Cyber insurance readiness for businesses

Cyber Insurance Readiness Checklist for Businesses

Review security controls, technical evidence, documentation, ownership, and remediation priorities before a cyber insurance application, renewal, or insurer follow-up.

150Readiness review items organized by security and governance domain
16Checklist sections for application and renewal preparation
25+Years cybersecurity, infrastructure, Microsoft, and Cisco experience
OCBuilt for Irvine, Orange County, Los Angeles County, and Southern California
Application and renewal preparation

Organize the controls and evidence behind your questionnaire responses.

Cyber insurance questionnaires often ask for detailed information about MFA, endpoint security, privileged accounts, backups, patching, firewalls, VPN access, email protection, cloud services, incident response, business continuity, security awareness, and supporting documentation.

This checklist helps authorized stakeholders review those areas methodically before information is submitted. It is built for business owners, CEOs, CFOs, IT managers, internal IT teams, security leaders, compliance personnel, and other authorized representatives.

Business ownersCEOs and CFOsIT managersInternal IT teamsSecurity leadersAuthorized personnel

This checklist is for initial readiness guidance only and does not replace a professional cybersecurity audit, legal review, insurance broker guidance, insurer underwriting decision, or formal compliance assessment.

Cyber insurance readiness program with controls and evidence review
Readiness focus

What insurers commonly expect to see backed by evidence

Identity and MFA

Review MFA coverage for business email, Microsoft 365, administrators, VPN, cloud apps, privileged accounts, and third-party access.

  • Conditional Access and MFA reports
  • Privileged role review
  • Legacy authentication restrictions

Endpoint and EDR

Confirm endpoint protection, EDR/MDR coverage, patch status, local admin controls, device inventory, and response visibility.

  • EDR deployment evidence
  • Patch and vulnerability reports
  • Endpoint hardening baseline

Backups and Recovery

Validate backup scope, immutable or protected backups, restore testing, retention, ransomware recovery, and business continuity documentation.

  • Backup job and restore records
  • Recovery time expectations
  • Incident recovery procedure

Email and Microsoft 365

Review anti-phishing, SPF, DKIM, DMARC, mailbox forwarding, audit logs, SharePoint/OneDrive sharing, and risky sign-in visibility.

Network and Firewall

Review firewall rules, VPN exposure, remote access, segmentation, DNS filtering, logging, and externally exposed services.

Governance and Evidence

Organize ownership, policy records, exceptions, remediation plans, validation dates, screenshots, exports, and approval records.

Cyber insurance readiness workbook

Technical control checklist

Review each control, suggested evidence item, and priority level. The status, owner, target date, and notes areas are intentionally displayed as blank gray reference fields. Scroll horizontally and vertically inside the checklist area to review all columns and items.

150Total items
StaticRead-only checklist
Cyber insurance application and renewal readiness review for authorized internal use.
ID Control or Review Item Suggested Evidence Status Priority Owner Target Date Notes, Evidence Reference, Exception, or Remediation Detail
AGovernance, Scope & Accountability
A-01 Identify the executive sponsor responsible for cyber insurance readiness. Named executive sponsor and approval record Not Reviewed High
A-02 Assign a primary technical owner for questionnaire responses and evidence collection. Owner list, escalation path, project tracker Not Reviewed High
A-03 Confirm the legal business name, locations, employee count, and covered entities. Corporate records and policy application scope Not Reviewed Medium
A-04 Document critical business operations, revenue-impacting services, and operational dependencies. Business-impact notes and dependency map Not Reviewed High
A-05 Identify regulated, confidential, financial, health, customer, and employee data handled by the business. Data classification summary Not Reviewed High
A-06 Document internal IT staff, MSP, MSSP, cloud providers, and other technology vendors. Vendor list with responsibilities Not Reviewed Medium
A-07 Confirm the insurance application or renewal deadline and any broker follow-up dates. Timeline and submission calendar Not Reviewed High
A-08 Store the insurer questionnaire, prior responses, endorsements, and requested evidence in a controlled location. Controlled document repository Not Reviewed High
BQuestionnaire Accuracy & Evidence Readiness
B-01 Review every questionnaire response against the current technical environment before submission. Completed response review and sign-off Not Reviewed Critical
B-02 Avoid unsupported answers, assumptions, or blanket statements that cannot be validated. Evidence references attached to responses Not Reviewed Critical
B-03 Identify responses that require clarification from the insurer or broker. Clarification log Not Reviewed Medium
B-04 Maintain screenshots, configuration exports, reports, policies, and supporting records for material controls. Evidence index Not Reviewed High
B-05 Record the date each control was validated and the person who validated it. Validation register Not Reviewed Medium
B-06 Document exceptions, compensating controls, planned remediation, and target dates. Exception and remediation log Not Reviewed High
B-07 Confirm that answers are consistent across the application, supporting documents, and internal records. Final quality-control review Not Reviewed Critical
B-08 Retain a final approved copy of the submitted questionnaire and supporting materials. Submission archive Not Reviewed High
CIdentity, MFA & Access Control
C-01 Enforce multi-factor authentication for Microsoft 365 and business email users. MFA coverage report Not Reviewed Critical
C-02 Enforce MFA for administrator, privileged, and emergency access accounts. Privileged-account MFA evidence Not Reviewed Critical
C-03 Enforce MFA for VPN, remote-access tools, and remote desktop gateways. VPN and remote-access settings Not Reviewed Critical
C-04 Enforce MFA for cloud applications that store sensitive or business-critical information. Cloud application inventory and MFA report Not Reviewed High
C-05 Require strong authentication for third-party vendors and support providers. Vendor-access review Not Reviewed High
C-06 Disable or restrict legacy authentication protocols that bypass modern controls. Legacy-authentication report Not Reviewed High
C-07 Review inactive, dormant, duplicate, and former-employee accounts. Account cleanup report Not Reviewed High
C-08 Use role-based access and least-privilege principles for users and groups. Access matrix and group review Not Reviewed High
C-09 Review service accounts, shared accounts, and application credentials. Service-account inventory Not Reviewed High
C-10 Document onboarding, role-change, and offboarding procedures. Access lifecycle procedure Not Reviewed Medium
C-11 Review password policies, lockout settings, and self-service password reset controls. Identity policy export Not Reviewed Medium
C-12 Periodically review access for critical systems, cloud platforms, and sensitive data repositories. Access-review records Not Reviewed High
DPrivileged Access Management
D-01 Maintain a current inventory of domain, cloud, network, firewall, server, and application administrators. Privileged-account inventory Not Reviewed Critical
D-02 Separate daily-use accounts from privileged administrator accounts. Account naming standard and account list Not Reviewed High
D-03 Restrict privileged access to authorized personnel with documented business need. Approval records and role assignments Not Reviewed High
D-04 Review global administrator roles in Microsoft 365 and Azure. Role-assignment report Not Reviewed Critical
D-05 Use dedicated administrative workstations or hardened access paths where appropriate. Administrative-access procedure Not Reviewed Medium
D-06 Log and review privileged actions on critical systems. Audit log configuration and review records Not Reviewed High
D-07 Protect emergency or break-glass accounts with documented controls and monitoring. Emergency-account procedure Not Reviewed High
D-08 Remove unnecessary local administrator rights from endpoints. Endpoint privilege report Not Reviewed High
EMicrosoft 365 & Email Security
E-01 Review Microsoft Entra ID security settings and Conditional Access policies. Conditional Access export Not Reviewed Critical
E-02 Review Exchange Online anti-phishing, anti-spam, and anti-malware protections. Email-security policy export Not Reviewed High
E-03 Configure and validate SPF, DKIM, and DMARC for business domains. DNS records and DMARC validation Not Reviewed High
E-04 Review automatic forwarding, mailbox rules, delegated access, and suspicious inbox activity. Mailbox-rule and forwarding report Not Reviewed High
E-05 Review external sharing settings for SharePoint, OneDrive, and Teams. Sharing configuration report Not Reviewed High
E-06 Enable and retain appropriate audit logs for identity, email, collaboration, and administrative activities. Audit-log settings and retention evidence Not Reviewed High
E-07 Review risky users, risky sign-ins, impossible travel, and suspicious login activity. Identity protection review Not Reviewed High
E-08 Review administrator roles, app registrations, enterprise applications, and OAuth consent. Application and role inventory Not Reviewed High
E-09 Confirm appropriate licensing and security tooling for the organization’s risk profile. License and security-tool inventory Not Reviewed Medium
E-10 Document email incident response steps for phishing, compromised accounts, and fraudulent payment requests. Email incident playbook Not Reviewed High
FEndpoint Security, EDR & Device Control
F-01 Maintain an accurate inventory of workstations, laptops, servers, and mobile devices. Device inventory Not Reviewed High
F-02 Deploy antivirus and endpoint detection and response protection to supported endpoints. EDR coverage report Not Reviewed Critical
F-03 Review endpoints that are offline, unmanaged, unsupported, or missing protection. Coverage exception report Not Reviewed Critical
F-04 Monitor endpoint alerts and document the escalation process. Alert-handling procedure Not Reviewed High
F-05 Apply disk encryption to laptops and other portable devices that store business data. Encryption compliance report Not Reviewed High
F-06 Restrict unauthorized software installation and risky browser extensions where appropriate. Application-control settings Not Reviewed Medium
F-07 Review local administrator privileges and remove unnecessary elevated access. Local admin review Not Reviewed High
F-08 Use screen locking, secure configurations, and device hardening standards. Endpoint baseline documentation Not Reviewed Medium
F-09 Document lost-device, stolen-device, and remote-wipe procedures. Mobile-device incident procedure Not Reviewed Medium
F-10 Retire or isolate unsupported operating systems and obsolete devices. Lifecycle and replacement plan Not Reviewed High
GPatching & Vulnerability Reduction
G-01 Document a patch-management process for operating systems, applications, servers, and network devices. Patch-management procedure Not Reviewed High
G-02 Apply critical security updates within defined risk-based timelines. Patch compliance reports Not Reviewed Critical
G-03 Track exceptions for systems that cannot be patched promptly. Exception register and compensating controls Not Reviewed High
G-04 Perform recurring vulnerability scans for internal and internet-facing assets. Recent vulnerability scan reports Not Reviewed High
G-05 Prioritize remediation by severity, exploitability, exposure, and business impact. Remediation tracker Not Reviewed High
G-06 Update firewall, router, switch, wireless, VPN, and security-appliance firmware. Firmware inventory and update records Not Reviewed High
G-07 Review unsupported software, end-of-life systems, and obsolete applications. Technology lifecycle inventory Not Reviewed High
G-08 Validate remediation of high-risk findings with rescans or follow-up review. Closure evidence Not Reviewed High
G-09 Track externally exposed services and remove unnecessary exposure. External attack-surface inventory Not Reviewed Critical
G-10 Document vulnerability ownership, deadlines, and escalation procedures. Remediation governance record Not Reviewed Medium
HFirewall, VPN, Network & Remote Access
H-01 Maintain a current network diagram showing firewalls, routers, switches, wireless networks, VPNs, and major systems. Current network diagram Not Reviewed High
H-02 Review firewall rules and remove obsolete, duplicate, broad, or unnecessary access. Firewall-rule review report Not Reviewed Critical
H-03 Review NAT rules, port forwarding, public IP exposure, and published services. External exposure inventory Not Reviewed Critical
H-04 Restrict remote desktop exposure and avoid direct internet-facing RDP access. Remote-access validation Not Reviewed Critical
H-05 Require secure VPN or controlled remote-access methods with MFA. VPN configuration evidence Not Reviewed Critical
H-06 Review third-party vendor remote access and limit it by business need. Vendor remote-access register Not Reviewed High
H-07 Enable firewall logging, alerting, and periodic review. Firewall logging configuration Not Reviewed High
H-08 Use network segmentation for sensitive systems, servers, backups, and critical operations where appropriate. Segmentation diagram and rule review Not Reviewed High
H-09 Review wireless security, guest access, encryption standards, and administrative passwords. Wireless configuration review Not Reviewed Medium
H-10 Change default credentials and restrict management interfaces on network devices. Network-device hardening checklist Not Reviewed High
H-11 Review DNS filtering, web filtering, and protective gateway controls where used. Gateway-security settings Not Reviewed Medium
H-12 Document firewall changes, approvals, and periodic recertification. Change-management records Not Reviewed Medium
IBackup, Recovery & Business Continuity
I-01 Identify systems, applications, cloud services, and data that require backup or recovery planning. Backup scope inventory Not Reviewed Critical
I-02 Maintain protected backups with appropriate isolation from production credentials and ransomware exposure. Backup architecture and access review Not Reviewed Critical
I-03 Use offsite, immutable, offline, or logically separated backup options where appropriate. Backup protection evidence Not Reviewed Critical
I-04 Restrict backup-administration access and require strong authentication. Backup admin account review Not Reviewed High
I-05 Document backup frequency, retention, and recovery objectives. Backup policy and schedule Not Reviewed High
I-06 Perform recurring restore tests and retain the results. Restore-test records Not Reviewed Critical
I-07 Confirm that Microsoft 365, cloud workloads, databases, and line-of-business systems are addressed. Application recovery matrix Not Reviewed High
I-08 Document recovery priorities for critical systems and business processes. Recovery-priority list Not Reviewed High
I-09 Maintain business-continuity procedures for major outages, ransomware, and technology failures. Business-continuity plan Not Reviewed High
I-10 Review backup monitoring, failed-job alerts, storage capacity, and escalation procedures. Backup-monitoring report Not Reviewed High
I-11 Protect backup documentation and recovery credentials in a controlled location. Recovery documentation register Not Reviewed Medium
I-12 Review recovery dependencies such as internet connectivity, hardware, licensing, vendors, and facility access. Dependency checklist Not Reviewed Medium
JIncident Response & Ransomware Readiness
J-01 Maintain a written incident response plan with roles, contacts, and escalation procedures. Incident response plan Not Reviewed Critical
J-02 Define the process for isolating affected systems, disabling accounts, and preserving evidence. Containment playbook Not Reviewed Critical
J-03 Document ransomware response steps, recovery priorities, and executive decision paths. Ransomware playbook Not Reviewed Critical
J-04 Maintain current contact information for leadership, IT, legal counsel, broker, carrier, vendors, and forensic resources. Incident contact list Not Reviewed High
J-05 Define internal and external communication procedures for suspected incidents. Communication plan Not Reviewed High
J-06 Conduct periodic tabletop exercises for realistic incident scenarios. Tabletop agenda and after-action report Not Reviewed High
J-07 Train employees to report suspicious activity quickly. Reporting procedure and training records Not Reviewed Medium
J-08 Define evidence-preservation procedures for logs, devices, email, and cloud systems. Evidence-preservation checklist Not Reviewed High
J-09 Document lessons learned and remediation actions after security events. Post-incident review records Not Reviewed Medium
J-10 Review cyber insurance notification requirements with qualified insurance and legal advisors. Notification contact sheet and advisory notes Not Reviewed High
KLogging, Monitoring & Threat Detection
K-01 Identify security-relevant logs for firewalls, VPNs, endpoints, servers, identity platforms, email, and cloud services. Logging inventory Not Reviewed High
K-02 Retain logs for an appropriate period based on operational, investigative, and contractual needs. Retention configuration Not Reviewed High
K-03 Monitor endpoint and security alerts and document response expectations. Monitoring and escalation procedure Not Reviewed High
K-04 Review failed logins, anomalous access, risky sign-ins, and privileged activity. Periodic security review records Not Reviewed High
K-05 Review firewall, VPN, and remote-access logs for suspicious activity. Network-log review records Not Reviewed High
K-06 Centralize logs or use SIEM capabilities where appropriate for the environment. SIEM or centralized logging evidence Not Reviewed Medium
K-07 Protect logs from unauthorized modification or deletion. Log-access controls Not Reviewed Medium
K-08 Define alert severity, ownership, escalation timing, and documentation requirements. Alert matrix Not Reviewed Medium
LData Protection & Encryption
L-01 Identify sensitive data locations across servers, endpoints, cloud platforms, email, and third-party systems. Data-location inventory Not Reviewed High
L-02 Use encryption for sensitive data in transit and at rest where appropriate. Encryption settings and validation Not Reviewed High
L-03 Apply laptop and portable-device encryption. Device encryption compliance report Not Reviewed High
L-04 Restrict access to sensitive file shares, databases, and cloud repositories. Permissions review Not Reviewed High
L-05 Review external sharing, guest access, public links, and file-transfer practices. External sharing report Not Reviewed High
L-06 Document secure data retention and disposal procedures. Retention and disposal policy Not Reviewed Medium
L-07 Review removable-media controls and portable-storage risks. Removable-media procedure Not Reviewed Medium
L-08 Document data-breach escalation paths and affected-data assessment steps. Data incident procedure Not Reviewed High
MVendor, MSP & Third-Party Risk
M-01 Maintain a list of MSPs, MSSPs, cloud providers, software vendors, payment providers, and critical third parties. Third-party inventory Not Reviewed High
M-02 Document which vendors access systems, networks, cloud platforms, or sensitive data. Vendor access matrix Not Reviewed High
M-03 Require appropriate authentication and least-privilege access for vendors. Vendor access-control review Not Reviewed High
M-04 Remove inactive vendor accounts and review shared support credentials. Vendor-account cleanup report Not Reviewed High
M-05 Review contracts for security responsibilities, incident notification, and support expectations. Contract review notes Not Reviewed Medium
M-06 Document how third-party incidents will be reported, escalated, and coordinated. Vendor incident procedure Not Reviewed Medium
M-07 Periodically review critical vendors based on data access and operational dependency. Vendor review schedule Not Reviewed Medium
M-08 Document backup, recovery, and continuity dependencies involving vendors. Vendor continuity checklist Not Reviewed Medium
NSecurity Awareness & Workforce Controls
N-01 Provide recurring security-awareness training for employees. Training records Not Reviewed High
N-02 Include phishing, password safety, MFA fatigue, suspicious links, payment fraud, and reporting procedures. Training curriculum Not Reviewed High
N-03 Provide role-specific guidance for executives, finance staff, administrators, and employees handling sensitive data. Role-based training records Not Reviewed Medium
N-04 Document onboarding and offboarding security steps. HR and IT checklist Not Reviewed High
N-05 Review employee reporting channels for suspected phishing, lost devices, and suspicious activity. Reporting instructions Not Reviewed Medium
N-06 Conduct phishing-awareness exercises where appropriate. Exercise summary and remediation notes Not Reviewed Medium
N-07 Require employees to acknowledge acceptable-use and security policies. Policy acknowledgment records Not Reviewed Medium
N-08 Train finance and leadership teams on business email compromise and payment-change verification. Finance fraud-prevention procedure Not Reviewed High
OCloud, Azure & Hosted Systems
O-01 Maintain an inventory of Azure, cloud, SaaS, hosted, and externally managed systems. Cloud-service inventory Not Reviewed High
O-02 Review cloud administrator roles, MFA coverage, privileged access, and guest accounts. Cloud identity review Not Reviewed Critical
O-03 Review exposed workloads, public IPs, storage, databases, and internet-facing services. Cloud exposure report Not Reviewed Critical
O-04 Review cloud logging, monitoring, alerting, and retention settings. Cloud logging evidence Not Reviewed High
O-05 Review storage permissions, public access, encryption, and data-sharing settings. Cloud storage review Not Reviewed High
O-06 Document backup and recovery arrangements for cloud workloads and SaaS data. Cloud recovery matrix Not Reviewed High
O-07 Review third-party integrations, service principals, application registrations, and secrets. Integration inventory Not Reviewed High
O-08 Apply secure configuration baselines and document remediation for material findings. Cloud hardening checklist Not Reviewed Medium
PPolicies, Documentation & Final Review
P-01 Maintain written policies for access control, passwords, MFA, acceptable use, patching, backups, incident response, and business continuity. Policy library Not Reviewed High
P-02 Maintain current inventories for users, devices, servers, applications, vendors, cloud services, and network equipment. Inventory records Not Reviewed High
P-03 Maintain current network diagrams and data-flow or dependency diagrams where needed. Architecture documentation Not Reviewed Medium
P-04 Document security exceptions, compensating controls, owners, deadlines, and remediation status. Exception register Not Reviewed High
P-05 Review the completed checklist with leadership, IT, and authorized stakeholders. Review meeting notes Not Reviewed High
P-06 Prioritize critical gaps before the application or renewal deadline. Prioritized remediation plan Not Reviewed Critical
P-07 Confirm that supporting evidence is organized and accessible to authorized reviewers. Evidence package Not Reviewed High
P-08 Obtain final internal approval before submitting questionnaire responses. Final sign-off Not Reviewed Critical
P-09 Retain the final submission, supporting documents, and remediation plan for future renewals. Controlled archive Not Reviewed High
P-10 Schedule periodic follow-up reviews so readiness work continues after submission. Follow-up calendar Not Reviewed Medium

Tip: Treat unsupported questionnaire answers as risk items. Strong cyber insurance readiness usually requires technical evidence, documented ownership, and a plan for exceptions or remediation.

Industries we serve

Cyber insurance readiness support for organizations with real operational exposure.

Law Firms and Professional Services

Law firms, CPA firms, consultants, and professional services companies often need stronger evidence for email security, privileged access, data protection, and vendor risk. Start with law firm cybersecurity.

Real Estate and Financial Offices

Wire transfers, contracts, client records, email compromise, and vendor access make cyber insurance readiness especially important for transaction-heavy businesses.

Nonprofits and Local Organizations

Nonprofits often need practical evidence for cloud accounts, donor data, payment systems, staff training, and third-party services. Review nonprofit cybersecurity.

MSPs and Co-Managed IT

MSPs supporting clients with insurance questionnaires can use independent review to validate controls, clarify evidence, and prioritize remediation before submissions.

Ali Hassani, CISO and cybersecurity consultant
Led by Ali Hassani, CISO

Cyber insurance guidance that connects questionnaire answers to real technical evidence.

Ali Hassani brings 25+ years of cybersecurity, IT infrastructure, Microsoft 365, network security, firewall, backup, compliance, and executive risk experience to cyber insurance readiness reviews. The goal is to help business leaders and IT teams understand which answers can be supported, which controls need evidence, and which gaps need remediation before submission.

CISSPCCISOCCNPMCSEMCSA SecurityMCITP
From findings to implementation

When readiness gaps become IT projects, IT Perfection can help with the operational work.

OC Security Audit focuses on cybersecurity review, risk, evidence, and cyber insurance readiness. When the checklist identifies implementation needs, IT Perfection can support managed IT, Microsoft 365, endpoint, backup, network, monitoring, patching, and infrastructure projects when the readiness findings become practical implementation work.

Cyber insurance readiness for manufacturing and operational technology environments
FAQ

Questions about cyber insurance readiness

Does this checklist guarantee cyber insurance approval?

No. Underwriting decisions belong to the insurer. This checklist helps organize controls, evidence, ownership, and remediation priorities before application, renewal, or insurer follow-up.

Why do insurers ask for evidence?

Unsupported questionnaire answers can create risk for the business. Evidence such as screenshots, exports, policies, reports, and validation records helps show that security controls are actually in place.

Which controls are often most important?

MFA, privileged access, endpoint protection, backups, incident response, patching, vulnerability management, email security, firewall/VPN controls, and security awareness are frequently important in cyber insurance reviews.

Can OC Security Audit review our current questionnaire?

Yes. OC Security Audit can help review questionnaire responses, identify unsupported answers, organize evidence, and prioritize remediation before submission or renewal discussions.

Need help preparing for cyber insurance renewal?

Start with a focused readiness review and understand which controls, evidence, and remediation items should be addressed first.

Request a Readiness Review