December 13, 2025

Picture this: You’re three hours into a long holiday drive. You’re tired, the kids are restless, and your daughter asks, “Can I play Roblox on your laptop?”

Your work laptop. The one with client data, financials, and access to your entire business.

You’re tempted - peace and quiet sounds amazing - but this is exactly how holiday travel turns into a security nightmare. The problem isn’t bad intentions. It’s that during the holidays, you’re distracted, tired, and out of your normal routine. That’s when mistakes happen.

Here’s how to protect your business and survive the holiday chaos.

Before You Leave: 15 Minutes That Save You Headaches Later

Spend a few minutes prepping your devices and setting expectations with your family.

Device Basics
✔️ Install all updates
✔️ Back up important files
✔️ Set auto screen-lock (2 minutes max)
✔️ Turn on “Find My Device”
✔️ Charge your power bank
✔️ Pack your own cables (never rely on hotel chargers)

Have the Family Talk
✔️ Explain which devices kids can use
✔️ Bring a dedicated family tablet if possible
✔️ If kids must use your laptop, create a separate, restricted account

Dragonfly Tip: A $150 tablet is cheaper than a security incident. Trust us.

Hotel WiFi: Where Most People Get It Wrong

Everyone checks in and immediately connects to WiFi - phones, tablets, laptops, game devices. Meanwhile, hotel networks are shared with hundreds of strangers… some of whom would love to see what’s on your screen.
Yes, fake “hotel” networks are a real thing - and they capture everything.

Stay Safe by Doing This:
• Confirm the exact WiFi name with the front desk
• Use a VPN when accessing work info
• Use your phone hotspot for anything sensitive (banking, client data, email)
• Separate work from kids’ entertainment - they can stream cartoons on hotel WiFi; you should not do business on it

The “Can I Use Your Laptop?” Problem

Kids don’t mean harm - but they absolutely click on things they shouldn’t. Pop-ups. Random downloads. “Free game!” sites. You name it. On a work device, those innocent clicks can cause real damage.

Best Practice
• Don’t let kids use your work laptop - ever.
• Offer another device instead.

If You Must Share
• Create a restricted user account
• Supervise them
• No downloading
• Don’t save passwords
• Clear browsing history afterward

Better Option: Bring a dedicated family device with zero access to your business accounts.

Streaming on Hotel TVs: The Log-Out Trap

Logging into Netflix on the hotel TV feels harmless - until you forget to log out and the next guest binge-watches on your account.

Worse: if your Netflix password matches other accounts (we know, you’d never do that)… the risk multiplies.

The Fix
• Cast from your own device
• Or set a reminder to log out at checkout
• Or skip the TV entirely and download shows ahead of time

Never log into: banking, email, work apps, social media, or anything with saved payment info.

If a Device Goes Missing

Holiday travel is chaotic. It happens.

Within the first hour:
1. Use Find My Device
2. If it’s not recoverable, remotely lock it
3. Change important passwords
4. Contact your MSP (or us) to revoke access
5. If sensitive data was stored, inform affected parties

Before Travel, Make Sure Devices Have:
• Remote tracking
• Strong passwords
• Data encryption
• Remote wipe enabled

Same rules apply if a family member loses their device.

The Rental Car Data Trap

Most rental cars store:
• Contact lists
• Recent calls
• GPS locations
• Sometimes message previews
Delete your data before returning the car.

30-Second Fix
✔️ Remove your phone from Bluetooth
✔️ Clear recent GPS destinations
✔️ Or avoid connecting in the first place

The “Working Vacation” Boundary Problem

It’s easy to tell yourself, “I’ll just check email real quick.” Three checks later, you’ve taken calls, opened documents, and used hotel WiFi more than once. That constant switching between “vacation brain” and “work mode” makes people careless.

If You Can’t Fully Unplug:
• Check email at scheduled times
• Use your hotspot, not hotel WiFi, for work
• Work from your room, not public spaces
• When you’re with family, be truly present

The best security tool? Real rest. You’re sharper and safer when you’re not exhausted.

The Holiday Travel Security Mindset

Perfection isn’t realistic. Intention is.

Just aim to:
• Prepare your devices
• Know which activities are high-risk
• Separate work from family when you can
• Protect your business without becoming paranoid
• Have a plan if something goes wrong

Make This Holiday Memorable for the Right Reasons

The holidays should be joyful - not spent recovering from a data breach because someone hopped on a fake WiFi network.
A few simple habits can keep your business secure and your family time uninterrupted.

Want help building travel-safe policies or securing your devices before you hit the road? Dragonfly MSP can help.
👉 Book a free consultation: https://www.dragonflymsp.net

Because the only holiday story you want is “Remember how great that trip was?” - not “Remember when Dad’s laptop got hacked?”