Demystifying Questions Cyber Insurance Companies Will Ask You

by | Jul/8/2024

If you have existing or are applying for new Cyber Insurance coverage, be prepared for the questionnaire. Knowing what they’ll ask can give you time to implement systems to answer “yes” to the questions affecting your premium rates and whether you’re still considered insurable.

Common questions on insurance applications include:

Do you use MFA? Multi-factor authentication means users must go through a second step when logging in. A prevalent method for the second factor is using an authentication application on users’ phones. It is essential to use a number-matching requirement so that a user must type in a code displayed on their phone into their computer before authentication. Another second factor is time-based one-time password (TOTP) apps on phones that display a number on the phone that the user enters as part of the authentication process. The number displayed in the app resets periodically, typically every 30 seconds. Other factors include using hardware keys that plug into USB ports and biometrics, including fingerprints or facial recognition. A typical second factor is receiving an SMS text message with a code, but that method is vulnerable to attacks such as SIM Swapping. In the interest of security, you should enforce MFA everywhere possible, including VPN, Remote Desktop, and SaaS offerings.

Do you provide ongoing cybersecurity awareness training and periodic phishing simulation emails to measure worker proficiency? Your users must receive regular security awareness training, such as once per month and perhaps a comprehensive webinar or other presentation once a year. Additionally, services can send users a fraudulent or email phishing message once a month to measure their response, such as if they open the message, click on the simulated fraudulent link, and are duped into entering credentials. One often overlooked aspect of training and simulated phishing is that it might take time for your already overworked staff to configure, send, monitor, and produce reports about the results every month. You’re welcome to contact us to provide that service, and we do 100% of the work, so there is no additional burden on your workers. Training for new employees is available. We also provide comprehensive yearly training webinars and other presentations. Whatever training you use, be sure that it adapts to keep your users current with the rapidly evolving threat landscape.

Do you provide password management tools to users? Tools that remember and automatically enter users’ passwords can help encourage users to use different passwords for every login. Users with the habit of reusing passwords pose a risk to your organization. Once attackers compromise a password, they will attempt to use that same password at popular sites. This practice is sometimes called credential stuffing, and attackers can be very successful at breaking into sites if users reuse passwords. An added benefit is user productivity and user happiness. Ensure the company’s password manager uses strong encryption to store your passwords securely. Single Sign-On (SSO) is becoming more popular, allowing users to log in once to access multiple sites or resources.

Do you utilize geo-blocking or geo-filtering? These technologies identify computers, users, and email messages based on geographical locations. You will be more secure if you block email and login attempts from geographical areas where you never do business and block user logins from countries without users. While attackers can bypass these protections using VPNs, the protections are still helpful.

Are users local administrators? When you set up a new Windows or Apple computer, the user has local administrator access and can perform many activities, including installing programs. If an attacker manages to compromise that user’s account, the attacker has tremendous power to compromise that computer and potentially your entire organization. This topic is complex, but the goal of every organization must be to ensure all workers are “standard users” on their computers. Being a standard user limits what an attacker can damage and makes the user account more difficult to compromise in the first place. Privilege Access Management (PAM) solutions help manage local admin rights by controlling and monitoring privileged access to critical systems.

Do you segment your network? Network segmentation splits your network into smaller parts based on the purpose or type of device. For example, suppose you isolate your security cameras from your servers on a different network segment, such as a subnet or VLAN. If an attacker breaks into a security camera, segmentation can block their ability to hack your servers through the camera. Common segments include:

-Servers
-Desktops and Laptops
-Wireless Network
-VPN users
-Security cameras
-VoIP systems
-Different floors in your building or different buildings on your campus

It is possible to over-segment and create too much work for your IT Team, but that rarely happens. Your team will set up Access Control List (ACL) rules that limit communications between the segments to block unauthorized activities.

Have you established a security baseline for your systems? Have a documented standard configuration for security controls you enforce on your servers, workstations, and mobile devices.

How soon after release do you apply critical security updates to your devices? Microsoft, Apple, your firewall manufacturer, and other providers release security updates to programs to block attackers from using previously undetected security holes. You must apply the patches quickly to prevent attackers from exploiting the vulnerabilities. Testing patches before deployment is essential to avoid errors. Staging patches allows you to help ensure they don’t disrupt your production network. Zero-day patches and updates fix problems that attackers are already using to compromise systems.

Do you allow workers to use family computers or mobile devices to access email and work from home? Family computers are significantly less secure than company-issued devices that your IT Team manages, monitors and protects 24×7. It is relatively common for organizations to permit users to use their BYOD phones to access company email. Your insurance company could see that as a red flag against providing or renewing a policy. You’ll want to demonstrate other safeguards you use to minimize the risk.

Do you enforce EPP on all devices? Endpoint protection is a tool your IT Team can use to protect each device on your network. Ask your IT Team. Chances are they’ve implemented this solution. They might use Security Information and Event Management (SIEM) to enhance visibility and response. SIEM systems aggregate and analyze activity from different resources across your IT infrastructure.

Do you utilize EDR/XDR tools? Using Endpoint Detection and Response (EDR), Extended Detection and Response (XDR), or Managed Detection and Response (MDR) agents on the laptops can increase security by monitoring for malicious behavior known as an indicator of compromise (IoC). EDR/XDR tools provide many benefits, including continuously monitoring network devices and watching for suspicious activities or evidence that an attacker is compromising a system. EDR/XDR is designed to identify, isolate, and mitigate threats. EDR and XDR must be effectively monitored, managed, and updated. One way many organizations ease the burden on their internal IT Teams is to utilize a third-party MSSP to perform these tasks. Managed Detection and Response (MDR) means you pay a third-party provider to manage your EDR/XDR. One key point to remember is that attackers can also obtain these protection tools and continually seek ways to bypass them. We perform Red Team Exercises at companies to test the capabilities of the EDR and XDR protections. Do not make the common mistake of letting your guard down in other security areas after implementing EDR or XDR.

How frequently do you conduct internal and external security audits, vulnerability assessments, penetration tests, and Red Team Exercises? These tests identify previously undiscovered weaknesses in your security. Please get in touch with us if you need these services as part of a comprehensive security advisory service for executives to help them secure their organizations. We guide and become a resource for your existing IT team rather than replacing them.

Does your spam filter scan messages and attachments for malicious links? If the answer is no, you need to add these features immediately.

Do you use web filtering and DNS filtering? Web filtering features, often integrated with firewalls, allow your IT team to block known malicious sites, gambling, and other categories of websites. Domain Name Service (DNS) maps URL website names to addresses of servers on the web. DNS filtering services strive to identify malicious web servers and automatically block communications from your network to them. As a bonus, some services permit you to hinder users from accessing sites you might deem inappropriate.

Do you use SPF for email messages? The Sender Policy Framework is a protective solution that your IT Team can enable to permit your email servers to confirm that inbound email messages came from an approved server rather than a fraudster impersonating or spoofing a legitimate source. While they are at it, your IT Team can enable DKIM to help other organizations’ mail servers confirm that messages they receive from you are legitimate and unaltered. They can configure DMARC to tell remote email servers to throw away messages from fraudsters attempting to impersonate your organization. It is essential to regularly review your SPF, DKIM, and DMARC records to adapt to the changing configurations and threat landscape.

Do you identify storage locations and isolate PII, PHI, and other sensitive data? Determining where you store Personally Identifiable Information (PII), Protected Health Information (PHI), Cardholder Data (CHD), and other sensitive information is essential. Knowing where to store sensitive information is a fundamental step in protecting it. Do you keep the information isolated and protected? This identification and isolation is becoming even more critical due to the integration of AI into organizations, which might give AI access to company information.

Do you use role-based access control (RBAC) to limit user access based on their job functions, and how do you manage and monitor privileged accounts? Role-Based Access Control (RBAC) ensures that users only have access to the data and systems necessary for their specific job functions. This minimizes the risk of unauthorized access to sensitive information. Privileged accounts with higher access levels are managed through Privilege Access Management (PAM) solutions that monitor and control their use, reducing the risk of misuse or compromise. Regular audits and real-time monitoring of these accounts are essential to detect and respond to suspicious activities.

Do you encrypt sensitive data at rest and in transit, and what encryption standards do you use? Encryption is critical for protecting sensitive data when it is stored (at rest) and transmitted (in transit). Encryption standards such as Advanced Encryption Standard (AES) with 256-bit keys are commonly used to ensure robust security. Data at rest is encrypted to protect it from unauthorized access, even if physical security is breached. Data in transit is encrypted using protocols like TLS (Transport Layer Security) to prevent interception during transmission over networks.

How do you assess and manage third-party vendors’ cybersecurity risks and ensure vendors follow appropriate security practices? Third-party vendors can introduce significant cybersecurity risks. Assessing these risks involves regular security evaluations and audits of the vendors’ practices. It’s important to have contracts that require vendors to follow appropriate security practices tailored to their roles and services. Continuous monitoring and periodic reassessments ensure that vendors maintain the required security posture over time. Organizations can manage risks by working collaboratively with vendors to meet security expectations without imposing stringent certification requirements.

Do you use firewalls, intrusion detection/prevention systems (IDS/IPS), and other network security measures? Firewalls act as a barrier between the internal network and external threats, controlling incoming and outgoing traffic based on predetermined security rules. Intrusion Detection Systems (IDS) and Intrusion Prevention Systems (IPS) monitor network traffic for suspicious activities and take action to prevent potential breaches. These network security measures are crucial for protecting against unauthorized access and cyberattacks.

How do you secure remote access to your network? Securing remote access involves implementing measures such as Virtual Private Networks (VPNs), which encrypt the connection between remote users and the corporate network. Your IT professionals must manage remote devices to help increase security. Multi-factor authentication (MFA) adds an extra layer of security by requiring additional verification steps beyond just a password. Additionally, restricting remote access to only essential personnel and monitoring for unusual login activities are critical components of a secure remote access strategy. This is an extensive topic; please let us know if you want more information.

What physical security measures do you have in place to protect your data centers and offices? Physical security measures are essential to protect data centers and office premises from unauthorized access. These measures include access control systems like key cards or biometric scanners, surveillance cameras, and security personnel. Secure facilities should also have environmental controls such as fire suppression systems and backup power supplies to safeguard against physical threats and disasters. The Foster Institute offers full-scale Physical Red Team Exercises to test your physical security measures.

Are you compliant with relevant regulations and industry standards, such as GDPR, HIPAA, PCI-DSS, or ISO/IEC 27001, and how do you ensure ongoing compliance with these standards? Compliance with regulations and industry standards demonstrates a commitment to maintaining high security and privacy standards. Regular audits and assessments help ensure compliance with frameworks such as GDPR (General Data Protection Regulation), HIPAA (Health Insurance Portability and Accountability Act), PCI-DSS (Payment Card Industry Data Security Standard), and ISO/IEC 27001. Ongoing compliance is maintained through continuous monitoring, employee training, and updates to policies and procedures as standards evolve. Please let us know if you need help with achieving or maintaining compliance. The Foster Institute, Inc. can simplify and manage the process for you.

How do you secure mobile devices employees use to access company data and use mobile device management (MDM) solutions to enforce security policies on mobile devices? Mobile Device Management (MDM) solutions enforce security policies on employees’ mobile devices that access company data. These solutions can remotely manage and secure devices, ensuring they comply with organizational security standards. Features include enforcing strong passwords, encrypting data stored on the device, and remotely wiping data if a device is lost or stolen. This ensures that mobile devices do not become a weak point in the company’s overall security posture.

Do you store backups offline or on immutable storage? If an attacker gains access with the intent of encrypting or deleting data to demand ransom, they might attempt to destroy your ability to restore. They know you’re more likely to pay the ransom if you cannot restore sensitive data. So, you must isolate some backup data so the attacker cannot damage it. It is essential to have backups that threat actors cannot delete or damage if they break into your network. Immutable storage is data stored where you can access it, but no users, not even your administrators, can delete or alter the backup files. Cloud providers, such as Microsoft, offer immutable cloud storage. Other devices use write-once-read-many (WORM) technology to store data immutably. Offline backup is disconnected from your network. Some companies might use backup tapes or hard drives disconnected from the network and store them in a safe location for offline storage. Other organizations have a secondary network, isolated from the primary network, dedicated to their backup servers; the only connection is a server that transfers production network data to the backup network. It is best to store backups in diverse locations for redundancy and eliminate any single points of failure.

Do you encrypt your backups? If an unauthorized person accesses your backup data, it is useless if they cannot read the contents. Encryption is a setting in your backup software. There was a time when people wouldn’t encrypt backups because the backups would take much longer. With today’s technology, there should be little added time.

How often do you practice the restore process? If you have never practiced your complete restore process, do it now. Many organizations find out they cannot restore from their backups. Often, their failed attempt was the first time they’d ever tried to restore. It can be complicated to perform a test restore, so be prepared to give your IT Team additional time. If you outsource your IT, it is understandable that they’ll charge you for practicing the restore. Always perform restore tests in a controlled environment, separate from your production systems.

How long will it take to restore your data from backups? When you practice your complete restore process, measure the time it takes to restore. If you find out the duration is too long, you can take steps to speed up the process.

What steps do you take to prevent ransomware attacks? This space on the insurance application allows you to list the items above in statement form. Almost all security measures you use can protect against ransomware attacks or limit the impact.

Do you have a documented Disaster Recovery Plan (DRP) and Business Continuity Plan (BCP) in place? Documented disaster recovery plans demonstrate that you’ve thought through the processes required to recover from disruptive events. These plans should outline specific procedures for data recovery, system restoration, and maintaining business operations during and after an incident.

Do you conduct disaster recovery drills? Regular drills ensure your team is prepared to execute the DRP and BCP effectively. These drills can be as basic as tabletop exercises, where team members discuss their roles and responses to hypothetical scenarios, or as comprehensive as full-scale exercises that simulate actual disaster conditions and involve all aspects of the organization.

These are some of the most common questions on our customer’s insurance policy application and renewal forms. If you find others, please reach out for guidance.