As the holiday season approaches, businesses of all sizes are preparing for the festive rush. But alongside the celebrations, there’s another annual ritual quietly unfolding in the background. Cybercriminals crafting their own set of “gifts” for your organization.
For security and IT teams running mission-critical operations, this time of year is especially high-stakes. Reduced staffing, heavier online activity, and constant infrastructure changes can quickly widen your exposure window – just when your organization can least afford downtime or data loss.
In this post, we’ll look at why cyberattacks spike during the festive season, what makes modern environments particularly vulnerable, and how internal security teams can use continuous testing, faster reporting, and tighter collaboration with engineering to keep the holidays incident-free.
Why Do Threat Actors Love the Holidays?
To start off, let’s explain why for many teams this might be the season of giving and winding down – but for cybercriminals, it’s the season of taking.
According to a Darktrace research, cyber attacks, especially ransomware, can increase by a staggering 70% during the holiday months of November and December compared to January and February. This isn't a coincidence, but a calculated exploitation of unique seasonal vulnerabilities, caused by a number of factors like:
Understaffed IT Departments
The recent Semperis 2024 Ransomware Holiday Risk Report finds that 90% of the US organizations surveyed reduce their IT security staff during holiday periods by as much as 50%. This skeleton crew approach creates critical monitoring gaps that hackers conveniently exploit, knowing that response times will be significantly delayed, increasing the financial and reputational impact on organizations.
Emotional Consumer Behavior
Another addition to the attackers’ paradise is the shopping madness, which results in an increase of US holiday spending with each passing year. This might be great for the economy, yet the massive surge in digital transactions creates a target-rich environment for cybercriminals. The attackers often take advantage of the emotional urgency the holiday shopping drives, which makes individuals more likely to click suspicious links or provide sensitive information.
Тhey send fraudulent emails offering “too good to be true” promotions and fake shipping notifications, often pumping these scams out to email addresses on an industrial scale. In fact, last holiday season, Bitfender has found that 3 out of every 4 Black Friday themed marketing “spam” emails are actually scam, intended to defraud consumers of their money or even install malware on their device to steal credentials or data.
Remote Work Complications
Flexible work arrangements during the holidays add to the complexity – with most companies maintaining remote holiday work arrangements, networks also become more porous. Personal devices, unsecured home networks, and reduced corporate oversight create multiple entry points for potential breaches.
3 Essential Security Moves to Keep Your Organization Merry and Safe
The question becomes: how do you stay in control when the business is at its busiest, and your team is at its thinnest?
Here are three practical moves that help you reduce exposure windows and keep critical systems secure throughout the holiday season.
1. Check Your Systems Twice – and Keep Testing Continuously
In a world where infrastructure changes daily and new vulnerabilities appear by the hour, an annual or even quarterly penetration test simply isn’t enough. By the time a traditional report lands on your desk, parts of your environment have already changed.
Instead, treat pentesting as a continuous control, not a once-a-year checkbox. That means:
- Running smaller, targeted tests more frequently, especially around high-change systems and peak business periods.
- Triggering tests when something important changes – a new internet-facing app, a major code release, a new integration with a third party.
- Giving your team a unified view of assets, findings, and risk across environments so they can see where the real exposure is right now.
With the right platform, you can combine automation (for discovery, enrichment, and scoping) with human expertise (for validation and real-world attack paths). The result: your team spots and prioritizes issues earlier, instead of finding them in a retrospective report long after the holidays are over.
2. Wrap Up Reporting Faster – and Make It Actionable
During the holidays, time-to-insight matters just as much as time-to-detect. If your team spends days manually assembling reports, that’s time stolen from actually fixing issues.
Accelerated, automated reporting changes this dynamic by:
- Capturing evidence, steps, and findings as tests run, not as a separate project afterward.
- Generating audit-grade, board-ready reports on demand – complete with severity, business impact, and remediation guidance.
- Providing consistent, comparable metrics across tests, projects, and business units so you can demonstrate progress over time.
This isn’t just about speed for its own sake. Fast, structured reporting gives you a bridge between technical work and executive decisions. It helps you walk into holiday change-control meetings, risk committees, or customer audits with clear proof of what’s been tested, what was found, and how quickly it’s being addressed.
3. Communicate Fast, Fix Faster
Identifying vulnerabilities is only half the battle. The real win is how quickly you can get the right people to fix the right problems – especially when teams are dispersed, on reduced schedules, or juggling incident queues.
To shrink exposure windows during the holidays, focus on tightening the loop between discovery and remediation:
- Integrate findings directly into your existing workflows (e.g., Jira, ServiceNow, Slack, or email) so engineers and owners see issues in the tools they already live in.
- Use clear prioritization and ownership – who owns this vulnerability, what’s the SLA, what’s the potential business impact if it waits until January?
- Maintain real-time visibility into remediation status so security, IT, and leadership know what’s open, what’s in progress, and what’s resolved.
When communication and remediation are streamlined, your team can move from “we’ll handle it after the holidays” to “we identified it today and it’s already in progress.” That shift alone can be the difference between a quiet festive season and a headline-making incident.
Silent Nights, Secure Systems
During the holidays, cybercriminals aren’t taking time off – and the risks to digital infrastructure are anything but festive. Reduced staffing, heavier online activity, and constant change across applications and cloud environments mean that a single overlooked vulnerability can quickly turn into a very public incident.
But this season is also an opportunity for security and IT leaders to show the business what “good” looks like:
- treating pentesting as a continuous, always-on control,
- turning findings into fixes faster,
- and proving to customers, partners, and auditors that security isn’t a once-a-year exercise, but a year-round discipline.
By leaning into continuous testing, accelerated reporting, and tighter collaboration with engineering, you can move from reactive fire-fighting to proactive risk reduction – not just in December, but every month of the year.
Ready to Keep the Grinches Out All Year Round?
Book a demo today and see how Plainsea’s platform for AI-driven, continuous pentesting can help your organization stay secure through the holidays – and keep those Grinch-like threats out of your environment all year round.