Why Cybercriminals Love the Holiday Season and What Your Business Can Do About It

Most small business owners assume the holiday season is a slow period for cybercrime. The logic makes sense on the surface. Everyone is winding down, wrapping up the year, and getting ready to take a breath. Surely criminals are doing the same.

They are not.

The holiday season is actually one of the most active periods for cyberattacks against small and mid-sized businesses. The FBI’s Internet Crime Complaint Center consistently records a sharp rise in reported incidents in the first quarter of each year, which reflects attacks that took place during November and December. Cybercriminals are not slowing down. They are timing their attacks specifically because they know your team is distracted, your IT coverage is thinner, and your guard is lower than it is any other time of year.

If your business operates in Billings, Bozeman, Missoula, Spokane, or any of the communities Entre serves, this post is worth reading before the holiday season hits. Understanding what attackers are doing and why it works is the first step toward making sure it does not work on you.

Why the Holiday Season Creates the Perfect Opening for Attackers

Before getting into the specific threats, it helps to understand the conditions that make this time of year so attractive to cybercriminals.

Your team is busier than usual and more distracted. Inboxes are flooded. People are rushing to close out year-end work, approve final invoices, and get projects wrapped before they leave for vacation. In that environment, people click faster and verify less.

IT teams and managed service providers are also running leaner during holidays and long weekends. Staff are on vacation. Response times are slower. If an attacker can get a foothold on a Thursday afternoon, they may have an entire long weekend to move through your network before anyone notices something is wrong.

Add to that the fact that many businesses process a high volume of financial transactions at year end, and you have a situation where attackers can do more damage, in less time, with less resistance. They know this. They plan for it.

Phishing Attacks Get More Convincing Every Year

Phishing is the most common entry point for cyberattacks year-round, and during the holidays it becomes even more effective because the volume of legitimate email that looks like phishing goes through the roof.

Your employees are already receiving order confirmations, shipping updates, charity appeals, gift notifications, and promotional emails from dozens of sources every day. Attackers blend into that noise. A fake shipping notification from what appears to be a major carrier. A spoofed invoice from a vendor your company actually uses. An email that looks like it came from your own leadership asking for a quick wire transfer before the end of the quarter.

What makes modern phishing particularly dangerous is how polished it has become. Cybercriminals are using AI tools to write emails that are grammatically clean, contextually accurate, and personalized in ways that would have been impossible a few years ago. The days of spotting a phishing email because of broken English or an obvious fake sender address are largely behind us.

The result is that employees who consider themselves careful are still clicking. And one click is all it takes.

For businesses that want to understand how phishing fits into the broader cybersecurity picture, Entre’s cybersecurity resources cover the threat landscape in plain language built for business owners, not IT professionals.

Ransomware Is Designed to Hit When You Are Not Watching

Ransomware does not just happen randomly. Modern ransomware attacks are deliberate, patient, and timed for maximum impact.

Here is how it typically plays out. An attacker gains access to your network through a phishing email, a weak password, or an unpatched piece of software. Rather than immediately causing damage, they spend days or even weeks moving quietly through your systems, escalating their access and identifying your most critical data. Then, when they are ready, they deploy the ransomware payload and encrypt everything of value.

What makes this especially dangerous during the holidays is the timing of that final step. Attackers frequently schedule ransomware to deploy late on a Friday afternoon, just before a long weekend, or during a holiday period when they know response will be slow. By the time your team realizes what has happened, the damage is already widespread.

For small businesses without 24/7 monitoring in place, the gap between when an attack begins and when someone notices can be long enough to make recovery extremely difficult. This is exactly why network security monitoring and a tested backup and recovery solution are not optional extras. They are the difference between a bad day and a business-ending event.

Industries like healthcare, banking and financial services, and law firms face additional exposure because ransomware attacks in these environments do not just disrupt operations. They trigger compliance obligations, mandatory reporting requirements, and potential regulatory penalties on top of the recovery costs.

Business Email Compromise Is Quietly One of the Costliest Threats

Ransomware gets most of the attention, but business email compromise causes more financial damage to small businesses than almost any other type of attack, and it rarely involves any malware at all.

The way it works is straightforward. An attacker either hacks into a legitimate business email account or creates one that looks nearly identical to a real one. They then use that account to send emails to someone inside your organization, usually someone in finance or operations, requesting a wire transfer, a change to banking details on an invoice, or access to sensitive information.

During the holiday season, this attack becomes more effective for a few specific reasons. Executives are frequently out of the office, which makes it harder for employees to quickly verify an unusual request in person. Finance teams are processing a higher than normal volume of year-end payments, which creates more opportunities for a fraudulent transaction to slip through. And the general rush of the season means people are less likely to pause and question something that looks legitimate.

A single successful business email compromise attack can cost a small business tens of thousands of dollars, most of which is very difficult to recover. The businesses that avoid it are the ones that have clear verification processes in place and employees who know to follow them even when things feel rushed.

Credential Theft Spikes When Employees Are Using Personal Devices

The holidays also bring an increase in credential stuffing attacks, which is when cybercriminals take usernames and passwords stolen from one platform and try them across dozens of others.

This works more often than it should because people reuse passwords. An employee might use the same password for a retail account they signed up for years ago as they do for their work email or your company’s project management software. When that retail site experiences a data breach and those credentials end up for sale on the dark web, attackers will systematically try them against business applications, VPNs, and cloud platforms until something opens.

During the holidays this risk increases because employees are more likely to be logging into work systems from personal devices, home networks, and public Wi-Fi. Each of those scenarios introduces additional exposure that does not exist in a properly managed office environment.

Multi-factor authentication is the most effective single defense against credential-based attacks. Even if an attacker has a valid username and password, they cannot get in without the second verification step. It is one of the first things Entre recommends as part of any complete IT management engagement.

What Your Business Should Have in Place Before the Holiday Season

Knowing the threats is only useful if it leads to action. Here is what actually reduces your risk during this period.

Train Your Team Before the Rush Starts

Security awareness is not a one-time onboarding topic. It needs to be reinforced regularly, and the period just before the holidays is one of the most important times to do it. A short reminder to your team about what holiday phishing looks like, how to verify unusual financial requests, and what to do if something feels off can prevent a significant incident.

People are not careless. They are busy. A timely reminder gives them the context they need to slow down at the right moment.

Make Sure Your Backups Are Tested, Not Just Running

A lot of small businesses have backup systems in place that have never actually been tested. Data is copying somewhere, but nobody has confirmed that the restore process works, that all critical systems are covered, or that the recovery time is acceptable.

Before the holiday season, verify your backups. Run a test restore. Confirm that your backup solution covers everything it needs to cover and that someone knows exactly what to do if a restore becomes necessary. A backup that has never been tested is a false sense of security.

Patch and Update Everything Before Staff Leave

Attackers actively scan for unpatched systems, and the holiday period is prime time for that kind of reconnaissance. Before your team goes on vacation, make sure operating systems, software, and firmware are all updated. Disable any remote access tools or user accounts that are not actively needed. Close the doors that do not need to be open.

Have a Response Plan That Does Not Depend on Everyone Being in the Office

If something happens during a holiday weekend, who gets called? Who has the authority to make decisions? Who contacts clients if data is exposed? These are questions that need answers before the incident, not during it.

A documented incident response plan does not need to be complicated. It just needs to exist and be accessible to the right people.

Consider Whether Your Current IT Coverage Is Actually Sufficient

For small businesses managing IT internally or relying on a part-time resource, the holiday season exposes a real gap. If your IT coverage depends on one or two people who are also taking time off, you may have stretches where nobody is actively watching your systems.

This is one of the most practical reasons businesses in Billings, Spokane, Great Falls, Helena, Kalispell, Butte, Coeur d’Alene, Cody, and Missoula work with a managed IT partner. Not because they cannot handle day-to-day IT on their own, but because consistent coverage during high-risk periods requires infrastructure and staffing that most small businesses cannot maintain alone.

The Holiday Season Is a Test Your IT Setup Either Passes or Fails

You will not always know your defenses held until after the fact. But businesses that go into the holiday season with proper monitoring, tested backups, trained employees, and a response plan in place are in a fundamentally different position than those that are just hoping nothing goes wrong.