Cyber Insurance Readiness Checklist for SMBs

The 12 controls underwriters check in 2025 ยท Evidence requirements ยท 90/60/30-day renewal timeline

Tier 1 โ€” Non-negotiable
These three controls determine whether you get a quote at all

โœ“ControlWhat to show the underwriter
1MFA enforced on email, VPN, and all privileged accounts
Microsoft 365, Google Workspace, VPN, cloud admin โ€” hardware key or authenticator app preferred over SMS. Break-glass accounts excluded from MFA are a leading decline reason.
Conditional Access / MFA policy screenshots
User enrollment report
Service account coverage list
IMAP/POP disabled proof
2EDR deployed on 100% of devices โ€” servers and workstations, all OS
Behavioral detection, containment, rollback. Legacy antivirus does not qualify. Coverage gaps on Macs, Linux, or contractor devices get flagged in the policy.
EDR console coverage report
Agents installed and healthy across all devices
Policy configuration screenshots
30โ€“90 day alert metrics
3Immutable / offline backups with quarterly tested restores
Cloud sync (OneDrive, Dropbox) does not count. Object-locked cloud storage, air-gapped media, or vaulted storage with documented test restore results.
Backup topology diagram
Immutability policy settings
Last 3 months of successful job logs
Quarterly test restore report

Tier 2 โ€” Required with slightly more flexibility
Gaps can trigger conditions, sublimits, or increased deductibles

โœ“ControlWhat to show the underwriter
4Security awareness training โ€” quarterly minimum with phishing simulations. Monthly click-rate data and evidence of remedial training for repeat clickers.Training completion rates (12 months)
Phishing simulation results with click rate trend
Incident reporting procedure training records
5Email security โ€” SPF/DKIM/DMARC configured, anti-impersonation controls, external email banner/tagging.Email security policy screenshots
DMARC enforcement records
Impersonation protection config
6Patch management โ€” documented SLAs: critical within 48โ€“72h, high-risk within 7 days, all others within 30 days. Legacy OS in production gets flagged and may be excluded.RMM patch compliance reports
Vulnerability scan summaries with trend lines
Change tickets showing remediation
7Privileged access management โ€” separate admin accounts for privileged tasks, local admin rights removed from standard users, password vaulting for shared credentials and service accounts.Privileged group membership reports
Password vault configuration
Service account inventory
8Remote access hardening โ€” no open RDP exposed to the internet. VPN or ZTNA with MFA enforced. SMBv1 disabled. Geo-IP allow-listing in place.External attack surface scan proving no open RDP
VPN or ZTNA configuration documentation
Firewall rule exports

Tier 3 โ€” Documentation-heavy
Proof-of-work items that separate smooth renewals from last-minute scrambling

โœ“ControlWhat to show the underwriter
9Written IR plan tested via tabletop exercise in the last 12 months โ€” clear roles, decision trees, pre-identified legal counsel and breach coach contacts.Written IR playbook
Tabletop exercise after-action report (within 12 months)
Vendor panel list with pre-negotiated forensics contacts
10Centralized logging with 24/7 monitoring / SOC โ€” evidence someone is watching the environment around the clock, not just during business hours.SIEM or MDR onboarding documentation
Dashboard screenshot showing ingest volume and active detections
11Encryption at rest โ€” full-disk encryption on laptops and servers. Often assumed but carriers want confirmation it's enabled.FDE status screenshots on all devices
Policy confirming FDE requirement enforcement
12Vendor / third-party risk management โ€” vendor inventory with criticality ratings, security posture reviews, contractual breach notification clauses.Vendor inventory with criticality ratings
Security review records
Contract breach notification clauses

Application Red Flags
The fastest way to get declined, surcharged, or written with conditions

No MFA on email or VPN โ€” instant decline or heavy sublimits in most cases.
Legacy OS (Server 2012, etc.) in production โ€” carrier may exclude those systems from coverage entirely.
Backups accessible over domain credentials โ€” ransomware can reach them. Carriers know this and check.
EDR coverage gaps (Macs, Linux, contractor devices) โ€” policy written with device count exclusions.
No IR plan, or plan not tested in last 12 months โ€” underwriter assumes no response capability.
Application doesn't match actual tool inventory โ€” misrepresentation is the #1 cause of claim denial.
No evidence of backup testing โ€” carrier assumes backups are non-functional until proven otherwise.

Renewal Prep Timeline

๐Ÿ“… 90 Days Out

๐Ÿ“… 60 Days Out

๐Ÿ“… 30 Days Out