WorkflowSpecialty, E&S & London Market

Cyber Underwriting Risk Assessment

Cyber underwriting risk assessment that finds the contradicted answer before the quote

Control gaps found before the quote, each linked to the answer or scan.

See one case, screen by screen ↓
demo212answersread from five documents, with 20 scan and pen-test findings matched to them
demo3signed answers contradicted by the evidence on file — each one a pre-bind subjectivity
target25minfrom documents to a graded scorecard
target15controls graded the same way, both sides cited
In short

What is Cyber Underwriting Risk Assessment?

Software that reads a cyber submission — the application, ransomware supplement, outside-in scan, pen test and loss history — and grades each security control against the carrier’s minimum-controls guide. Cyber Underwriting Risk Assessment puts every signed answer beside the evidence for it, flags the contradictions and writes the subjectivities before the quote.

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Updated

The problem

Why the contradicted answer is found after the loss, not before the quote

A cyber submission is four or five documents talking about the same dozen controls: the application, the ransomware supplement, the outside-in scan you ordered, sometimes a penetration test summary, and the loss history. They often disagree. The application says MFA covers all remote access; the scan finds remote desktop open to the internet with no MFA gateway in front of it.

Today the underwriter reads every one of them end to end to find that line — three to four hours on a mid-market account. Subjectivities get written from memory, so the wording changes from one underwriter to the next. And a contradiction nobody caught becomes the coverage dispute after a ransomware event: in Travelers v. International Control Services (2022) the signed application said MFA was in place, forensics after a ransomware attack found it was not, and the carrier sued to rescind; the parties agreed the policy was void from the start.

estimated3–4hof reading per mid-market submission, by hand
typical60%of claims in Coalition’s 2025 report began with business email compromise or funds transfer fraud
Where a submission’s hours goestimated
By hand3.8 days
With the solution0.7 days
  • Reading the application and ransomware supplement1.3 → 0.1 d
  • Reading the outside-in scan and pen test0.8 → 0.1 d
  • Putting answers beside evidence, control by control0.8 → 0.1 d
  • Writing subjectivities and the broker letter0.5 → 0.1 d
  • The underwriting note for the file0.5 → 0.1 d

Estimated split, in hours, for one mid-market cyber submission, by hand and with the solution.

How it works

How a submission moves

Five specialist agents put every signed answer beside the scan and pen test; the cyber underwriter decides and sends.

What comes in
Submission in5 documents · application, supplement, scan, pen test, losses
Agents at work
Submission readerevery answer cited
Then
Scan matcher
Then
Control grader15 controls
Then
Subjectivity writer
Underwriting note writer
A person decides
Cyber underwriterdecides and sends
What comes out
Graded scorecard
Subjectivities
Quote and note
One case, step by step

One submission, from five documents to a signed note

Lattimer Freight Systems, a freight and warehousing company in Columbus, Ohio, wants a $5,000,000 limit. Its wholesale broker sent five documents. Here is what happens next, screen by screen, in the working solution.

  1. 01Monday morning

    The whole risk, control by control, on one screen

    Nadia Okafor · Senior cyber underwriter

    Nadia opens Lattimer Freight: revenue $186.4m, 640 employees, 14 terminals, $5,000,000 excess of a $250,000 retention, effective 1 Nov 2026, quote due Friday. The grade strip already reads 3 contradicted, 1 partial, 3 gap, 1 ask the broker, 1 watch and 6 meets. The control score is 58 out of 100 — below the appetite floor of 60.

    “Below the floor of 60 · 78 once S1–S3 are met”

  2. 02On arrival

    Every submission read the day it lands

    Ravi Menon · Underwriting assistant

    The queue ranks 11 cyber submissions by the date the broker needs the quote, with the documents each one carries: application, supplement, scan, pen test, loss history. Six have a contradicted answer and seven quotes are due by Friday. Brindlewood County Schools is waiting on the broker for its ransomware supplement; Ostrander Cold Storage has its scan still running.

  3. 03Read

    Every answer, with its question number and page

    Submission reader

    The application is 14 pages, signed 18 Sep 2026 by Martin Greaves, CFO. Each answer the scorecard uses carries a mark in the margin, coloured by its grade — Q22 on remote access MFA and Q31 on critical patching are marked contradicted. A blank stays “not answered”; nothing is inferred.

    Limit: never infers an answer that was not given.

  4. 04Matched

    The outside-in scan, read finding by finding

    Scan matcher

    The scan ran on 9 Oct 2026: 37 internet-facing assets, 11 findings, mapped to 5 controls. SC-01 is the edge VPN appliance on firmware 7.0.12, on the known-exploited list since 21 Aug 2026. SC-03 is remote desktop open on 203.0.113.47 with no MFA gateway, first seen 2 Aug 2026.

    The scan is read, never run — the agents do not probe the insured’s systems.

  5. 05Run the check

    The signed answer first, then the evidence

    Control grader

    “Run the check again” replays the grading in view. The claims fill in first. On MFA on remote access the drawer slides open with the signed answer highlighted on the application page — Q22, “Yes” ticked, signed 18 Sep 2026 — while the grader matches the evidence.

  6. 06Seconds later

    The row flips to Contradicted

    Control grader

    The scan finding slides in as the scanner recorded it: 203.0.113.47:3389/tcp open, remote desktop, CN=LFS-TS01, login page with no MFA gateway. The sign turns to ≠ and the grade to Contradicted. Under “Why this grade”: the remote desktop login has been open for at least 68 days, and remote desktop with stolen passwords is the most common way ransomware gets in.

    “The evidence contradicts the signed answer.”

  7. 07Graded

    Each contradiction becomes a subjectivity from the library

    Subjectivity writer

    Three pre-bind subjectivities, three conditions after binding and one question to the broker, each worded from library v14 and citing both sides. DMARC at p=none becomes condition C2 within 60 days; 214 warehouse scanners on the office network become C3 within 90 days; 23 leaked credentials with no admin account stay on watch. The run log shows each step and its time.

    Limit: never invents wording outside the library, never relaxes a condition.

  8. 08Quote

    Terms and subjectivities, hers to edit

    Nadia Okafor · Senior cyber underwriter

    The indicated terms on the Corvane Specialty form: $142,800 annual premium against $96,400 expiring, a $250,000 social engineering sublimit, a 10-hour waiting period. If S1 is not met at binding, ransomware cover is sublimited to $2,500,000 at 50% coinsurance. Nadia can edit any wording or move an item between pre-bind and post-bind.

    “Nothing reaches Delia Ashcombe until you send it.”

  9. 09Sent · signed

    The quote goes to the broker; the note goes on file

    Nadia Okafor · Senior cyber underwriter

    Nadia sends the quote with three pre-bind subjectivities to Delia Ashcombe at Wexmoor & Pike. The underwriting note is already drafted — the risk, every grade with its evidence, and the basis for quoting below the floor. Score 58 is above the referral line of 50, the limit is within her authority and no contradiction was overridden, so no referral is needed. She signs.

  10. 10Every quarter

    What applications get wrong, across the book

    Celeste Imbert · Head of cyber

    418 submissions graded in Jul–Sep 2026: 146 contradictions in 97 of them, each turned into a subjectivity before the quote. MFA on remote access is contradicted in 31% of transport and logistics submissions. Of 212 conditions on bound policies, 13 are overdue — one click reminds the brokers.

Who it’s for

Built for everyone who touches a cyber submission.

The same submission, seen by the five people who carry it — in their own words, and what their week looks like now.

NO
Nadia OkaforSenior cyber underwriter, mid-market · authority to $5m
Underwriter
Before
“The application says yes to everything. The scan is where I find out.” Three to four hours of reading per submission.
Now
Starts from a graded scorecard with both sides cited, decides the three contradictions, and sends.
RM
Ravi MenonUnderwriting assistant
Underwriting assistant
Before
“Half my week is asking brokers for the page that’s missing.”
Now
Sees which submissions lack a supplement or scan the day they arrive, with the request already made.
GT
Graham TellerCyber risk engineer
Risk engineer
Before
“I see the open port; nobody tells me what the client signed.”
Now
Every scan and pen-test finding sits beside the signed answer it bears on.
CI
Celeste ImbertHead of cyber · owns the minimum-controls guide
Head of cyber
Before
“When we pay a ransomware claim, I want to know if we saw it coming.”
Now
Owns the guide and the subjectivity library as versioned rules, and sees what applications get wrong by control and industry.
DA
Delia AshcombeWholesale broker, Wexmoor & Pike
Broker
Before
“Tell me exactly what you need and I’ll get it signed.”
Now
Gets one letter: each subjectivity in the carrier’s wording, with the asset, the account and the due date.
Built on the engine

5 agents. Each with one job, and hard limits.

Five specialist agents put every signed answer beside the scan and pen test; the cyber underwriter decides and sends.

Submission reader

Reads the application, ransomware supplement, pen test and loss history; extracts every answer with its question number, page and signer, and counts such as devices with EDR as numbers.

  • Never infers an answer that was not given — a blank is “not answered”
  • Cites question and page for every value
Scan matcher

Reads the outside-in scan the carrier commissions and maps each finding — open ports, firmware, email records, leaked credentials, banners — to a control. Reads the pen-test findings the same way.

  • Never probes the insured’s systems itself
  • Reports only what the scan recorded
Control grader

Puts each signed answer beside the evidence against the minimum-controls guide and grades it: meets, partial, gap, contradicted, ask or watch.

  • Never grades a row without citing both sides
  • Never decides appetite
Subjectivity writer

Turns each contradiction into a pre-bind subjectivity, each gap into a condition with its due days, and each “ask” into a question to the broker — from the approved library, with the assets and accounts filled in.

  • Never invents wording outside the library
  • Never quotes, binds or relaxes a condition
Underwriting note writer

Drafts the note for the file and the letter to the broker, every statement cited.

  • Never sends anything — a person sends
Cyber underwriter

Decides each contradiction; head of cyber on referral. The agents propose; a named person decides.

Ask in plain words

Ask about any control, in plain words

Ask about any control, answer, finding or subjectivity — or tell it what to add. Every answer points to the page or finding behind it.

Why is MFA on remote access contradicted?

Because the signed answers and the scan disagree. Application Q22 and supplement Q4.2 both say yes: MFA on all remote access, including remote desktop. The scan of 9 October reached a remote desktop login at 203.0.113.47:3389 (LFS-TS01) with no MFA gateway in front of it, first seen 2 August. That made it S1, a pre-bind subjectivity with a rescan.

Which subjectivities must be met before binding?

Three, each with a rescan or written proof: S1, MFA on remote access (outside-in scan SC-03); S2, MFA on privileged accounts (pen test PT-4); S3, critical patching (outside-in scan SC-01). If S1 is not met at binding, ransomware cover is sublimited to $2,500,000 at 50% coinsurance.

Has Lattimer had a claim that points to these gaps?

One: LF-24-031, March 2024 — a spoofed carrier invoice, $84,300 paid. They adopted call-back verification on 30 April 2024, and the supplement confirms it for changes over $10,000. What is still open is the email side: DMARC is at p=none, so anyone can still send mail as the company. That is condition C2, due 60 days after binding.

Add EDR to 98% as a condition within 60 days

Added as C4. The application says EDR covers all endpoints and servers, but the supplement counts 612 of 651 devices with the agent — 94%, with 39 terminal servers missing it. The wording is library L-EP-02, due 60 days after binding. The quote and the letter to the broker now carry it.

Every screen

The working solution, as it ships.

12 screens from the working solution, on its sample data. Pick one to see it large.

The scorecardFifteen controls in three lanes — what they told us, what we found, the grade — with the score and the subjectivities as they are written.
Cyber submissionsEvery new and renewal submission, ranked by quote due date, with the documents present, contradictions and score.
The applicationEvery answer the scorecard used carries a margin mark coloured by its grade; click it to open the row.
The outside-in scan37 assets and 11 findings as the scanner recorded them, each mapped to the control it bears on.
The check, in viewThe signed answer comes up first, highlighted on its page, while the evidence is matched.
The evidence drawerThe scan finding beside the signed answer, why the grade is Contradicted, and the proposed pre-bind subjectivity.
The check, step by stepExposure, email and payments graded, and the run log: each agent’s step, what it found and how long it took.
Quote and subjectivitiesTerms, the ransomware sublimit option, every subjectivity with its library reference and sources, and the letter to the broker.
The underwriting noteThe risk, the grades with their evidence, the referral check and the record — ready to sign and file.
What applications get wrongContradictions by control and industry across the quarter’s 418 submissions, and conditions still open after binding.
The minimum-controls guideWhat is eligibility, required or priced by revenue band, and the ten approved subjectivity wordings.
SettingsDocuments read, grade rules, the score floor, referral rules and people — versioned and on the record.
Governance

Built for underwriting authority: cited, decided, on the record.

Every grade cites both sidesThe question number and page of the signed answer, and the scan or pen-test finding with its date. Click either to open the page or finding it came from.
The underwriter decidesAgents grade and draft. Keeping, asking about or overriding a contradiction is the underwriter’s call, and it is on the record.
Overrides go to referralOverriding a contradiction needs a reason and refers the file to the head of cyber — as do a score under 50 and a limit over $5m.
Wording only from the approved librarySubjectivities and conditions come from the library the head of cyber owns. Every change to the guide or library is a new version and re-grades open submissions.
The scan is read, never runThe agents read the scan the carrier ordered and the pen test the broker sent. They do not probe the insured’s systems, and a rescan before binding confirms the fix where the scan was the evidence.
Nothing goes out unless a person sends itAgents never quote, bind, decline or contact the insured. The letter reaches the broker when the underwriter presses Send, and the signed note is filed with the scorecard and the evidence.
Configuration

Your guide and your authority, not ours

What every submission is read against, how grades are set and who decides are settings — versioned and on the record.

SettingDefaultChoose from
Documents readApplication, ransomware supplement, outside-in scan, pen test, loss historyEach on or off
Ransomware supplementRequired for revenue over $25mRequested from the broker when missing
Partial grade for EDR coverage under98%Step up or down by 1%
Scan older than30 daysRescan before grading
Control score floor60Step up or down by 5 · below it, the quote needs a reason on the file
Refer to the head of cyberScore under 50, limit over $5m, or an overridden contradictionCeleste Imbert
Conditions after binding30 · 60 · 90 daysDefault due days
Overriding a contradictionUnderwriter, with a reasonGoes to referral
Connections

Works with the submissions you already receive

Cyber application and ransomware supplementevery answer, its question number, page and signer
Outside-in scan providerordered on arrival; ports, firmware, email records, leaked credentials
Penetration test or security assessmentfindings with their dates, when the broker sends one
Loss history and incident disclosuresfive years, each claim tied to the control it points to
Minimum-controls guide and subjectivity libraryrules by revenue band and the approved wordings
Broker correspondencethe quote letter with its subjectivities, sent by the underwriter
What it changes

The difference, in numbers.

Every figure is labelled: a target the solution is built to, an estimate, a typical published result, or a proven one.

target
25min
from documents to a graded scorecard
By hand3–4 h
With agents≈ 25 min
target
15
controls graded the same way, both sides cited
Every control
answer beside evidence
typical
60%
of cyber claims start with email compromise or payment fraud
Email and payments
read first on every submission

“demo” = seen in the working solution, on its sample submission · “target” = the design goal, measured in the live solution · “estimated” = our estimate (3–4 h by hand and the hours split) · “typical” = published figures (Coalition, 2025 Cyber Claims Report — 60% of claims began with business email compromise or funds transfer fraud). The Travelers v. International Control Services case is as reported by Reed Smith (2022). People, insureds, brokers and carriers named on this page are fictional — characters and sample data in the working solution.

Questions

What cyber underwriters ask us.

What is cyber underwriting risk assessment software?

Software that reads a cyber submission — the application, ransomware supplement, outside-in scan, pen test and loss history — and grades each security control against the carrier’s minimum-controls guide. Cyber Underwriting Risk Assessment puts every signed answer beside the evidence for it, flags the contradictions and writes the subjectivities before the quote.

How does it find a contradicted answer?

The submission reader extracts each answer with its question number and page; the scan matcher maps each scan and pen-test finding to a control. The control grader then puts the two side by side. When the evidence shows a signed yes is untrue — remote desktop open with no MFA gateway after the application said MFA covers all remote access — the row is graded Contradicted.

Which controls does it grade?

Fifteen, in six groups: identity and access (MFA on remote access, email and privileged accounts, separate admin accounts), endpoint (EDR, critical patching, unsupported systems), recovery (immutable tested backups, MFA on the backup console, incident response plan), exposure (network segmentation, leaked credentials), email and payments (email authentication, payment verification) and governance (phishing training).

Does it scan the insured’s network?

No. It reads the outside-in scan the carrier ordered and the pen test the broker sent, and reports only what they recorded. Where the scan was the evidence, a rescan before binding confirms the fix.

Where does the subjectivity wording come from?

Only from the approved library the head of cyber owns — for example L-RA-02 for exposed remote desktop or L-EM-01 for DMARC to p=quarantine. The writer fills in the assets and accounts from the evidence and cites both sides. Every library change is a new version.

Do underwriters stay in control?

Yes. The agents never quote, bind, decline, relax a condition or contact the insured. The underwriter decides each contradiction — keep, ask the broker or override with a reason — edits the wording, sends the quote and signs the note. An override refers the file to the head of cyber.

Can we use our own minimum-controls guide and referral rules?

Yes. Rules by revenue band, the EDR coverage threshold for a partial grade, how old a scan may be, the control score floor, referral triggers and the default due days for conditions are all settings.

How long does it take to go live?

The Agentic Solution Engine builds and deploys it from your requirements — your application and supplement forms, minimum-controls guide, subjectivity library and a sample of past submissions — and it goes live once every quality gate has passed. We will walk you through it on your own submissions first.

See it on
your submissions.

We’ll run Cyber Underwriting Risk Assessment on a sample of your own cyber submissions.