Cyber Insurance Readiness Assessment

See where you stand on the questions carriers actually ask — and what to do about each one.

A free Renewal Readiness Check for the owner or office manager whose cyber insurance renewal just asked for proof. It walks the controls carriers most often ask about — multi-factor sign-in, endpoint protection, tested backups, a written incident plan, and the practices around them — and shows where you stand on each, in plain English. With it comes a working toolkit: the renewal-form decoder, the evidence-pack checklist, the vendor worksheets, and the broker-call script. The check runs in your browser. Your answers never leave your device.

Free first

Two free ways to see if the toolkit fits.

1. Take the free Renewal Readiness Check

A short self-check across the controls cyber insurance carriers most often ask about — multi-factor sign-in, endpoint protection, tested backups, a written incident plan, and the supporting practices around them. A few minutes, in plain English. You get a green / amber / red read on each area and a clear next step for anything that isn't green yet. Runs in your browser. No email required; nothing is sent anywhere.

Take the free check →

2. Read the free guide

A plain-English walk through the renewal form: what each common question means, what carriers generally treat as "done," and what evidence is worth keeping — control by control, before you answer anything. Yours to keep.

Read the free guide →
Who this is for

This is for the renewal form — and for being ready if you ever claim.

It helps you prepare for a cyber insurance application or renewal: what each question means, what usually counts as a yes, and what evidence to keep so your answers hold up. We are not a broker, an agent, or an insurer, and nothing here is insurance or legal advice — your policy wording controls, and coverage questions belong with your broker or carrier. If the renewal has pointed you at deeper gaps — the controls themselves rather than the form — the SMB Security Assessment builds the baseline this check reads against.

If what you need is a general security baseline rather than renewal answers, the SMB Security Assessment covers the same core controls without the insurance lens. If something has already happened and you're deciding what to do right now, start with First 4 Hours.

Pick a tier

Three editions: one to finish this renewal, one to make staying covered routine, one for the advisor who runs renewals for clients.

Solo
$49one-time
For the owner or office manager with a renewal form on the desk, who needs to know what each question means and answer it honestly.
  • The Renewal-Form Decoder — every common question in plain English: what it means, what usually counts, and what proof looks like
  • The Evidence Pack Checklist — the per-control records worth keeping, dated and filed, so an answer is more than a memory
  • The Incident One-Pager — the first-calls page: who you'd call, in what order, and where it lives
  • The Stand-Up-The-Controls Guide — the controls insurers ask about, and how to actually put each one in place
  • The Email Security & Payment-Fraud Controls Quick-Start — the two controls behind most claims, stood up properly

Enough if you have one renewal in front of you and want to get through it honestly and well.

Buy Solo — $49
Pro Advisor
$199one-time
For the broker, managed service provider (MSP), or fractional IT lead running readiness across client renewals.
  • The Multi-Client Readiness Tracker — every client's controls, evidence, and renewal dates in one view
  • The Client-Deliverable Licence — use the worksheets and reports in your own client work
  • The Client Report Template — a clean readiness report you can put your name on
  • Everything in Solo and Team

Step up here if you answer for more than one business's renewal.

Buy Pro Advisor — $199

Every tier is a one-time purchase with a 30-day money-back guarantee, no questions asked, and free updates while the toolkit is in our catalogue.

How access works: the documents in every tier are downloads you keep, and the assessment app unlocks in your browser with the licence key from your purchase receipt — no account, no sign-in. The key activates on up to 3 devices on the solo tier, 7 on the middle tier, and 13 on the top tier.

From Sylvan Press

The companion book: the plain-English guide behind this toolkit.

The book teaches the judgement; the toolkit does the work with you. Cyber Insurance in Plain English walks a small business from "the renewal asked for proof" to covered, current, and ready to claim.

Plain-English readiness tools that never see your answers.

The free Renewal Readiness Check scores you in the browser. We do not collect your answers, your results, or anything about your policy. We collect your email address only if you choose to enter it for the free guide. Nothing else.

Our website uses Cloudflare's server-side traffic counts for page totals — no scripts added to the page, no cookies, no data that identifies you.

From the blog

The situation this toolkit is built for, written up.

Your first cyber insurance renewal questionnaire — ~7 min read.