Cyber Insurance Questionnaires

Cyber Insurance Questionnaires is a skill for Claude Code from WYRE-AI/msp-claude-plugins. It costs 92 tokens per session (1,487 once invoked), scanned A, original, Apache-2.0.

A skill for drafting cyber-insurance questionnaire answers with evidence from connected systems. These questionnaires ask about controls such as multi-factor authentication, endpoint detection, backups, incident response, and security training.

In plain words
What is it for?
Use it to prepare insurance renewal or application responses, check MFA and endpoint-security coverage, review backup and response evidence, and flag missing proof.
Why use it?
It replaces broad assurances with answers tied to current records and clearly identifies controls that cannot be verified.

Skill for Claude Code

Written for Claude Code: when-to-use in frontmatter.

Part of the compliance-pack plugin — 3 skills, 3 commands, 3 agents shipped together

Good fit Use it to prepare insurance renewal or application responses, check MFA and endpoint-security coverage, review backup and response evidence, and flag missing proof.

Compare 6 skills from other repositories ↓
Install with agentmods
npx agentmods add skills/wyre-ai/msp-claude-plugins/insurance-questionnaires
Install

Getting it into your agent

One page per mod, every tool's command on it. A separate URL per tool would split the same page into five that compete with each other.

Any agent
npx skills add WYRE-AI/msp-claude-plugins --skill insurance-questionnaires
Clone the repo
git clone --depth 1 https://github.com/WYRE-AI/msp-claude-plugins

Made for: Claude Code.

Or install compliance-pack, the plugin that ships this one along with the rest of its 3 skills, 3 commands, 3 agents.

Wrote this? Show the measurements

A badge with what this costs and how it scanned, read live from this page, so it follows the numbers instead of freezing them. Markdown for a README, HTML for a documentation site or a project page.

agentmods badge for Cyber Insurance Questionnaires

README.md
[![agentmods](https://agentmods.dev/badge/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires/github.svg)](https://agentmods.dev/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires)
Your own site
<a href="https://agentmods.dev/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires"><img src="https://agentmods.dev/badge/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires/github.svg" alt="Measured on agentmods" height="20"></a>

Or the 80×15 button, for a site that already has a row of RSS and ATOM ones. Only the verdict fits; the numbers stay here.

agentmods 80×15 button for Cyber Insurance Questionnaires

Your own site · 80×15
<a href="https://agentmods.dev/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires"><img src="https://agentmods.dev/badge/skills/wyre-ai/msp-claude-plugins/insurance-questionnaires.svg" alt="Reviewed on agentmods" width="80" height="20"></a>
Per session 92 Skills are progressive disclosure: only the name and description are preloaded; the body loads when the skill is used.
When invoked 1,487 The whole file, excluding the scripts and references it only reads on demand.
Security scan A 0 findings. A grade says what 26 rules found in the file — not that it is safe. Third-party audits
  • NVIDIA SkillSpector pass 7 Sept 2026
How audits are shown
Origin original No closer match found in the catalogue.
Token cost

What it costs to keep this loaded

Counted locally with the o200k_base tokenizer, which is exact for GPT models; Claude uses its own tokenizer and its counts differ. Treat this as one consistent yardstick across the catalogue rather than a bill. Prices are per million input tokens.

ModelPer sessionOnce invoked
Fable 5.1 $0.00092 $0.01487
Opus 5 $0.00046 $0.00744
Sonnet 5 $0.00018 $0.00297
Haiku 4.5 $0.00009 $0.00149

Measured 8d ago against content hash 506ee14ba554, method: parsed. Prices are Anthropic first-party input rates as of 2026-09-12, from the pricing page.

Security

Grade A, and why

Cyber Insurance Questionnaires scanned grade A with 0 findings against 26 rules in 11 categories — prompt injection, anti-refusal, data exfiltration, privilege escalation, supply chain, agent snooping, system-prompt leakage, SSRF and excessive agency — measured 8d ago.

A static scan of the body, not an audit. Every finding is printed with the line that produced it so you can judge whether it matters here. A mod is markdown that instructs an agent; that is exactly why what it instructs is worth reading.

Nothing flagged

None of the 26 patterns this scan looks for appear in this file: no shell pipes, no recursive deletes, no credential paths, no hidden text, no instruction-override or anti-refusal phrasing, no agent-config snooping. That is not a guarantee, it is the absence of the things that are checkable.

msp-claude-plugins/compliance-pack/skills/insurance-questionnaires/SKILL.md · 64 lines

How it starts

The opening of the file, as written. The whole thing — 64 lines — stays where its author put it; the contents beside it link to each section on GitHub.

Cyber Insurance Questionnaires

Overview

Cyber-insurance underwriters ask a fairly repetitive set of questions across carriers, because the same handful of controls (MFA, EDR, backup integrity, incident response readiness, security awareness training) drive the overwhelming majority of claims. The recurring failure mode in how these get answered is not malice — it's that whoever fills out the form is often answering from general impression ("yeah, we've got MFA everywhere") rather than a live query, and a policy gets bound or renewed on an answer that turns out to be wrong when a claim is filed. A wrong answer on a bound policy can be grounds for denial of a claim. This skill exists to replace impression-based answers with tool-verified ones, and to make "we can't verify this" a normal, expected answer rather than something to paper over.

The Standard Question Set and How to Answer Each

"Is multi-factor authentication enforced for all users, including privileged/admin accounts?"

Pull cipp__list_mfa_users for per-user registration/enforcement state and cipp__list_conditional_access_policies for policy-level enforcement (conditional access scoped to "All users" is a stronger answer than per-user MFA alone — say which mechanism is in place). Cross-check privileged accounts specifically via cipp__list_gdap_roles / admin role assignments — underwriters increasingly ask about admin/privileged accounts as a distinct sub-question. Answer with the actual coverage percentage and any known exceptions (service accounts, break-glass accounts), not a flat yes/no.

"Is Endpoint Detection and Response (EDR) deployed across all endpoints?"

Pull agent/device counts from whichever EDR/MDR connector is present (Huntress, SentinelOne, RocketCyber, or similar — check via conduit__search_tools). Compare deployment count against the client's known device inventory (RMM device count, or Liongard liongard__inventory_devices if RMM isn't connected) to state coverage as a fraction, not just "yes, deployed." A vendor being "connected" is not the same as 100% of endpoints having an active agent — report the actual ratio.

Read the full file on GitHub · 64 lines

Changes

What this file has done since we first saw it

Hashed on every crawl. A supply-chain change to an agent config is a question of when, not whether, so the history is kept rather than the latest state alone.

  1. 8d ago First seen · 64 lines · 92 tokens per session scan A 506ee14ba554

Subscribe to this mod's changes

Cyber Insurance Questionnaires is a skill published in the GitHub repository WYRE-AI/msp-claude-plugins (45 stars, last pushed 9d ago), licensed Apache-2.0. It adds 92 tokens to every session and 1,487 once invoked, about $0.0005 per session on Opus 5. A static security scan graded it A with 0 findings. No closer match exists in the catalogue, so it is treated as the original; first seen 2026-09-04.

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