Making a List, Checking It Twice: Is Cyber Coverage on Yours?

The holidays can bring plenty of opportunities for businesses, but they can also bring added cyber risk, making now the perfect time to review your cybersecurity safeguards and coverage.

While businesses prepare for increased sales, seasonal staffing, year-end reporting, and holiday promotions, cybercriminals are preparing, too. A surge in online transactions, crowded inboxes, temporary employees, and limited holiday staffing can create opportunities for phishing scams, payment fraud, ransomware, and data breaches.

Just as you prepare your inventory and operations for the year-end rush, protecting your digital assets requires a proactive plan. As you check items off your holiday to-do list, make sure cybersecurity and cyber insurance coverage are included.

Holiday Cheer for Businesses, Opportunity for Cybercriminals

The holiday season creates unique cybersecurity challenges for organizations of all sizes. With more transactions, customer interactions, and year-end activity taking place, businesses often become more attractive targets for cybercriminals.

Common holiday-related cyber threats may include:

Phishing emails disguised as shipping notifications, invoices, or holiday promotions.
Fraudulent payment requests targeting accounting and finance employees.
Credential theft through phony login pages.
Business email compromise schemes that impersonate executives or vendors.
Ransomware attacks intended to disrupt operations during busy periods or when IT staffing is limited.

One successful attack can lead to financial losses, operational downtime, reputational damage, and potential legal or regulatory consequences. Fortunately, a few practical precautions can help your business reduce its exposure.

Your Holiday Cybersecurity Checklist

Before the holiday rush begins, review your organization’s cybersecurity practices and identify areas that may need additional attention.

Train Employees to Recognize Seasonal Scams

Holiday inboxes can quickly fill with legitimate invoices, shipping updates, vendor promotions, and payment requests. Cybercriminals take advantage of this activity by creating fraudulent messages that closely resemble the real thing.

Remind employees, including seasonal team members, to examine sender addresses, links, attachments, invoices, and unexpected payment requests carefully. Employees should verify unusual requests through a trusted communication channel before sharing information, transferring funds, or opening a link.

Add Another Lock with Multi-Factor Authentication

Multi-factor authentication, commonly called MFA, provides an additional layer of protection for important business accounts. If a password is stolen through a phishing scheme or fraudulent login page, MFA may help prevent an unauthorized user from gaining access.

Consider enabling MFA for email, financial platforms, cloud applications, administrative accounts, and other systems that contain sensitive information.

Review Accounts and Access Permissions

Seasonal staffing and year-end transitions can leave businesses with outdated accounts or unnecessary system access. Review who can access sensitive data and critical systems, remove inactive accounts, and limit permissions to what each employee needs to perform their job.

As seasonal employees complete their assignments, make sure their user accounts, logins, passwords, and access permissions are disabled or deleted promptly. This includes access to email, company networks, cloud-based applications, point-of-sale systems, shared files, and other business platforms. It’s also a good opportunity to confirm that former employees and contractors no longer have access to company systems.

Secure Point-of-Sale Systems and Wi-Fi Networks

Higher transaction volumes can make point-of-sale systems an appealing target during the holidays. Keep point-of-sale software, operating systems, antivirus programs, and other security applications updated with the latest security patches.

If your business offers public Wi-Fi, separate it from the internal network used by employees, company computers, and point-of-sale equipment. Customers and guests should not connect to the same network that supports critical business operations.

Back Up Critical Business Data

Ransomware can prevent a business from accessing essential files or systems, potentially disrupting operations during a critical sales period. Maintain secure backups of important business data, test your recovery process regularly, and avoid storing all critical data and backups in a single location.

Consider keeping backup copies in separate locations, with at least one copy offline or isolated from your primary network. That way, if your main systems or one storage location is affected, you have another source available to support recovery. Separating your backups from your primary systems can provide an additional layer of protection and help your business get back up and running more efficiently.

Prepare for Reduced Holiday Staffing

Cybercriminals may attempt attacks when fewer employees are available to identify and respond to suspicious activity. Before employees take time off, confirm who will monitor security alerts, respond to potential incidents, and communicate with customers, vendors, or other stakeholders if a problem occurs.

An incident response plan should clearly identify contacts, responsibilities, and the steps employees should take when they detect a possible threat.

Is Your Cyber Insurance Coverage Ready for the Holidays?

Strong cybersecurity practices are essential, but no combination of training, software, and internal controls can eliminate every risk. Cyber insurance can serve as an important component of a broader risk management strategy by helping businesses recover from covered cyber-related losses. Because coverage options, exclusions, and limits vary, business owners should periodically review their policies to ensure they align with the organization’s current operations, technology, and data exposure.

Depending on the policy and circumstances, cyber coverage may help address covered costs associated with:

Data breach notification expenses.
Legal services and regulatory support.
Credit monitoring services.
Digital forensic investigations.
Cyber extortion and ransomware events.
Privacy liability claims.
Business interruption losses.
Costs associated with identifying and repairing network vulnerabilities.

Businesses change throughout the year. They may add employees, vendors, software, payment systems, customer databases, or online services. Reviewing coverage before the holidays can help identify potential gaps before an incident occurs.

Check Cyber Protection Off Your List

When you make your holiday checklist this year, put cybersecurity alongside seasonal staffing, inventory, promotions, and year-end planning.

By taking a proactive approach to cybersecurity and reviewing your cyber insurance coverage, your business can be better prepared for seasonal threats and unexpected disruptions. Understanding what your policy covers can also help you prepare for the financial and operational impacts of a cyber incident.

The best time to prepare for a cyber incident is before it happens. Taking steps now can help protect your employees, customers, finances, and operations, allowing you to focus on what matters most: serving your customers and running your business with confidence throughout the holiday season and beyond.

Related Categories

Fraud & Cyber Security Insurance

Kevin Witcher

Kevin Witcher joined SWBC in 2022. He serves as Chief Executive Officer of SWBC Insurance Services. In this role, he is responsible for all operational, business development, and sales activities for the division. Kevin is a seasoned insurance professional with over 34 years of experience. He began his career with Chubb in 1989 after graduating from The University of Texas at Austin. He focused on professional liability for the first 15 years of his career, and he has deep expertise in Directors and Officers liability, crime insurance, fiduciary liability, cyber liability, and employment practices coverages. Kevin served as a Regional Financial Lines Manager overseeing Texas and Oklahoma before moving into a marketing role that included all property and casualty products, as well as personal lines. He then served as Vice President and Branch Manager for Chubb’s Austin Branch, which included Austin, San Antonio, and the western side of Texas. Kevin has served on numerous nonprofit boards, including holding the role of treasurer and board chair for AIDS Services of Austin, as well as the Executive Committee and Board Trustee for Zach Scott Theatre.