Cyber Readiness for The Upcoming Holiday Season

The holiday season is approaching fast and most businesses are getting ready for their busiest time of the year. Orders pick up, customers shop more, and most online activities increase. It is an exciting and often profitable time, but it also brings new challenges. While your team is focused on meeting demand and serving customers, cybercriminals are focused on finding ways to take advantage of the rush.

Let’s discuss how you can get ready for the busy season ahead and beyond.

The Seasonal Increase in Cyber Threats

Each year, there is a noticeable increase in phishing emails, many ransomware attacks, and online fraud during November and December. With so many people shopping online and businesses processing more digital payments than usual, the opportunities for cybercrime multiply.

Cybercriminals take advantage of the holiday rush by sending fake shipping confirmations, delivery scams, or emails that look like they come from trusted vendors or company leaders. Some even hide harmful links in digital holiday cards. These scams are getting harder to spot, even for people who are tech-savvy and know what to look for.

All it takes is one click from an employee to accidentally infect your system or expose sensitive customer data.

How to Keep Your Business Cyber Ready

At Waypoint, we want to make sure your business is ready and can prevent these types of incidents from happening. Here are six expert tips to keep your business cyber-ready at all times.

1. Update and Patch Systems

Before the holiday rush begins, make sure every device and system is up to date. This includes computers, point-of-sale systems, servers, and any software your team uses daily. Updates often contain security patches that fix known weaknesses hackers can exploit. If you have not updated your systems in a while, schedule this before the busiest sales days.

2. Strengthen Your Access Controls

Access control means managing who can log in to your systems and what they can see once inside. Start by enabling multifactor authentication for all accounts. This adds an extra layer of security beyond just passwords.

It is also important to use strong, unique passwords and avoid sharing them between accounts, train your team in creating strong passwords or depending on your structure, set them for your team members. Review who has access to what, especially if you are bringing in temporary team members for the season.

3. Train Your Team

You do not need a complicated training program. A short meeting or an online session can make a big difference. Checklists can also be helpful. Teach them how to recognize phishing emails, how to verify suspicious requests, and what to do if they think something doesn’t look quite right. Most importantly, teach them to never click on anything when unsure. Encouraging an open-door policy where everyone feels comfortable reporting possible threats is critical.

4. Back Up Critical Data

Imagine losing access to all your customer orders, invoices, or financial records during your busiest week. That doesn’t sound good, does it? Regular backups are one of the most effective ways to protect against that.

Set up automated backups for important files and store copies in a secure cloud or offline location. Make sure those backups are encrypted and tested regularly. There is nothing worse than discovering a backup does not work when you actually need it.

5. Review Your Cyber Insurance Coverage

Even with the strongest security, no system is completely foolproof. Cyber insurance is an important layer of protection that can help cover financial losses related to data breaches, ransomware, and business interruptions.

Take time now to review your policy with your insurance provider.

6. Monitor for Unusual Activity

During busy times, it is easy to overlook warning signs. Make it a habit to monitor your systems for anything unusual, such as unexpected logins, unexplained traffic spikes, or sudden changes in vendor payment information. Cybercriminals often test the waters with small, subtle actions before launching a larger attack

A Quick Checklist Before the Holiday Rush

Here is a simple checklist to review before the busy season begins.

• All systems and software updated
• Multifactor authentication enabled for every account
• Staff trained on how to spot phishing attempts
• Data backups tested and stored securely
• Incident response plan reviewed and ready
• Cyber insurance policy reviewed and up to date

Completing these steps by following this article will help your team stay alert and confident during the holidays. It also sends a clear message to your customers that their information is safe with you.

Staying Secure Into the New Year

Being cyber-ready is not just about protecting your business during the holidays. It is about building habits and systems that keep you safe all year long. Once the season is over, take a few minutes to reflect on what worked well and what could be improved.

Cyber readiness is an ongoing process. Threats evolve constantly, and so should your defenses. Keeping your software updated, reviewing access regularly, and providing continuous training can make a lasting difference.

Build a Culture of Cyber Awareness

Creating a culture where cybersecurity is part of everyday operations is one of the best things you can do for your business. When everyone feels responsible for keeping the company safe, your overall protection becomes much stronger. Cybersecurity is not just an IT task. It is a shared responsibility.

Partnering With the Right Experts

You do not have to face cyber risks alone. Partnering with professionals who understand the challenges businesses face during the holidays can give you peace of mind. Our team can help you understand your insurance policy, improve your protection, and know what to do if something happens.

You’re Now Ready

Now that you have our tips in hand, the holiday season should be a time of growth and celebration, not stress over digital threats. Taking proactive steps now can prevent costly incidents later. Simple actions like updating software, training your team, and backing up data can protect your business from major disruptions.

Cyber readiness is about being prepared, staying alert, and knowing you have the right support if and when something goes wrong. By putting these measures in place, you can move into the busiest season with confidence, keeping your customers’ trust and your operations running smoothly.

At Waypoint Insurance, we are here to help you stay secure this holiday season and beyond.