As the holiday season approaches, security teams brace for a heightened threat landscape, particularly during long weekends like Thanksgiving and Black Friday. I’m thrilled to sit down with Dominic Jainy, a seasoned IT professional with deep expertise in cybersecurity, artificial intelligence, and emerging technologies. With years of experience fortifying digital defenses, Dominic has witnessed firsthand the evolving tactics of ransomware operators and the unique challenges businesses face during these high-risk periods. In our conversation, we dive into why attackers exploit holidays and off-hours, the impact of reduced staffing on incident response, and the proactive measures companies can take to stay resilient. We also explore real-world lessons from past attacks and the critical vulnerabilities that demand attention this season.
How do cybercriminals take advantage of holiday periods and weekends for ransomware attacks, and what’s a specific example or insight that shows the pressure this puts on security teams?
Well, holidays and weekends are prime time for attackers because they know security teams are often stretched thin or distracted. Over half of ransomware attacks in the past year occurred during these periods, as attackers exploit the reduced visibility into IT networks. They’re banking on the fact that many employees are on vacation, working remotely, or simply not paying close attention, which makes initial entry and reconnaissance easier. A striking data point is that 8 out of 10 companies cut staffing by 50% or more during these times, leaving gaps in monitoring and response. I recall a case during a Thanksgiving weekend a couple of years back where a mid-sized retailer I worked with got hit by a ransomware attack late on a Friday night. The skeleton crew on duty didn’t notice the unusual network activity until Monday morning, by which time the encryption had already locked down critical systems. It was a gut-wrenching moment watching the team scramble to contain the damage while knowing full well the attackers had a 48-hour head start. That kind of delay can cost millions in downtime and recovery, not to mention the stress on an understaffed team trying to piece things together.
What are the consequences of reduced staffing during holiday periods on a company’s ability to respond to cyber threats, and can you share a detailed example of how this played out in a real scenario?
Reduced staffing during holidays can be a disaster waiting to happen. When 8 out of 10 companies slash their security personnel by half or more, you’re not just talking about slower response times—you’re looking at blind spots in monitoring, delayed detection, and sometimes a complete inability to mitigate an attack in its early stages. It’s like trying to guard a fortress with half the sentries; attackers slip through unnoticed. I remember working with a financial services firm during a long Christmas weekend a few years ago. Their security operations center was down to a handful of folks, and an attacker used a phishing email to gain access through a remote worker’s unsecured laptop. By the time the team caught wind of it, the malware had spread across several servers because no one was there to flag the initial compromise in real time. It took days of round-the-clock work to restore operations, and the firm lost significant trust with clients due to the downtime. That incident really drove home how critical it is to have at least a core team with eyes on the network, no matter the season. The emotional toll on the staff was palpable too—everyone felt helpless and overworked trying to clean up the mess with limited resources.
Holiday-timed attacks, like the one on Marks & Spencer that cost over $400 million around Easter, are eye-opening. What key takeaways should companies draw from such incidents, and what specific steps can they implement to prepare?
The Marks & Spencer attack, which resulted in over $400 million in losses, is a stark reminder that holidays are not a time to let your guard down. One big lesson is that social engineering attacks spike during these periods because employees are distracted or out of their usual routines, making them more susceptible to phishing or pretexting. Another takeaway is the sheer scale of damage possible when an attack goes undetected for even a short window—attackers can weaponize that time to maximize impact. I’ve seen similar incidents, like a holiday attack on a hospitality chain where a fake vendor email tricked an employee into wiring funds just before a major holiday. The loss wasn’t as massive, but the embarrassment and operational hiccups lingered for months. To prepare, companies need to start with robust training well before the holiday season, focusing on recognizing phishing attempts and social engineering tactics. They should also enforce strict access controls, ensuring that even remote workers use multi-factor authentication. Incident response plans need to be updated and rehearsed with tabletop exercises, so everyone knows their role in a crisis. Finally, I’d stress having a 24/7 monitoring service, even if it’s outsourced, to catch anomalies during off-hours. It’s about building layers of defense so that one distracted click doesn’t bring down the house.
Why do attackers often strike between 6 p.m. and 8 a.m., as seen in over 70% of ransomware encryption cases, and how do they orchestrate these attacks to maximize damage during those hours?
Attackers target the 6 p.m. to 8 a.m. window because they know most security teams aren’t actively monitoring during those off-hours, giving them a wider runway to operate undetected. Over 70% of ransomware encryption happens in this timeframe, and it’s no coincidence—attackers aim to complete their work before anyone clocks in and notices something’s wrong. They often start with reconnaissance weeks in advance, using phishing or stolen credentials to gain a foothold, then lie low until the perfect moment. Once they strike, they deploy encryption tools across as many systems as possible, knowing it can take hours to lock down a large network. I’ve seen this pattern in an incident with a manufacturing client where encryption kicked off at midnight on a Saturday. By the time the IT team logged in Monday morning, critical production systems were inaccessible, and the attackers had already exfiltrated sensitive data for a double extortion play. It was like walking into a house that’s been completely ransacked while you were asleep—you’re shocked, disoriented, and racing against the clock to assess the damage. The strategy is calculated to exploit human limitations, banking on delayed response to amplify chaos and pressure for ransom payment.
Retailers often begin bolstering defenses months before the holiday season with training and simulations. How impactful are these proactive measures, and can you describe a specific initiative that proved effective?
Proactive measures like training and simulations are incredibly effective when done right, as they build a culture of vigilance and preparedness that can stop attacks before they escalate. Retailers, in particular, face intense pressure during the holiday season, so starting months ahead with security awareness programs and phishing simulations can make a huge difference. These exercises help employees recognize threats in real time and reduce the odds of falling for a scam during a high-stress period. I worked with a large retailer a few years back where we implemented a comprehensive program starting in late summer. It included mandatory refresher courses on spotting phishing emails, simulated attacks to test employee responses, and updated incident response plans with regular drills. During the Black Friday weekend, one of their frontline staff flagged a suspicious email that turned out to be a ransomware attempt. Because of the training, they didn’t click the link and immediately reported it, allowing the security team to isolate the threat before it spread. Seeing that program pay off was incredibly rewarding—it’s like watching a well-rehearsed play come together under pressure. The key is consistency and realism in these preparations; half-hearted efforts won’t cut it when attackers are at their most aggressive.
With holidays bringing increased risk, what do you see as the most pressing vulnerabilities for companies right now, and can you walk us through a scenario that illustrates how these risks play out?
Right now, the biggest vulnerabilities are around remote work setups and insufficient off-hours monitoring. Many employees are accessing corporate networks from personal devices or unsecured locations during holidays, creating entry points for attackers. Add to that the reduced staffing—again, 8 out of 10 companies cut back by 50% or more—and you’ve got a recipe for delayed detection. Another weak spot is outdated incident response plans that haven’t been tested under holiday conditions. Let me paint a picture with a scenario I encountered: a mid-sized company had a significant portion of staff working remotely over a holiday weekend. An attacker used a phishing email to compromise a remote employee’s credentials, gaining access to the VPN late on a Friday night. With no one monitoring the network overnight, the attacker moved laterally, encrypting data across key servers. By Monday, the company was at a standstill, unable to process orders or access customer data, and the small on-call team was overwhelmed trying to figure out where the breach started. The frustration in the war room was thick—you could feel the tension as everyone realized how preventable this could’ve been with better monitoring or updated protocols. These risks aren’t theoretical; they’re unfolding every holiday season.
Some ransomware groups take breaks during holidays, like Black Basta pausing from Christmas Eve to mid-January. How does this impact security planning, and what’s a detailed strategy businesses can follow to stay prepared during these lulls?
It’s true that some ransomware groups, like Black Basta, scale back operations during specific holiday windows, such as Christmas Eve to mid-January. While this might seem like a breather, it’s a double-edged sword for security planning. On one hand, it can tempt businesses to relax their guard, assuming the threat is lower; on the other, it’s a chance for other opportunistic attackers to fill the void, or for the same groups to return with renewed vigor after their break. You can’t afford complacency. I’ve seen companies get lulled into a false sense of security during these periods, only to be blindsided by smaller, less predictable actors. A solid strategy starts with maintaining consistent monitoring, even during perceived lulls—don’t scale back your security operations center just because one group is on hiatus. Next, use this time to run thorough system audits and patch vulnerabilities, ensuring your defenses are tight for when activity spikes again. Conduct tabletop exercises to simulate attacks and refine response plans, involving staff at all levels so everyone stays sharp. Finally, communicate with your team to keep awareness high—remind them that other threats don’t take holidays. I recall advising a client to double down on these steps during a quiet holiday period, and it paid off when they caught an attempted breach in early January, just as major groups were ramping back up. It’s about staying one step ahead, even when the battlefield seems calm.
What’s your forecast for the cybersecurity landscape during upcoming holiday seasons, and how should companies adapt to emerging threats?
Looking ahead, I expect holiday seasons to remain a hotbed for cyber threats, especially as attackers refine their tactics with AI-driven phishing and more sophisticated social engineering. The trend of targeting off-hours and weekends will likely intensify, with encryption and data exfiltration becoming even stealthier to evade detection. We might also see smaller, agile threat groups stepping up during lulls left by bigger players, creating unpredictable risk patterns. Companies need to adapt by investing in automated monitoring tools that can flag anomalies 24/7, reducing reliance on human oversight during low-staff periods. They should also prioritize employee training year-round, not just before holidays, to build a resilient first line of defense. I’m particularly concerned about the rise of double extortion tactics, where data is stolen and systems are locked, doubling the pressure to pay ransoms. It’s going to be a tough road, but with proactive planning and technology, businesses can stay ahead. The key is to treat every day like a potential attack day, holiday or not, because cybercriminals certainly do.