Cyberattacks Don’t Take Holidays: Why Hackers Love Long Weekends and How to Prepare

When your team is logging off for the holiday, cybercriminals are logging in. With Labor Day right around the corner, are you ready for holiday weekend cyberattacks?

From the infamous Kaseya ransomware outbreak to the MOVEit data breach and even the Bangladesh Bank heist, there’s a common thread: many of the most damaging cyberattacks are strategically launched over holiday weekends. Why? Because organizations let their guard down. Skeleton crews, delayed response times, and relaxed monitoring create the perfect conditions for a well-timed attack.

In fact, a staggering 91% of ransomware payloads are deployed outside of regular business hours. That means nights, weekends, and holidays aren’t just time off, they’re prime time for threat actors. So how can you defend your organization when most of your staff are off the clock?

Let’s look at some infamous holiday-timed cyberattacks, why they’re so effective, and what your organization can do now to prepare.

Why Are Holiday Weekends So Dangerous for Cybersecurity?

“Every time a holiday comes around, I get a little PTSD,” said LMG Security’s Founder Sherri Davidoff. “Kaseya, MOVEit, Krispy Kreme—they all hit during long weekends. It’s not a coincidence.”

What makes holidays such attractive targets for cyberattacks?

• Reduced staff: Senior team members are often away or off-duty.
• Delayed response times: Alert fatigue, minimal monitoring, or out-of-office contacts slow down incident response.
• Predictable behavior: Hackers know exactly when U.S. and international holidays fall, and they plan accordingly.
• Increased financial activity: Retailers, banks, and critical infrastructure often process high volumes of transactions over holidays.

Let’s look at three case studies of major cyberattacks and analyze the patterns.

Case Study: Kaseya’s 4th of July Ransomware Crisis

The Kaseya ransomware attack hit on Friday, July 2, 2021, just as the U.S. was heading into a long Independence Day weekend. The REvil ransomware gang exploited a vulnerability in Kaseya’s remote management software and pushed malicious code through a spoofed software update.

The result? Up to 1,500 downstream organizations were affected, including grocery stores and critical infrastructure providers.

“They sent ransomware out as a software update,” said Matt Durrin, LMG Security’s director of research and training. “That’s how they were able to bypass controls and detonate on such a massive scale.”

The attackers demanded a $70 million ransom for a universal decryptor. Fortunately, many businesses were able to recover from backups. But the incident became one of the largest ransomware attacks in history—timed perfectly to catch responders off-guard.

Case Study: MOVEit Breach Before Memorial Day

In May 2023, the Clop ransomware gang exploited a zero-day vulnerability in Progress Software’s MOVEit file transfer tool. They started hitting victims on May 27–28, just before Memorial Day weekend.

But Progress didn’t release a patch until May 31, days after the attack had already begun, according to researchers at Rapid7. As Sherri noted, “The attackers planned the timing strategically. They had the exploit for a while but waited until the long weekend when nobody was watching.”

Clop’s strategy worked because MOVEit is often used to store sensitive files and transfer high-value data. By striking just as teams checked out for the holiday, they ensured maximum delay in detection and response.

Case Study: The Bangladesh Bank Heist

This wasn’t your typical ransomware event. In 2016, cybercriminals stole $81 million from the Bank of Bangladesh using fraudulent SWIFT transactions that were timed across overlapping international holidays.

They initiated the transfers on a Thursday. Friday and Saturday were holidays in Bangladesh. Monday was Chinese New Year in the Philippines, where the money was routed. By the time anyone investigated, the funds were withdrawn in cash.

The takeaway? Cyberattacks aren’t just about technical exploits. They’re about exploiting timing, culture, and geography for maximum gain.

Key Takeaways: How to Protect Your Organization from Holiday Cyberattacks

You can’t stop holidays, but you can build a cybersecurity program that stays vigilant even when your team is out. Here’s how to prepare:

1. Treat Holidays as Elevated Threat Windows

Start by acknowledging the risk. Whether it’s the 4th of July, Labor Day, Thanksgiving, or another holiday, holidays are elevated risk attack windows, and your incident response team should treat them that way.

• • Schedule extra monitoring and threat detection coverage.
  • Staff up or arrange on-call rotations with backup personnel.
  • Flag high-value assets and systems for extra attention.

2. Establish and Test Off-Hours Response Plans

Sherri recalled one banking client who required CEO approval before contacting their cyber insurer—raising the question: what if it’s 2 a.m. on a holiday?

Avoid single points of failure:

• • Assign weekend and holiday decision-makers with clear authority.
  • Document and test your after-hours escalation protocols.
  • Ensure staff can reach breach coaches, insurers, and response partners.

A tabletop exercise is one of the best ways to test your procedures and iron out any issues before an attack. If you need help running one, we offer expert-led, guided tabletop exercises.

3. Harden Your Environment Now

Get ahead of known vulnerabilities and risks.

• • Patch all critical systems. Our team of experts implements Tenable One for many clients to ensure you have continuous vulnerability management from scanning to patch verification.
  • Disable or restrict remote administration where possible.
  • Conduct a quick privilege review—does everyone need access over the weekend?

4. Include Holiday Timing in Tabletop Exercises

Real-world simulations are only useful if they reflect reality. And in the real world, cyberattacks happen when your team is out.

“Sometimes I literally have people leave the room during tabletop drills,” said Durrin. “We ask the team, ‘Who’s in charge now?’”

Consider running a drill where leadership is unavailable and responders must act independently. You’ll quickly expose hidden gaps in authority, access, or communication.

5. Communicate Across Teams—and with Third Parties

Security is a team sport. That means:

• • Briefing customer support, finance, and leadership teams on increased risk
  • Confirming your MSP or cloud provider is monitoring systems 24/7
  • Making sure everyone knows who to call (and who’s on call)

The 2021 Kaseya attack proved that even well-intentioned managed service providers may be unprepared for weekend emergencies. Don’t assume your vendors are covered. Ask the tough questions now.

Final Thoughts: The Calm Before the Breach

Hackers don’t need a holiday. But they love it when you take one.

Whether it’s a criminal ring targeting shopping traffic on Cyber Monday, or ransomware gangs waiting to detonate when your team floats off the grid, the pattern is clear: Cyberattacks spike when defenses drop.

So, before your organization checks out for the next long weekend, ask yourself: are we truly ready?

Start planning now. Schedule a tabletop. Run a patch audit. Confirm your off-hours contacts. And if you’re not sure where to begin, contact us, and we can help.