Small Business Cyber Security Checklist: Meet Insurance Requirements
🔒SECURITY ESSENTIALS
Cyber insurance carriers are no longer accepting basic security measures. Here's the comprehensive checklist to meet 2024 requirements and protect your business—even if you're not applying for insurance yet.
🎯 Tier 1: Minimum Requirements (Every Business)
⚠️ Without These, You Won't Get Coverage
🔐 Multi-Factor Authentication (MFA)
Required on ALL admin accounts, email systems, cloud services, and remote access
💾 Immutable Backups
Backups that can't be encrypted by ransomware (offline or write-once storage)
🔄 Regular Security Updates
Operating systems and critical software patched within 30 days
🛡️ Business-Grade Antivirus/EDR
Beyond basic Windows Defender—need managed detection and response
🔐 MFA Implementation Guide
✅ MFA Deployment Checklist
📧 Email Systems
✅ Office 365/Google Workspace admin accounts
✅ All user email accounts (if possible)
✅ Email forwarding rules protected
Priority: Critical - attackers target email first
☁️ Cloud Services
✅ AWS/Azure admin consoles
✅ Business-critical SaaS applications
✅ File sharing services (Dropbox, OneDrive)
Priority: Critical - contains business data
🖥️ Network Access
✅ VPN connections
✅ Remote desktop access
✅ Network device management
Priority: Critical - prevents lateral movement
💼 Business Applications
✅ Accounting software
✅ Customer database access
✅ Payment processing systems
Priority: High - contains sensitive data
💾 Backup Strategy That Actually Works
💾 3-2-1-1 Backup Rule for Business
3
Copies of Data
Original + 2 backups
2
Different Media Types
Disk + cloud/tape
1
Offsite Location
Cloud or physical offsite
1
Immutable Copy
Can't be encrypted
🎯 Small Business Implementation
Daily: Automated backup to cloud storage (OneDrive, Google Drive, AWS S3)
Weekly: Full backup to external drive stored offsite or in fireproof safe
Monthly: Test restore process - actually recover files to verify backups work
Quarterly: Full disaster recovery test - restore entire system from backup
Weekly: Full backup to external drive stored offsite or in fireproof safe
Monthly: Test restore process - actually recover files to verify backups work
Quarterly: Full disaster recovery test - restore entire system from backup
🔧 Tier 2: Preferred Requirements (Better Rates)
💰 These Get You Premium Discounts (10-20%)
👨🎓 Security Awareness Training
What it is: Monthly training with phishing simulation (KnowBe4, Proofpoint, etc.)
Why carriers care: 95% of breaches start with human error
Implementation: 30 minutes/month per employee + quarterly phishing tests
Why carriers care: 95% of breaches start with human error
Implementation: 30 minutes/month per employee + quarterly phishing tests
🔍 Vulnerability Scanning
What it is: Regular scans of your network for security weaknesses
Why carriers care: Shows proactive security management
Implementation: Quarterly scans + remediation tracking
Why carriers care: Shows proactive security management
Implementation: Quarterly scans + remediation tracking
📋 Written Security Policies
What it is: Documented cybersecurity program and incident response plan
Why carriers care: Demonstrates mature security posture
Implementation: Templates available from NIST, industry associations
Why carriers care: Demonstrates mature security posture
Implementation: Templates available from NIST, industry associations
🌐 Network Segmentation
What it is: Separate critical systems from general network access
Why carriers care: Limits damage from successful attacks
Implementation: VLANs or physical separation for sensitive data
Why carriers care: Limits damage from successful attacks
Implementation: VLANs or physical separation for sensitive data
🏆 Tier 3: Premium Requirements (Best Rates)
🌟 Enterprise-Grade Controls (20-30% Discounts)
🔒 Zero Trust Architecture
"Never trust, always verify" - every access request is authenticated and authorized
🎯 24/7 Security Monitoring (SOC)
Professional security team monitoring your environment around the clock
📊 NIST Framework Alignment
Documented alignment with NIST Cybersecurity Framework with annual assessments
🔍 Annual Penetration Testing
Third-party security testing to identify vulnerabilities before attackers do
💰 Quick Wins: High Impact, Low Cost
⚡ Implement These First (Under $500/Month)
🏢 Microsoft 365 Business Premium
Cost: $22/user/month
Includes: MFA, basic threat protection, device management
Insurance impact: Meets most basic requirements
🎓 KnowBe4 Security Training
Cost: $4-8/user/month
Includes: Training + phishing simulation
Insurance impact: 10-15% premium discount
☁️ Cloud Backup Service
Cost: $50-200/month
Includes: Automated backups + immutable storage
Insurance impact: Required for coverage
🛡️ Managed EDR Service
Cost: $10-25/endpoint/month
Includes: 24/7 monitoring + incident response
Insurance impact: 15-20% premium discount
📋 90-Day Implementation Timeline
📅 Phased Security Implementation
🚀 Days 1-30: Foundation
✅ Enable MFA on all admin accounts
✅ Set up automated backups
✅ Install business-grade antivirus/EDR
✅ Update all critical systems
✅ Create inventory of all systems and data
✅ Set up automated backups
✅ Install business-grade antivirus/EDR
✅ Update all critical systems
✅ Create inventory of all systems and data
📈 Days 31-60: Enhancement
✅ Deploy security awareness training
✅ Implement network monitoring
✅ Create incident response plan
✅ Test backup recovery process
✅ Conduct vulnerability assessment
✅ Implement network monitoring
✅ Create incident response plan
✅ Test backup recovery process
✅ Conduct vulnerability assessment
🏆 Days 61-90: Optimization
✅ Document all security policies
✅ Implement network segmentation
✅ Set up security monitoring dashboard
✅ Conduct tabletop exercises
✅ Apply for cyber insurance with confidence
✅ Implement network segmentation
✅ Set up security monitoring dashboard
✅ Conduct tabletop exercises
✅ Apply for cyber insurance with confidence
🎯 Remember: Security First, Insurance Second
These security measures protect your business whether you have cyber insurance or not. The insurance is just financial backstop—your real protection comes from making your business a harder target for cybercriminals.