October is Cybersecurity Awareness Month, and this year’s theme — Building a Cyber Strong America — is a call to action for organizations of every size to strengthen their digital defenses.
Cybersecurity is no longer an issue reserved for governments and global enterprises. In 2025, small and midsize businesses (SMBs) are squarely in the crosshairs of cybercriminals using AI-driven phishing, ransomware, and data theft schemes to exploit vulnerabilities.
IBM reports the U.S. average cost of a data breach could reach a record $10.22 million, and while large corporations can sometimes absorb that hit, many small businesses cannot. In fact, according to the National Cyber Security Alliance, as high as 60 percent of small businesses close within six months of a major cyberattack.
“If you help run a small or mid-sized business, you already know cyber threats are out there. What’s changing — and quickly — is how those threats work,” says managed services provider Secur-Serv. Recent industry reports show that nearly half of SMBs have already faced an AI-enabled cyberattack. And more than 70 percent of small businesses say they’ve experienced at least one security incident in the past year.
The takeaway is clear: prevention and protection must go hand in hand — and cyber insurance is now a critical part of that equation.
The cybersecurity landscape has changed dramatically in just the past few years. Once manual and limited in scale, attacks are now automated, intelligent, and widely accessible through “malware-as-a-service” kits.
Here are some of the trends driving this shift:
Cybercriminals increasingly view smaller firms as “easy entry points” into larger supply chains, vendors, or customers. If your business stores customer data, relies on email, or processes payments online, you’re a potential target.
Cyber insurance provides the financial and operational safety net needed to recover from digital attacks and data breaches. Even with strong cybersecurity measures in place, no system is foolproof — and the consequences of a single breach can be devastating.
A robust cyber insurance policy can help cover:
“Without this coverage, small businesses often shoulder all expenses — legal fees, lost productivity, and reputational harm — on their own,” says Kyle Dean, Dean & Draper President, and CEO.
Not all cyber insurance is the same. Policies typically fall into two categories: first-party (covering your own business losses) and third-party (covering liability to others affected by a breach).
| Coverage Type | What It Protects | Examples of Expenses Covered |
| First-Party | Your business’s direct losses | Data restoration, business interruption, ransomware payments, crisis communications |
| Third-Party | Claims from customers, partners, or regulators | Legal defense, settlements, regulatory fines, negligence claims |
Dean & Draper helps businesses identify where exposure exists across both categories to ensure no coverage gaps remain.
Every small business has different risks depending on size, industry, and technology use. A one-size-fits-all approach won’t cut it.
When designing a cyber insurance policy, Dean & Draper considers key factors such as:
By tailoring coverage, small business owners can ensure protection fits their operations and budget.
Despite its importance, several misconceptions prevent many small businesses from purchasing coverage:
Myth 1: “We’re too small to be targeted.”Myth 2: “Our general liability policy already covers this.”
Myth 3: “Insurance will pay no matter what.”
Myth 4: “Cyber insurance is too expensive.”
While cyber insurance offers vital financial protection, it’s equally important to strengthen your security posture. The Cybersecurity and Infrastructure Security Agency (CISA) recommend these foundational steps:
Pro Tip: Insurers often reward proactive security with lower premiums. Demonstrating employee training, MFA use, and regular data backups can reduce your cyber insurance costs.
This October’s Cybersecurity Awareness Month emphasizes that cybersecurity is a shared responsibility across individuals, businesses, and public infrastructure.
As Homeland Security Secretary Kristi Noem noted, “Every day, bad actors are trying to steal information, sabotage critical infrastructure, and exploit American citizens.”
For small businesses, this means building a culture of cyber awareness:
By taking these steps, you not only reduce your risk but also help protect your customers, community, and the broader digital ecosystem.
Dean & Draper’s insurance professionals understand that small businesses are the backbone of a Cyber Strong America — and that protecting your digital assets is essential to long-term success.
We work closely with business owners to:
Contact Dean & Draper today to learn how cyber insurance for small businesses can safeguard your data, your reputation, and your bottom line.
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