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In a first-person account on DEV Community, IT professional Serguey Shinder describes a cyber-insurance renewal questionnaire that ended up setting the order of his company’s security work. His account raises a useful question for any organization approaching renewal: how do you meet an insurer’s requirements without letting them replace your own assessment of business risk?
What happened during the renewal
Shinder says the company’s renewal questionnaire had expanded from a one-page form with 12 questions three years earlier to 140 questions across nine sections. Six sections, he reports, required documentary evidence, and a quotation was conditional on the insurer scanning the company’s internet-facing assets. He does not name the insurer or publish the questionnaire, so these figures describe his experience rather than a verified or typical underwriting process. (DEV Community)
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His team spent 11 working days answering the form. In doing so, he says, it found gaps in remote-access multifactor authentication (MFA), separation of privileged and everyday accounts, offline or immutable backups, and endpoint detection on servers. The account identifies specific exceptions: a supplier’s legacy connection, 41 staff outside the stated MFA coverage, only one of three backup copies offline or immutable, and six older servers without the endpoint agent.
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Which controls the questionnaire brought into focus
- Remote-access MFA: The company found that the stated MFA coverage did not include 41 staff. MFA adds an authentication step beyond a password; the relevant task in this account was closing the coverage gap for remote access.
- Separate privileged accounts: Shinder describes separating accounts used for administrative privileges from those used for everyday work, reducing the overlap between routine activity and powerful access.
- Offline or immutable backups: The company had one such copy among three backup copies, according to Shinder. He reports moving another copy offline.
- Endpoint detection on servers: Six older servers lacked the endpoint agent. Shinder says those servers were replaced as part of remediation.
The account does not identify the insurer’s exact control definitions or evidence standards. An organization should therefore work from the wording of its own questionnaire and policy documents rather than assume these examples map precisely to another insurer’s requirements.
#1 Best Overall
How the company responded
Shinder says the findings led to 14 weeks of remediation. The reported changes were retiring the supplier’s legacy connection, replacing the six older servers, moving another backup copy offline, and separating privileged accounts. This is a chronology from one account, not a recommended deadline or proof that every organization should remediate controls in the same order.
The useful operational lesson is to treat each answer as something that needs an accountable owner and evidence, not simply a checkbox. Shinder says the team now attaches evidence to each question and has the declaration signed by someone who can be shown proof. In his words: “Every question now has a named owner and evidence attached, and the declaration is signed by someone who can be shown proof.”
Should insurer requirements set security priorities?
Shinder’s answer is effectively no: insurer requirements should be tracked, but they should not displace the organization’s own risk register. He argues that the questionnaire drove a remediation order he had not chosen, while leaving out risks he considered operationally serious, including depot control systems, reliance on a single logistics platform, and the possibility that a supplier could be unavailable for two weeks.
That is his critique of his experience, not evidence that insurers generally overlook those risks or that underwriting questions universally reflect claims data in a particular way. The practical distinction is between what renewal asks you to evidence and what could materially disrupt your organization. A control can matter to both, but the lists are not automatically identical.
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- Keep insurer-requested controls visible, with an owner, evidence, and any stated renewal deadline.
- Maintain a separate view of business-specific dependencies and failure scenarios, such as critical facilities, platforms, or suppliers.
- Review both lists together when deciding remediation order, so an underwriting deadline is considered without silently becoming the only measure of risk.
What the reported renewal terms do—and do not—show
Shinder reports that the premium increase was “not quite half,” the excess doubled, one category received a sub-limit, and the policy included two conditions precedent. He describes a condition precedent as a clause that can make cover void for an event if the named control was absent when that event happened. The article supplies no policy wording, insurer identity, or governing law; the legal effect of such a clause depends on the actual contract and applicable law. This account is not a basis for interpreting a particular policy.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.What to take from one company’s story
The account is useful as a governance example, not a benchmark for questionnaire length, insurer practice, remediation timing, or renewal pricing. Shinder reports that a detailed renewal exercise exposed control gaps and prompted specific changes. He also argues that an insurer’s checklist did not capture every operational risk his organization cared about. Keeping evidence-backed underwriting requirements alongside a business-specific risk register addresses both concerns without treating either list as complete on its own.
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Read Serguey Shinder’s account on DEV Community.
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