Cyber Security: Assessing and Mitigating Your Cyber Risk ASL S6, E11

 

In the latest episode of Castle Group’s Association Leadership Webinar Series (Season 6, Episode 11), an expert panel tackled one of the most pressing challenges facing community associations today: cyber risk. As digital threats grow more sophisticated and widespread, the session—titled “Assessing and Mitigating Your Cyber Risk”—offered practical insights into identifying vulnerabilities and strengthening safeguards. Hosted by Castle Group, the webinar featured Craig Vaughan, Chief Financial Officer at Castle Group; Kevin Davis, President of Kevin Davis Insurance Services; Jeffrey Rembaum, Esq., of Kaye Bender Rembaum, P.L.; and Sean Kalinich, Chief Information Security Officer at Kinetix Solutions. 

Regulatory Compliance and Insurance Requirements:  

The session opened with a critical update on Florida’s legislative mandates. Condominium associations must now create and maintain an online account with the Division of Florida Condominiums, Timeshares, and Mobile Homes by October 1. This registration includes property details and construction data. Associations are advised to consult legal counsel regarding the submission of optional data points. 

Insurance compliance was another key point. Condos are required to maintain adequate property insurance based on independent appraisals conducted at least every three years. The legal standard of “best efforts” applies, setting a high bar for boards to justify insurance decisions. Homeowners associations (HOAs) must refer to their declarations for insurance obligations, with “reasonable business judgment” serving as the guiding principle. 

Understanding Cyber Risk in Community Associations 

Only a third of webinar attendees had formally considered their exposure to a cybersecurity incident. Sean Kalinich, Chief Information Security Officer at Kinetics Solutions, described a cybersecurity audit as a top-down analysis of an organization’s infrastructure, devices, applications, and users. These audits evaluate risk and exposure levels, identify gaps, and recommend tools to close those gaps. 

The three most common vulnerabilities identified were: 

1. Identity Exploitation: Including compromised credentials or unauthorized device access. 

1. Insecure Endpoints: Unprotected devices like personal laptops or phones used to access systems. 

1. Misconfigurations: Improperly set systems that leave the door open for attackers. 

Social engineering was cited as the most common method used by cybercriminals. Attackers create urgency and impersonate trusted individuals, such as board members or vendors, to manipulate users into transferring funds or revealing sensitive information. 

While cybersecurity teams hold much of the responsibility, user awareness remains critical. Regular training, phishing simulations, and the principle of “if it feels wrong, it probably is” can prevent many incidents. On the technical side, organizations should employ Identity Detection and Threat Response (IDTR) systems and Endpoint Detection and Response (EDR) tools. These systems flag anomalies like impossible travel or unauthorized logins and automatically contain threats. 

Why Associations Need Cyber Insurance 

Kevin Davis of Worldwide Insurance Services emphasized the dual nature of cyber threats: theft of personal data and financial fraud. Associations are attractive targets due to large reserve funds and limited technical defenses. He outlined two primary types of loss: 

• Identity Theft and Data Breach 

• Financial Loss via Social Engineering 

Traditional insurance packages offer limited coverage. Social engineering attacks, now insurable under specialized crime or cyber policies, were previously excluded. Cyber insurance policies also cover post-breach costs such as breach counsel, call centers, notifications, and forensic investigations, which can easily exceed $250,000. 

Cost and Coverage 

Cyber insurance is surprisingly affordable. Social engineering coverage can be added to a crime policy for as little as $50 to $100 annually. A standalone cyber policy starts around $500 and goes up depending on coverage limits. Associations are encouraged to insure for the total value of their reserves and at least three months of operating expenses. 

Incident Response Playbook 

In the event of a cyber incident, associations should: 

• Notify their insurance carrier immediately 

• Engage breach counsel to preserve privilege and manage communications 

• Lock down the point of entry (email, phone, user account) 

• Avoid deleting evidence 

• Contact their cybersecurity provider for immediate triage 

Conclusion 

Community associations must take proactive steps to mitigate cyber risk. From improving awareness to investing in technology and insurance, the path forward involves collaboration between managers, boards, legal counsel, and IT experts. The tools and coverage are available; the key is taking action before an incident occurs. 

To watch the full webinar on Cyber Security: Assessing and Mitigating Your Cyber Risk, visit ASL S6,E11: Cyber Security: Assessing and Mitigating Your Cyber Risk.  

To learn more about how Castle Group can serve your community, request a proposal at https://castlegroup.com/request-a-proposal/.     

Tags: