Your renewal quote came back with a sharp premium hike, a shrinking coverage limit, or a flat decline. The underwriter is not being arbitrary. Carriers now treat penetration test reports and external attack surface scans as hard evidence of risk, and a single unresolved finding can move you from "preferred" to "uninsurable" in one review cycle.
Insurers have learned which technical weaknesses correlate with real claims: ransomware, business email compromise, and wire fraud. When a pentest report lands on an underwriter's desk, they are scanning for a specific set of controls and gaps. This guide walks through the 15 findings that carriers consistently flag, with the exact tooling a tester uses to surface each one, so you can remediate before the renewal conversation instead of after the denial.
Underwriters map pentest findings to loss scenarios. Missing multifactor authentication maps to credential theft and ransomware. Exposed remote desktop maps to initial access. End-of-life software maps to mass exploitation. The report is read as a predictive model, not a compliance checkbox.
The gap most organizations miss is that carriers increasingly run their own outside-in scans using data from internet-wide scanning platforms. If your external posture disagrees with your self-attestation questionnaire, the renewal stalls. A clean, independent assessment that matches your controls narrative is the fastest path to a favorable quote. If you want that narrative validated before submission, a scoped engagement with Redfox Cybersecurity can close the gap between what you claim and what an attacker sees.
This is the single most weighted control on nearly every carrier questionnaire. Underwriters want MFA on VPN, webmail, remote desktop gateways, and all administrative accounts. A tester confirms coverage by attempting authentication against exposed portals and checking whether a valid credential alone grants access.
A common validation against Microsoft 365 or on-prem services uses a password spray that deliberately avoids lockout thresholds:
netexec smb 10.10.0.0/24 -u users.txt -p 'Winter2026!' --continue-on-success
netexec ldap dc01.corp.local -u svc_backup -p 'Winter2026!' -M maq
[cta]
If any protocol accepts the credential without a second factor, the finding goes straight to the carrier's high-risk column. Legacy authentication endpoints that bypass conditional access are the usual culprits.
Open RDP is a top ransomware entry vector, and carriers treat any exposed 3389 as a near-automatic repricing trigger. The same applies to exposed SMB, WinRM, and database management ports.
Testers enumerate the external perimeter with fast, accurate scanning before probing service specifics:
nmap -Pn -sS -p 3389,445,5985,1433,3306 --open -iL scope.txt -oA perimeter
nmap -Pn -p 3389 --script rdp-ntlm-info 203.0.113.10
[cta]
If 3389 responds, the next question the underwriter asks is whether network level authentication is enforced and whether the gateway sits behind MFA. A bare, internet-facing RDP host is one of the clearest reasons a renewal gets declined.
Carriers subscribe to the same threat intel you do. A known, exploited CVE on your perimeter that matches a mass-exploitation campaign is a direct line to a claim. Underwriters specifically look for the vulnerabilities on the CISA Known Exploited Vulnerabilities list.
Modern external assessments use template-driven scanners that map directly to current exploitation activity:
subfinder -d targetcorp.com -silent | httpx -silent | \
nuclei -t http/cves/ -severity critical,high -rate-limit 20 -o nuclei-ext.txt
[cta]
The remediation standard insurers expect is a defined patch SLA: critical external issues closed within days, not quarters. A report showing stale, exploitable services tells the carrier your patch program does not function under pressure.
Unsupported operating systems, firewalls, and appliances cannot receive security patches, so any new vulnerability is permanent. Underwriters flag end-of-life Windows Server builds, legacy VPN concentrators, and out-of-support hypervisors.
Fingerprinting banners and versions during the engagement makes this visible:
nmap -Pn -sV --version-intensity 9 -p- 203.0.113.0/24 -oA versions
httpx -l hosts.txt -title -tech-detect -status-code
[cta]
A single out-of-support edge device, such as an unsupported SSL VPN, often carries more underwriting weight than a dozen medium-severity web findings, because these appliances are repeatedly targeted in real intrusions.
Ransomware operators rarely stop at one host. They abuse Active Directory to escalate and spread, so carriers increasingly ask about internal AD hardening. Kerberoasting and AS-REP roasting are the two findings testers surface most often, because both let an attacker crack service or user credentials offline.
netexec ldap dc01.corp.local -u analyst -p 'P@ss' --kerberoasting kerb.txt
netexec ldap dc01.corp.local -u analyst -p 'P@ss' --asreproast asrep.txt
hashcat -m 13100 kerb.txt rockyou.txt
[cta]
When service accounts use weak passwords and own privileged group membership, a tester can move from a standard user to domain dominance in under an hour. Mapping those paths visually with BloodHound shows the underwriter exactly how a breach would propagate, which is why internal AD review is central to Redfox Cybersecurity assessments.
A flat network means one compromised laptop can reach the finance server, backups, and domain controllers. Carriers now ask directly whether critical systems are segmented from general user space, because segmentation is the difference between a contained incident and an enterprise-wide ransomware event.
Testers validate segmentation by attempting reachability across VLAN boundaries from a foothold:
nmap -Pn -sn 10.50.10.0/24
netexec smb 10.50.10.0/24 --gen-relay-list targets.txt
[cta]
If a workstation subnet can freely reach server and backup subnets over SMB, RDP, and management ports, the report documents a lateral movement risk that underwriters price heavily.
Every extra domain admin is another target for credential theft. Underwriters want a tightly controlled count of privileged accounts, tiered administration, and no standing domain admin rights on everyday workstations.
Enumeration of privileged group membership is a quick tell:
netexec ldap dc01.corp.local -u analyst -p 'P@ss' --admin-count
netexec smb 10.10.0.0/24 -u analyst -p 'P@ss' --local-auth --loggedon-users
[cta]
Reports that reveal dozens of domain admins, shared local administrator passwords across hosts, or service accounts with unnecessary privilege confirm to the carrier that a single phishing success becomes a full compromise.
EDR has moved from a nice-to-have to a baseline underwriting requirement. Carriers want coverage across servers and workstations, with alerts going to a monitored queue. A pentest reveals gaps when payloads execute and tooling runs without detection or response.
During an engagement, testers note whether known offensive behavior triggers any alert at all. Hosts with no EDR agent, agents in audit-only mode, or large exclusion lists that neuter detection all become findings. An environment where a tester can dump credentials and move laterally in silence signals to the underwriter that a real intrusion would also go unnoticed until encryption begins.
Business email compromise and wire fraud drive a large share of cyber claims, so carriers inspect your email authentication posture. Missing or permissive SPF, DKIM, and DMARC records make spoofing trivial.
These records are checked directly from DNS:
dig +short TXT targetcorp.com | grep spf
dig +short TXT default._domainkey.targetcorp.com
dig +short TXT _dmarc.targetcorp.com
[cta]
A DMARC policy set to none, or absent entirely, tells both attacker and underwriter that inbound spoofing protection is weak. Carriers often ask specifically for an enforced DMARC policy of quarantine or reject as a condition of favorable terms.
Default logins on printers, cameras, management consoles, and network gear remain a reliable foothold. Reused passwords across accounts turn one leak into many compromises. Underwriters associate both directly with breach frequency.
Testers probe management interfaces and known default credential sets:
nuclei -l web-targets.txt -t http/default-logins/ -o defaults.txt
hydra -C defaults-list.txt -s 443 203.0.113.20 https-get /admin
[cta]
Finding a vendor default still active on an internet-facing device is an immediate credibility problem during renewal, because it suggests basic hardening steps were never completed.
An internet-reachable database or an open storage bucket is a data breach waiting to be indexed. Carriers that write privacy and breach-response coverage scrutinize exposed data stores closely.
Perimeter scans catch exposed database ports and unauthenticated services:
nmap -Pn -p 1433,3306,5432,6379,27017,9200 --open -iL scope.txt -oA db-exposure
nuclei -l hosts.txt -t http/exposures/ -severity high,critical
[cta]
An exposed Elasticsearch index, an open Redis instance, or a SQL port reachable from the internet signals that regulated data may already be accessible, which raises both the probability and the potential severity of a claim.
VPN concentrators and firewalls are the front door, and attackers hammer them with known exploits and credential attacks. Carriers want current firmware, enforced MFA, and strong TLS on these devices.
Testers inspect TLS configuration and portal behavior on perimeter appliances:
testssl.sh --severity HIGH https://vpn.targetcorp.com
nmap -Pn -p 443 --script ssl-enum-ciphers vpn.targetcorp.com
[cta]
Weak cipher suites, outdated firmware with public exploits, or a VPN login page that accepts single-factor credentials all become high-weight findings. Because edge devices are the most reliably exploited systems in modern intrusions, a review of your perimeter by Redfox Cybersecurity directly addresses what carriers check first.
Public web applications expand your attack surface and often hold or front sensitive data. Injection flaws, broken authentication, and insecure direct object references are the classes carriers care about, because they lead to data theft and account takeover.
Testers combine content discovery with targeted injection testing:
ffuf -w wordlist.txt -u https://app.targetcorp.com/FUZZ -mc 200,301,403
sqlmap -u "https://app.targetcorp.com/item?id=1" --batch --risk 2 --level 3
[cta]
An exploitable injection point or an authentication bypass on a customer-facing application tells the underwriter that an attacker can reach your data without ever touching the internal network.
Carriers are increasingly asking about dwell time, the gap between intrusion and detection. Without centralized logging and alerting, that gap stretches to months, which raises claim severity. During a test, the absence of any investigative response to noisy activity becomes a documented finding.
Reports note whether authentication failures, credential dumping, and lateral movement generated alerts, and whether logs from endpoints, servers, and perimeter devices feed a central platform with retention. An environment that cannot reconstruct an attacker's path after the fact tells the underwriter that a claim will be larger and harder to scope, which pushes premiums up or coverage down.
Backups decide whether a ransomware event is a bad week or a company-ending one, so carriers treat backup posture as a core underwriting control. They want immutable or offline copies, access separated from production credentials, and evidence that restores are tested.
Testers check whether backup infrastructure is reachable and whether the same domain credentials that run production also control backups:
netexec smb 10.60.10.0/24 -u analyst -p 'P@ss' --shares | grep -i backup
nmap -Pn -p 902,9392,9080 10.60.10.0/24 --open
[cta]
If a single compromised domain account can reach and delete backups, the recovery control the carrier is counting on does not exist. Immutable, segmented backups with independent credentials are frequently a condition of binding coverage.
Treat the underwriting questionnaire as a technical control audit, not a form. Each claimed control should be independently verifiable, because carriers validate against external scan data and, increasingly, against your submitted pentest report. The fastest denials come from mismatches between attestation and reality.
Work the findings in loss-driven order. Close MFA gaps and exposed remote access first, because those carry the heaviest weight and map to the most common claims. Remove end-of-life edge devices next, then harden Active Directory and segment critical systems from user space. Validate that backups are immutable and that detection actually fires on offensive activity.
Then commission an independent assessment that produces the same artifact the underwriter will read. A report from Redfox Cybersecurity that shows remediated findings, a working patch SLA, and tested recovery gives your broker concrete evidence to negotiate better terms rather than a questionnaire the carrier has to take on faith.
Cyber insurance underwriting has become a technical discipline, and your pentest report is now part of the pricing model. The 15 findings above are not an arbitrary list. They are the controls carriers have tied to real ransomware, business email compromise, and data breach claims, which is why each one can move a renewal from approved to denied.
The organizations that renew smoothly are the ones whose independent assessments confirm their control narrative: MFA everywhere it matters, a hardened perimeter, segmented networks, controlled privilege, enforced email authentication, working detection, and recoverable backups. Fix the heavy-weight items first, validate them with an assessment that mirrors what the underwriter will scrutinize, and walk into the renewal with evidence instead of promises. That shift, from self-attestation to proof, is what keeps your coverage in place and your premium under control.
Redfox Cyber Security Inc.
8 The Green, Ste. A,
Dover, Delaware 19901,
United States.
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