Insurers are asking questions most firms can't answer with confidence.
Cyber insurance renewal questionnaires have become dramatically more detailed since 2021. What was once a one-page form is now a 30–60 question technical assessment. Insurers are denying claims and voiding policies based on inaccurate responses — not just after breaches, but during routine audits.
The controls they're asking about — MFA on all remote access, endpoint detection and response, privileged access management, tested backups — are exactly what we implement and manage. We make sure your answers are accurate before you sign.
"Is multi-factor authentication enforced for all users accessing email remotely?"
Most firms: not enforced, just "encouraged"
"Do you have endpoint detection and response (EDR) deployed on all devices?"
Most firms: antivirus only, or partial deployment
"Are privileged/admin accounts separated from standard user accounts?"
Most firms: attorneys and admins use single accounts for everything
"Do you perform regular tested backups and have a documented recovery plan?"
Most firms: backups exist, but untested and undocumented
"Do you have a written incident response plan?"
Most firms: no
"Have you conducted a security awareness training program in the past 12 months?"
Most firms: no documented program
Sentinel Cyber Insurance Readiness Assessment.
Questionnaire simulation — we complete your current insurer's application form (or a standardized equivalent) against your actual environment, with honest current-state answers
Control gap report — every control the insurer asks about, rated pass/partial/fail, with the specific technical gap described in plain language
Premium impact analysis — we identify which gaps are most likely driving your current premium, based on known insurer weighting models
Remediation plan — ranked list of what to fix, estimated effort, and whether each item is in-scope for our managed services or requires separate engagement
Evidence package — documentation suitable for your broker or insurer demonstrating current control status and remediation commitment
60-minute debrief call — we walk your principals through the findings and discuss remediation options before your renewal date
| Control insurers require | Covered in |
|---|---|
| MFA on all remote access | Standard+ |
| Endpoint Detection & Response (EDR) | All tiers |
| 24/7 security monitoring | All tiers |
| Automated patching | All tiers |
| Privileged access management | Premium+ |
| Managed encryption enforcement (BitLocker + Intune) | Premium+ |
| Email security (phishing/sandbox) | Premium+ |
| Tested backup with documented RTO | Premium+ |
| Security awareness training | Compliance |
| Written incident response plan | Compliance |
| Dark web credential monitoring | Compliance |
| Annual security risk assessment | Compliance |
| Password manager / credential hygiene | Compliance |
| Third-party vendor security review | Compliance + vCISO |
Closing control gaps before renewal can improve underwriting outcomes, reduce questionnaire friction, and may help your broker secure better terms. We do not place policies and we do not guarantee premium reductions.
We've worked alongside these and similar insurers:
Coalition · Corvus · At-Bay · Chubb · Travelers · Hartford · Beazley · AXA XL
From inquiry to renewal-ready.
Discovery call (free)
We learn about your environment, your current insurer, and your renewal timeline. 15–20 minutes. No charge.
Technical review
We review your current IT environment — M365 configuration, endpoint posture, backup status, access controls — and map it against your insurer's questionnaire or a standardized framework. Typically requires 2–4 hours of access to your environment.
Report delivery (within 3 weeks)
Written gap report, questionnaire simulation, and evidence package delivered. Suitable for review by principals, legal counsel, and your broker.
Debrief call
60-minute walkthrough of findings. We answer questions, clarify technical gaps in plain language, and discuss remediation options and timeline.
Remediation (optional)
If you engage us for managed services, we implement the controls before your renewal date and produce updated evidence documentation for your broker. Most core controls can be implemented within 4–6 weeks of onboarding.
- — 90–120 days before your renewal date — enough time to close gaps before you sign
- — After a denial or significant premium increase — understand what drove it
- — When taking on new regulated clients who ask for evidence of your security controls
- — Pre-IPO or major transaction — insurance buyers will scrutinize your coverage and controls
Renewal coming up? Let's make sure you're ready.
Schedule a free 15-minute call. Tell us your renewal date and current insurer — we'll tell you honestly whether you have time to close the most critical gaps before you sign.
Free 15-Minute IT Consultation