logs may contain student PII  
**Risk**: FERPA compliance violation  
**Solution**: Sanitize all logs and error messages  
**Effort**: Medium (1 week)  
**Priority**: High

### 5. Security Monitoring ⚠️ MEDIUM
**Current**: No automated security monitoring  
**Risk**: Delayed threat detection  
**Solution**: Implement monitoring and alerting  
**Effort**: High (2-3 weeks)  
**Priority**: Medium

## 📋 Implementation Checklist

### Week 1-2: Critical Fixes
- [ ] Review security documentation
- [ ] Run security test suite
- [ ] Enable GitHub Actions security workflow
- [ ] Start code execution sandboxing implementation
- [ ] Enable Dependabot for dependency scanning

### Week 3-4: High Priority
- [ ] Complete code execution sandboxing
- [ ] Implement security audit logging
- [ ] Add PII sanitization to logs
- [ ] Encrypt API tokens at rest
- [ ] Complete FERPA compliance verification

### Week 5-8: Medium Priority
- [ ] Implement MCP client authentication
- [ ] Add security monitoring and alerting
- [ ] Complete all security tests
- [ ] Conduct penetration testing
- [ ] Document security procedures

### Ongoing: Continuous Improvement
- [ ] Weekly automated security scans
- [ ] Monthly security reviews
- [ ] Quarterly assessments
- [ ] Annual third-party audit

## 🆘 Getting Help

### Documentation
- **Overview**: [UIUC_SECURITY_EXECUTIVE_SUMMARY.md](docs/UIUC_SECURITY_EXECUTIVE_SUMMARY.md)
- **Requirements**: [UIUC_SECURITY_REQUIREMENTS.md](docs/UIUC_SECURITY_REQUIREMENTS.md)
- **Testing**: [SECURITY_TESTING_PLAN.md](docs/SECURITY_TESTING_PLAN.md)
- **Checklist**: [SECURITY_CHECKLIST.md](docs/SECURITY_CHECKLIST.md)

### Support
- **Security Issues**: Use [GitHub Security Advisory](https://github.com/vishalsachdev/canvas-mcp/security/advisories/new)
- **Questions**: Open GitHub issue with `security` label
- **Policy**: See [SECURITY.md](SECURITY.md)

## 📈 Success Criteria

You've successfully implemented the security plan when:

1. ✅ All critical security gaps addressed
2. ✅ Security test suite passing (>80% of tests)
3. ✅ Automated security scanning enabled
4. ✅ Zero critical vulnerabilities
5. ✅ FERPA compliance verified
6. ✅ Security documentation complete
7. ✅ Incident response plan tested
8. ✅ Regular security reviews scheduled

## 🎯 Next Actions

**Recommended order:**

1. **Today**: Read [Executive Summary](docs/UIUC_SECURITY_EXECUTIVE_SUMMARY.md) (30 min)
2. **This Week**: Run security tests and enable CI/CD workflow (1 hour)
3. **This Month**: Address critical security gaps (2-3 weeks)
4. **This Quarter**: Complete high and medium priority items (8 weeks)
5. **Ongoing**: Maintain security with regular testing and reviews

---

**Version**: 1.0  
**Last Updated**: January 2026  
**Status**: Ready for Implementation
