Cyber Insurance Readiness

Many firms discover during renewal that their documented controls don't fully match what the insurer is asking for. We close the gap between what your insurer requires and what you actually have.

The Problem

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.

Common questionnaire questions — and where firms struggle:

"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

The Assessment

Sentinel Cyber Insurance Readiness Assessment.

^$1,495

Flat fee · 2–3 week turnaround

What's included:

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

Assessment fee credited toward the first 3 months of Sentinel Workstation Package — Premium or Compliance if you proceed with managed services within 90 days.

Request an Assessment

How our managed plans address insurer requirements

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 policy + Intune key escrow)	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

Works with your existing broker

We're not an insurance broker and we don't sell policies. Our job is to make your IT controls accurate so your broker can place the best policy at the right premium — and so you can answer the questionnaire without guessing.

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

How It Works

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.

When to do this

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90–120 days before your renewal date — enough time to close gaps before you sign

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After a denial or significant premium increase — understand what drove it

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When taking on new regulated clients who ask for evidence of your security controls

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Pre-IPO or major transaction — insurance buyers will scrutinize your coverage and controls

We carry professional liability (E&O) and cyber liability insurance ourselves — and we're happy to provide certificates of insurance during your own vendor due diligence process. Certificates available on request at Compliance@SentinelSouth.com.

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.

Schedule a Free Call