Cybersecurity: The Digital Chess Match (Played Over the Holidays)

If ever there was a perfect time for cybercriminals to strike, it would be the holidays. With security teams scattered, offices running on skeleton crews, and junior staff left manning the fort, the scene is practically begging for disaster. Think of it as the cybersecurity equivalent of leaving your house unattended with a wide-open door and a sign that says, “Gone fishing, help yourself.”

Let’s unpack this curious convergence of holiday cheer and cyber chaos with the patient wit and mild exasperation this topic deserves. After all, nothing says “season’s greetings” quite like a carefully orchestrated attack on your company’s infrastructure.

The Art of Waiting: Attackers, Slack Channels, and the Long Game

Picture this: Somewhere in the dark recesses of a corporate Slack channel, an attacker lurks. They’re not doing anything obvious, mind you—no cackling or villainous monologues. Instead, they’re quietly observing, taking notes on the who’s who of the office, tracking vacation schedules, and learning to mimic the communication style of key players. If patience is a virtue, then these cybercriminals are positively saintly.

The payoff for their silent reconnaissance comes when the office empties out for the holidays. Like a cat waiting for the canary to stray a little too far from the perch, they pounce. In one particularly disastrous case, an attacker posed as a trusted colleague and convinced an eager junior employee to make critical configuration changes. The result? A perfect storm of social engineering and operational vulnerability, proving that sometimes, the simplest tricks are the most devastating.

Holidays: A Hacker’s Playground

Holidays are, for most people, a time of joy, rest, and overindulgence in questionable desserts. For cybercriminals, they’re a strategic goldmine. As security teams downshift into maintenance mode, attackers ramp up their efforts, exploiting reduced staffing and slower response times.

This isn’t a hypothetical concern, either. The discovery of the infamous Log4j vulnerability at the end of December 2021 coincided with many companies operating on holiday skeleton crews. The result? A mad scramble to patch systems while attackers gleefully exploited the delay. It’s a scenario that should send shivers down any cybersecurity professional’s spine—or at least prompt them to reconsider taking that week off between Christmas and New Year’s.

Planning for the (Inevitable) Worst

If the holidays are an annual invitation for disaster, then preparation is the RSVP that says, “Not today, hackers.” The key, of course, lies in planning. This isn’t the slapdash sort of planning you might use for a last-minute vacation; it’s more like planning a military operation, complete with escalation paths, automated defenses, and enough redundancies to make even the most determined attacker break a sweat.

Consider this advice from Ed Skoudis, a seasoned security expert, who likens holiday staffing plans to a game of Tetris: You need to fill every gap, anticipate every move, and never leave your most junior staff alone with the keys to the castle. Add in some extra measures of verification—callback phone numbers, video chats, and maybe even a few well-placed guilt trips—and you’ve got yourself a solid defense.

Technology to the Rescue (Mostly)

Automation and technology are the unsung heroes of holiday cybersecurity. Tools that monitor systems, detect anomalies, and send alerts to the right people at the right time can make all the difference when half the team is off sipping eggnog. For example, some companies use automated Slack messages to notify employees about unusual login attempts. A simple “Is this you?” can stop an attacker in their tracks—or at least make grandma’s house the first line of defence.

Another savvy strategy is the “follow-the-sun” model, where multinational companies distribute workloads across time zones. When one region’s team is off enjoying their holidays, another steps in to cover the gaps. It’s not foolproof, but it’s certainly better than leaving everything to chance—or to a well-meaning intern.

The Human Element: Collaboration and Paranoia

While technology plays a critical role, it’s the human element that often determines whether an attack succeeds or fails. Isolation, especially during skeleton crew periods, is a breeding ground for mistakes. The best decisions, as Mark Lance of GuidePoint Security points out, happen when people aren’t alone. Even junior staff members need to know they can escalate concerns without fear of judgment—or worse, dismissal.

But perhaps the most valuable lesson of all is this: Paranoia is your friend. If something feels off, verify it. Trust but verify, as the saying goes, because in the world of cybersecurity, a little scepticism can stop a catastrophe.

‘Tis the Season for Vigilance

As the holiday season approaches, organizations would do well to remember that attackers don’t take vacations. They watch, they wait, and they strike when defences are at their weakest. The good news? With the right combination of planning, technology, and a healthy dose of vigilance, companies can keep the wolves at bay.

So, as you sip your cocoa and settle in for the holidays, spare a thought for the security teams working tirelessly to keep the digital lights on. And if you’re one of those lucky few tasked with defending the castle this season, remember: Stay alert, stay suspicious, and whatever you do, don’t trust that “urgent” Slack message without a callback number.