The New Reality of Cyber Insurance Requirements for Small Businesses
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The New Reality of Cyber Insurance Requirements for Small Businesses

Cyber insurance used to feel like a safety net. Today, it’s starting to feel more like an application for a mortgage.

Across the country, insurance providers are tightening requirements, raising premiums, and even denying claims when businesses don’t meet modern cybersecurity standards. Many small and mid-sized organizations are discovering this shift the hard way, during policy renewal or after filing a claim.

Whether your business already has cyber insurance or is exploring coverage, here’s what’s changing and what you need to know.

Cyberattacks Are More Expensive Than Ever

Ransomware, phishing, and data breaches have grown dramatically in both frequency and cost. For insurers, the math has changed.

Claims related to ransomware and business email compromise have skyrocketed in recent years, costing insurers billions of dollars annually. As a result, cyber insurance providers are no longer willing to insure businesses that don’t demonstrate strong security practices. In short, cyber insurance is shifting from reactive coverage to proof of prevention.

Security Questionnaires Are Becoming Much More Detailed

If you’ve applied for cyber insurance recently, you may have noticed the application looks very different from what it did just a few years ago.

Today’s questionnaires often ask about:

  • Multi-factor authentication (MFA)
  • Endpoint detection and response (EDR)
  • Patch management and system updates
  • Employee security awareness training
  • Backup and disaster recovery practices
  • Email filtering and phishing protection
  • 24/7 monitoring and incident response
  • Remote access and VPN security
  • Administrative privilege controls

These aren’t just checkboxes. Insurers increasingly require proof that these controls are actually in place.

Premiums Are Rising…and Coverage Is Shrinking

Businesses are seeing:

  • Higher deductibles
  • Lower coverage limits
  • Increased premiums
  • More exclusions and conditions

Some organizations are even being denied coverage entirely if they cannot meet baseline security standards.

For many insurers, the question has shifted from “Do you want coverage?” to “Can you prove you are a lower risk?”

Claims Are Being Denied Due to Weak Security

This is one of the biggest changes that many businesses don’t realize.

If an investigation finds that required safeguards were not in place — or were misrepresented — claims may be reduced or denied.

Examples include:

  • No MFA enabled on email or remote access
  • Backups that were not tested or recoverable
  • Outdated or unpatched systems
  • Lack of employee security training
  • Shared or compromised credentials

Cyber insurance is no longer a substitute for cybersecurity. It is a partner to it.

Cyber Insurance Now Assumes a “Shared Responsibility” Model

Think of cyber insurance the same way you think of property insurance.

A fire insurance policy doesn’t replace smoke detectors, sprinklers, or safe wiring. It assumes you’ve taken reasonable precautions to reduce risk.

Cyber insurance works the same way. Insurers expect businesses to implement foundational security controls before coverage begins.

This shift is forcing many organizations to rethink how they manage technology and risk.

How Managed Security Helps Businesses Qualify

Meeting modern cyber insurance requirements can feel overwhelming, especially for small and mid-sized businesses without a dedicated IT or security team.

This is where managed IT and cybersecurity services play a critical role.

A proactive technology partner can help implement and maintain the controls insurers expect, including:

  • Continuous network monitoring
  • Patch and vulnerability management
  • Endpoint protection and threat detection
  • Secure backup and disaster recovery
  • Email security and phishing protection
  • Security awareness training
  • Access and identity management
  • Documentation for insurance questionnaires and audits

Instead of scrambling during renewal season, businesses can approach cyber insurance with confidence.

How Citynet Helps Businesses Meet Modern Cyber Insurance Requirements

As cyber insurance requirements evolve, many businesses are discovering they need more than basic IT support. They need a proactive technology partner who understands both cybersecurity and business risk.

Citynet’s managed IT and cybersecurity solutions are designed to help organizations build the security foundations insurers now expect, including:

  • 24/7 monitoring and proactive threat detection
  • Managed endpoint protection and patch management
  • Secure backup and disaster recovery solutions
  • Advanced email security and phishing protection
  • Security awareness training for employees
  • Access and identity management best practices
  • Documentation and guidance to support cyber insurance questionnaires

Instead of scrambling to meet new requirements at renewal time, businesses can move forward with confidence knowing their technology environment is being actively protected and professionally managed.

Citynet helps businesses reduce risk, strengthen security, and prepare for the evolving expectations of today’s cyber insurance providers.

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Citynet and Red Siege Webinar Inside the Attacker's Playbook
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Citynet and Red Siege Webinar Inside the Attacker's Playbook

Cybersecurity isn’t just about defense — it’s about understanding how real attackers think.

Join Citynet’s Craig Behr and Red Siege’s Tim Medin for an upcoming webinar, Inside the Attacker’s Playbook, where we’ll break down how real-world offensive operations uncover gaps — and how organizations can use those insights to reduce cyber risk before it becomes a business problem.

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Cyber Protection During Tax Season: What You Need to Know
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Cyber Protection During Tax Season: What You Need to Know

Tax season is stressful enough without worrying about cybercriminals. Unfortunately, this time of year is one of the busiest for online scams, phishing attacks, and data theft, targeting both households and businesses.

From fake IRS emails to stolen login credentials and compromised devices, cybercriminals know tax season creates urgency and confusion, making it the perfect opportunity to strike. The good news? A few smart precautions — and the right technology foundation — can dramatically reduce your risk.

Why Tax Season Attracts Cybercriminals

Tax-related data is extremely valuable. Social Security numbers, bank account details, employer information, and login credentials can all be exploited for identity theft or financial fraud.

Common tax-season threats include:

  • Phishing emails pretending to be from the IRS, tax software providers, or payroll services
  • Fake refund notifications urging you to “act now”
  • Malicious attachments or links that install malware
  • Credential theft from unsecured devices or networks

These attacks don’t just target large organizations. Small businesses, remote workers, and individuals are often seen as easier targets.

Legitimate Communications Still Require Extra Caution

Not every risk during tax season comes from a scam. Legitimate communications from banks, investment firms, employers, and tax providers often contain — or provide access to — highly sensitive information, whether delivered digitally or by mail.

To reduce exposure:

  • Be cautious with links in legitimate emails. Even trusted senders can be spoofed or compromised. When possible, access financial and tax accounts by typing the website address directly into your browser instead of clicking links.
  • Limit sensitive information stored in your inbox. Use secure online portals or paperless delivery options where documents are accessed only after logging in.
  • Protect physical mail and documents. Tax forms, bank statements, and investment records sent by mail should be retrieved promptly and stored securely.
  • Dispose of documents properly. Shred hard copies containing personal or financial information instead of throwing them away intact.
  • Avoid leaving documents unattended. Sensitive paperwork should not be left on desks, printers, or in shared spaces.

These extra precautions help reduce the risk of accidental exposure during a time of year when financial data is frequently shared.

Filing Early Can Reduce Security Risk

Filing your taxes early isn’t just about getting a refund sooner — it can also reduce your exposure to fraud.

Cybercriminals sometimes attempt to file fraudulent tax returns using stolen personal information. When a legitimate return is filed first, it becomes much harder for criminals to succeed.

Additional security benefits of filing early include:

  • Fewer weeks of sensitive data being shared, stored, or transmitted
  • Less last-minute pressure, which can lead to rushed decisions or missed warning signs
  • More time to identify and respond to suspicious activity if it occurs

Filing early, combined with secure online access and good cybersecurity practices, helps limit opportunities for tax-related fraud.

Warning Signs of Tax-Related Scams

Be cautious if you see:

  • Emails or texts demanding immediate action
  • Messages threatening penalties or arrest
  • Requests for sensitive information via email or text
  • Links that look official but lead to unfamiliar websites

The IRS and legitimate tax professionals will never ask for sensitive information through unsolicited messages.

How to Protect Yourself During Tax Season

Whether you’re filing personal taxes or managing business finances, these steps can help keep your data secure:

  1. Secure Your Internet Connection – A reliable, high-speed fiber connection isn’t just about speed — it supports secure data transfers, faster updates, and stronger protection for connected devices.
  2. Use Multi-Factor Authentication (MFA) – Enable MFA on tax software, email accounts, and financial platforms whenever possible. Even if a password is compromised, MFA adds a critical layer of protection.
  3. Keep Devices Updated – Unpatched systems are a favorite target for attackers. Regular updates help close security gaps before they can be exploited.
  4. Be Careful with Links and Attachments – If you didn’t expect it, don’t click it. When in doubt, go directly to the official website instead of using a link in a message.
  5. Back Up Important Data

Accidental deletions, ransomware, or system failures can be devastating during tax season. Secure backups ensure you can recover quickly if something goes wrong.

Key Tax Season Risks for Businesses

For businesses, tax season often means:
  • Increased sharing of sensitive employee data
  • Payroll processing and reporting
  • Communication with accountants and third parties
This makes it especially important to have:
  • Secure email and endpoint protection
  • Monitoring for suspicious activity
  • Backup and recovery solutions
  • Clear cybersecurity policies for employees
Proactive managed IT and cybersecurity services can help prevent issues before they disrupt operations.  Learn more >

What if Identity Theft Happens to You?

From consumer.ftc.gov

  •  Visit IdentityTheft.gov to report identity theft to the FTC and get a personal recovery plan.
  • IdentityTheft.gov walks you through recovery steps for more than 30 types of identity theft.

The Citynet Difference: Connect. Protect. Perfect.

At Citynet, cybersecurity starts with a strong foundation. Our fiber network delivers the speed, reliability, and performance modern homes and businesses need — while our managed IT and cybersecurity solutions help protect your data, systems, and reputation.

With proactive monitoring, layered security, and expert support, Citynet helps organizations stay connected and protected…during tax season and all year long.

Because when it comes to your data, security should never be an afterthought.