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Ext. PublicationFrom Reactive to Resilient: What Cyber Insurance Trends Reveal About Cybersecurity Maturity
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Cyberattacks are still a growing reality for organizations across every industry. From ransomware shutting down operations to data breaches exposing sensitive information, companies of all sizes have become prime targets for cybercriminals. As threat and technology landscapes evolve, business leaders must view cybersecurity not just as a technical issue but as a strategic imperative.
A single incident can expose the fragility of an entire ecosystem. For example, a breach at a major third-party vendor could disrupt operations for hundreds of connected businesses, causing widespread delays and financial losses. Such events send a clear message to all industries: cyber resilience is no longer optional.
The Case for Resilience Over Reaction
Cyber resilience is more than just preventing attacks. It means ensuring business continuity, protecting customer trust and recovering quickly when disruptions occur. Yet, many organizations still operate with legacy systems, flat network architectures, backups that are also insecure and hard-to-patch technologies that make resilience difficult to achieve.
This is where cyber insurance enters the conversation as both a financial safety net and mirror, reflecting an organization’s cybersecurity posture. Increasingly, cyber insurance questionnaires are functioning as informal reviews, revealing whether companies are genuinely prepared for today’s threats.
What Cyber Insurance Is Telling Us
Over the past few years, cyber insurers have significantly tightened their underwriting standards. Organizations applying for coverage are now expected to demonstrate a baseline level of cybersecurity maturity. Common areas of scrutiny include:
- Multi-factor authentication (MFA) across all user accounts and critical systems
- Endpoint Detection and Response (EDR) solutions
- Regular backup and restore testing with immutable protection for storage
- Incident response planning and tabletop exercises
- Cloud security monitoring and baselines for configurations
- Third-party risk management and vendor assessments
These are no longer “nice to haves.” They’re prerequisites. Additionally, misrepresenting your security posture on an insurance application can lead to denied claims, rescinded coverage or costly disputes after an incident.
Multiple Data Sources
The data driving these expectations can be seen outside of the underwriter’s black box. Industry research, such as the 2025 Verizon Data Breach Investigations Report (DBIR), provides additional insights into the threats organizations face. The DBIR analyzed more than 22,000 security incidents across industries and offered a glimpse into the trends shaping insurance requirements, including previews of what may be coming next:
- Third-party risk remains a major vulnerability: Breaches in partner and supplier ecosystems are increasingly common, disrupting a wide range of organizations and underscoring the need for proactive planning around vendor security failures.
- Espionage is an emerging threat: Espionage-related breaches rose sharply from 1% to 16%, suggesting either a shift in attacker tactics or changes in data reporting. These actors are stealthier and harder to detect than traditional cybercriminals.
- Insider threats are declining but still present: While misuse of privileges has decreased, insider-related breaches often go undetected for long periods and can be difficult to uncover. Collusion between internal and external actors is rare but still a concern.
- Human error continues to drive breaches: Mistakes such as misconfigurations and accidental disclosures remain common. While eliminating them entirely is difficult, implementing controls to detect and respond quickly is essential to minimize damage.
Where Scrutiny Is Increasing: Beyond the Questionnaire
While cyber insurance questionnaires offer a standardized view of an organization’s general security posture, insurers are increasingly going beyond the checkbox, especially when evaluating complex operations or high-risk sectors.
Areas of higher scrutiny
Organizations can expect follow-up questions or deeper underwriting reviews in areas such as:
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- Third-party risk management: Insurers want to know how dependencies are assessed, monitored and segmented to prevent cascading failures. This includes outsourced service providers that may be performing a critical IT function.
- Hard-to-patch or other specialized systems: Certain technologies or operational equipment that cannot be easily patched, upgraded or replaced, often due to compatibility or operational constraints, may draw additional scrutiny.
- Incident response testing: It’s not just whether a plan exists, but how often the plan is tested, how robust the testing is and whether all key teams, from IT to leadership, are involved.
- Cloud and hybrid environments: Insurers ask for proof of the environment’s design, including safeguards via architectural diagrams and defined controls.
- Identity and access management (IAM): With the growing number and types of accounts across organizations, insurers are increasingly verifying that MFA and other controls are consistently applied across the whole of the environment, including the use of SaaS applications hosted by a third-party.
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Post incident scrutiny: Failed controls
There have also been cases where, following a breach, insurers have asked for evidence of controls that were represented to be in place on the original application. If those controls were misrepresented intentionally or not, it can lead to:
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- Coverage denial
- Policy rescission
- Litigation over misrepresentation
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This trend reinforces the need for cross-functional collaboration when completing insurance applications. Chief information security officers (CISOs), IT, compliance and legal teams should all be involved to ensure accuracy and defensibility.
Leadership Takeaways
For executive team members and business leaders, the message is clear: cyber insurance is no longer just a financial product — it’s a strategic signal. Cyber insurance questionnaires can be used as an indicator of current trends in the cyberspace, what minimum standards the market expects and how your organization’s security posture compares to peers.
To lead effectively in this environment, leaders should:
- Treat insurance applications as risk assessment exercises, not paperwork
- Involve CISOs (or equivalent), IT, compliance, legal and critical business unit leaders in the process
- Prepare supplemental documentation that defines existing compensating controls for those items that require an answer to the effect of “Yes, but …”
- Use insurer feedback, such as published trend reports and analyses, to help prioritize security investments and roadmap initiatives
From Compliance to Confidence
Businesses have long operated in a compliance-driven environment. However, in today’s threat landscape, compliance alone is not enough. Resilience is the new benchmark, and cyber insurance trends are helping to define what that looks like.
By paying attention to what insurers are (and what they’re not) asking about, leaders can gain valuable insights into their own maturity and take proactive steps toward a more secure, resilient future.
Are you ready to strengthen your organization’s resilience? Weaver’s cybersecurity consulting team can help you assess your current security posture and prepare for today’s evolving threats. Contact us today to start building confidence beyond compliance.
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