Don't Let Security Habits Check Out for the Holidays
Your team isn't getting careless in December. They're rushed, traveling, and buried in shipping notices, and scammers plan for exactly that. Here's a 10-minute reset built for the season.
To keep cybersecurity habits strong over the holidays, give employees a short seasonal reset instead of another long training: slow down on anything urgent, verify every "quick favor" involving money or sensitive data through a separate channel, follow travel and device policies, treat shipping and order emails with suspicion, and know exactly who to contact when something feels off. Ten focused minutes before PTO starts beats an hour-long session nobody remembers.
Why do cybersecurity habits slip during the holidays?
Holiday security lapses rarely come from employees who stop caring. They come from people working under different conditions: deadlines before time off, coverage gaps, travel, personal shopping on work devices, and inboxes full of shipping notices. Owners and managers feel it too.
Attackers know this calendar too. Phishing, impersonation, and payment fraud are year-round threats; December just makes them far more likely to work.
That's why "don't forget your security training" falls flat. What helps is reframing the basics around situations your team will face between Thanksgiving and New Year's.
What are the five holiday security habits every employee needs?
Each habit is a universal security truth, reframed for the way work actually looks in November and December.
1. Slow down when something wants you to hurry
Urgency is the scammer's oldest lever, and it blends right in before PTO.
2. Verify the "quick favor"
Confirm any request for money, credentials, or sensitive data through a separate, trusted channel.
3. Don't let convenience win when you travel
On the road, company policy, not convenience, decides which networks, devices, and apps are used.
4. Think before you click the holiday bait
Shipping updates and order confirmations make perfect disguises. Go to the source, not the link.
5. Know who to ask when something feels off
The most important habit: a simple way to report anything suspicious, even when half the team is out.
How do scammers use holiday urgency against your team?
Urgency is a tried-and-true social engineering tactic, and it rarely works better than before a holiday break. When everyone is wrapping up projects, a rushed request doesn't look out of place. Watch for messages like these:
Manufactured urgency is built to override skepticism. Our rule of thumb for clients: the more pressure there is to hurry, the more reason to stop and make sure everything checks out.
Why should every "quick favor" be verified?
In high-stress months, employees want to be accommodating, especially customer-facing staff and managers juggling many teams. Good security means overriding that impulse in one case: any request for sensitive information, payment changes, or credentials must be verified.
If you know the person supposedly making the request, contact them by phone or another trusted method, never by replying to the message itself. If the requester is a stranger or customer, or you simply can't get confirmation, follow an agreed-upon process that protects sensitive information while keeping operations moving.
An extra minute of checking always beats answering a minute faster. In more than 20 years of supporting New England businesses, we've seen far more damage from a rushed "yes" than from a delayed one.
How should employees stay secure when traveling for the holidays?
Hotels, airports, coffee shops, and relatives' living rooms all introduce risk. The goal isn't to stop people from working on the road. It's to make the secure way the default way.
| Situation | The holiday risk | The habit to reinforce |
|---|---|---|
| Public Wi-Fi | Unsecured or spoofed networks can expose logins and data. | Connect only through company-approved methods, such as a VPN or a phone hotspot. |
| Personal devices | Unmanaged devices may lack updates, encryption, or protection. | Define exactly what can and can't be accessed from personal devices. |
| Shadow IT | Unapproved apps put company data outside your control. | Reconfirm which tools are approved for which tasks before people leave. |
| Shared computers | Saved passwords and open sessions linger on borrowed machines. | Never sign in to work accounts on shared computers. |
| Lost or stolen devices | Busy terminals and long drives mean more misplaced phones and laptops. | Report it immediately so IT can lock or wipe the device remotely. |
Shadow IT, meaning programs used for business without company approval, tends to multiply when people improvise away from the office. None of these precautions exist to penalize travel or PTO. They simply reflect the reality of holiday remote work.
What do holiday phishing emails look like?
Picture it: you pick up your phone in the morning and scroll through everything that arrived overnight.
In all that noise, it's easy to miss that you didn't buy anything. And because many employees shop on the same devices they use for work, a click on a personal lure can become a business problem.
Even when you expect a message, check the sender and links. Better yet, go directly to the familiar website or app instead of following the link. Phishing counts on nobody pausing to wonder.
Who should employees contact when something feels off?
Every habit above comes down to knowing where to turn. Even vigilant employees will see something they aren't sure how to handle, and the answer can't be "try your best," especially when managers are on PTO.
Before the holidays, make sure everyone can answer these questions without digging for an email from last spring:
These questions are bigger than any one employee and take coordination between staff, IT, leadership, and outside vendors. Knowing when and whom to ask sits at the heart of good cybersecurity hygiene.
Do employees need more security training before the holidays?
Usually, no. Another hour-long session is rarely what a team needs in December. A short, practical reminder lands better.
The hour-long session before break
- Badly timedYear-end deadlines keep attention low.
- Too broadIt covers everything, so nothing seasonal sticks.
- Too technicalIt buries the handful of behaviors that actually matter.
The 10-minute holiday reset
- BriefFits into a team meeting or one email.
- SeasonalBuilt around travel, PTO coverage, shipping lures, and payment pressure.
- ActionableIt ends with one clear way to report anything suspicious.
Remind employees to slow down, verify unusual requests, follow policy while traveling, and know where to turn. Leave the technical details, like monitoring, patching, and email filtering, to leadership and your IT team.
What does holiday cybersecurity mean for RI, MA & CT businesses?
For businesses across southern New England, a holiday slip-up can create obligations that last well beyond the season.
Massachusetts: written security programs
201 CMR 17.00 calls for a written security program, including employee training, for businesses holding residents' personal information. A documented holiday reset supports it.
Rhode Island: breach notification
The Identity Theft Protection Act generally requires notifying affected residents within 45 days of confirming a breach. A December phish can mean January notification letters.
Connecticut: a 60-day clock
Connecticut requires notifying affected residents within 60 days of discovering a qualifying breach, so fast internal reporting protects your response window.
Snow days and remote access
Holiday travel and New England storms mean more remote work. Remote access tested before the first snowfall prevents risky workarounds.
That's why our North Smithfield team keeps support local and never outsourced, with dedicated consultants and onsite visits included in our plans.
Holiday Cybersecurity FAQs
Phishing increases during the holidays because attackers exploit predictable conditions: heavy online shopping, a flood of legitimate shipping emails, travel, PTO coverage gaps, and year-end deadlines that make urgent requests seem normal. Rushed employees are less likely to pause and verify.
A holiday security reset is a short, seasonal reminder, often 10 minutes in a team meeting or one email, that reframes security basics around end-of-year realities: slowing down on urgent requests, verifying favors, following travel policies, spotting holiday phishing, and knowing how to report concerns.
Employees should confirm the request through a separate, trusted channel, such as calling the person at a known phone number, never by replying to the message itself. If confirmation isn't possible, they should follow the company's agreed-upon approval process before sending money, credentials, or sensitive information.
Public Wi-Fi in airports, hotels, and cafés can be unsecured or spoofed. Employees should connect only through company-approved methods, such as a VPN or a personal hotspot, avoid signing in to work accounts on shared computers, and report lost or stolen devices to IT immediately.
Report it right away to the designated IT or security contact, even during PTO. Fast reporting lets IT contain the problem, for example by resetting passwords or isolating a device. Employees should not try to fix it themselves or wait until after the holidays.
A managed IT provider can review remote access, device and shadow IT policies, email filtering, backups, and incident reporting before the holidays, then monitor and respond while staff are out. A local provider can also send technicians onsite when an issue needs hands-on attention.
Security habits don't have to take a holiday
If your cybersecurity could use a check-in before travel season begins, our local team can make sure remote access, device policies, and reporting processes are ready. Schedule a 10-minute discovery call, or reach us at 401-381-5267.
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