AI Meets Holidays: Helpful Tools, Best Deals and Security Tips

Last week, I asked ChatGPT to provide “five brief tips for shopping safely online for holiday gifts and getting the best deals.” Here are the results:

1. Shop from trusted websites: Stick to well-known retailers or verify familiar ones by checking reviews and ensuring the site uses HTTPS (look for the padlock symbol).
2. Use secure payment methods: Pay with credit cards or trusted payment services (like PayPal or Apple Pay) instead of debit cards for better fraud protection.
3. Beware of “too good to be true” deals: Scammers often lure buyers with unrealistically low prices on popular items. Compare prices across multiple sites first.
4. Avoid clicking on links in emails or ads: Go directly to the retailer’s website instead of following links in promotional emails or social media posts.
5. Use price trackers and coupons: Tools like Honey, CamelCamelCamel, or Rakuten can help you find discounts, track price drops, and earn cashback safely.

Not bad.

MORE HELP WITH AI

The majority of examples that I found online for this piece were from late 2024, but they are still very helpful. I’ll also share some new ideas.

To start, we have this article: "A Very ChatGPT Christmas: Savvy Black Friday Shoppers Use AI to Find Deals." Here's an excerpt: “Getting the best deals on Black Friday used to require camping out for hours outside a Best Buy or Walmart and then stampeding into a store at the crack of dawn. Now, the savviest bargain hunters are turning to ChatGPT and other AI tools to get the job done.”

And there are plenty of YouTube videos, websites and even new AI apps to help in 2025 as we head toward Black Friday and Cyber Monday.

This YouTube video came out last November with some great AI app tips:

BEWARE OF HOLIDAY SCAMS AND DEEPFAKES

There are numerous warnings and tips on how to stay safe online this holiday season, including these:

How AI Deepfakes and Scams Are Changing the Way We Shop Online: “As 89% of Americans plan to shop online during this holiday shopping season, many say they’re more concerned about being scammed online than they were last year. One big reason why—AI deepfakes.”

FBI Issues Guidance for Avoiding Deepfake Scams: “The FBI and the American Bankers Association (ABA) have issued a joint advisory warning of the growing threat posed by AI-generated deepfake scams. …”

Holiday Shortcuts Open the Door to Scams, Norton Warns: “ Holiday shortcuts are putting shoppers in scammers' crosshairs. According to the 2025 Norton Cyber Safety Insights Report: Holiday shopping, money-saving shortcuts, urgency-driven decisions, and overconfidence online are leaving millions vulnerable. Despite concern over AI-powered scams and shady sellers, nearly two-thirds (62%) of Americans say they're likely to jump on a holiday deal the moment they see it, and often without vetting the source. In fact, more than half (54%) of Americans have made holiday purchases through social media ads, up 10 points from last year.”

Hallmark Channel Stars Issue Warning After Scammers Impersonate Them: “A group of stars from the Hallmark Channel warned viewers and fans to be wary of scams impersonating them ahead of the holiday season. …”

8 alarming travel scams targeting Americans in 2025 – “From fake bookings to romance fraudsters, these sophisticated schemes are costing victims millions. …”

Merchants Start Prepping for Post-Holiday Chargeback Wave – “U.S. consumers lost more than $12.5 billion to fraud in 2024, a 25% increase from 2023, according to the Federal Trade Commission. Nearly 80% of Americans believe cybercrime intensifies during the holidays, with phishing, account takeovers and card-not-present fraud rampant in the fourth quarter.

"The scale of the problem is not confined to third-party fraud. “Friendly fraud” — when customers dispute legitimate purchases — now accounts for 75 of digital goods fraud. Chargebacks typically surge 45 to 60 days after the holidays, adding costly administrative burdens for retailers.”

I also like these tips from a surprising source: Allstate issues new guidance to protect shoppers as identity scams surge ahead of the holidays: “What scams should holiday shoppers know about this year?
These are the most aggressive scams targeting holiday shoppers this season, according to Slane:

• Fake online retail stores created using AI that mimic legitimate retailers with deep discounts and stolen branding.
• TikTok Shop scams involving counterfeit products, phishing messages from fake sellers, and impersonated influencer accounts.
• Phishing and smishing attacks where scammers pretend to be retailers, delivery services, or customer service reps asking for login or payment info.
• Package delivery scams with fake notifications that trick users into clicking malicious links or entering personal information. …”

HOLIDAY SHOPPING SAFETY TOPIC REMAINS HOT THROUGH THE YEARS

As technology changes and new approaches to shopping have emerged over the past two decades, this topic has remained an important one for governments and consumers both in the U.S. and around the world. Many of the tips, guidance and shopping fraud warnings are still relevant from more than a decade ago, even as AI and new ways of shopping with apps (and eventually with a personalized virtual agent in the coming years) emerge.

Here are some of my blogs and articles and quotes on this topic going back well more than a decade which you may find interesting, and revealing as to how things have changed or stayed the same.

2010 in CSO Magazine: Cyber Monday & Redefining Acceptable Use – Again  
2010 on govtech.com: Web Sites Struggle on Black Friday: Cyber Monday is Next: “Technology directors around the nation were watching the weekend news very closely for events regarding online sales on Black Friday (the day after Thanksgiving). No, I'm not referring to economic activity or potential impact on our nation's economy. After the troubles experienced by Walmart and others in 2008, many stores offered more doorbuster deals online. …”
2011 on govtech.com: Cyber Monday: Are You Shopping From Work?
2013 on govtech.com: Black Friday and Cyber Monday: The good, bad and ugly - with tips to help online: “Everyone loves a deal. And geeks, nerds, government technology staff and cyber pros especially like deals on new technology. …”
2014: Tips to Avoid Holiday Shopping Scams Online – “Another Cyber Monday, and more online sales records will be set. What can you do to protect yourself at home and work?”
2015 Quotes from TheStreet (CNBC): Black Friday and Cyber Monday Shopping Deals Attract Hackers – “There are numerous Black Friday and Cyber Monday scams to watch out for, including ones involving gift cards, fake ads and coupons, fake eCards and videos, said Dan Lohrmann, chief security officer at Security Mentor, …”
2017 Quotes from TheStreet (CNBC): Why Hackers Love Black Friday and Cyber Monday Deals. The holiday shopping season is primetime for hackers who are prepared with their phishing scams and malware to lure unsuspecting shoppers eager for deals via social media and online. …”
2017 on govtech.com: Best Tips for Safe Online Holiday Shopping - "How can you stay secure online (and offline) as you shop this holiday season? Whether at home or work, whether braving the mall crowds on Black Friday or surfing the Net on Cyber Monday, what should you watch out for? Here’s a roundup of some of the best advice I’ve seen from credible sources.
2020 on govtech.com: COVID-19 Turning Black Friday into ‘Cyber November’: “Holiday shopping has always brought the year’s best deals — along with plenty of new cyberthreats. This year will bring plenty of both, starting earlier than ever, as work and home life merge. …”
2022 on govtech.com: Holiday Shopping Online: Safety on Black Friday, Cyber Monday – “What are the latest online security tips as we head into another holiday season? What’s the best cyber advice, and what shopping trends should you watch out for?”
2023 on govtech.com: How to Protect Your Black Friday and Cyber Monday Shopping – “Don’t let the most wonderful time of the year turn into a holiday crisis. Here’s help to shop securely online this holiday season. …”

FINAL THOUGHTS

As I took a trip down memory lane and read through these blogs and articles from the past two decades, I noticed a few trends.

One is that even though Black Friday holiday shopping became increasingly popular in the 1990s for in-store deals (and early morning lines), the popularity spread online, giving birth to Cyber Monday in the 2005-2006 timeframe. Online shopping for gifts and deals became increasingly popular after that. (This led to challenges with “shopping online at work” for governments nationwide, which is now more commonplace for many.)

Also, we added Giving Tuesday in 2012 and Travel Tuesday in 2017.

One more, the focus in 2014 seemed to move to Cyber Week for nonstop deals around Thanksgiving. Finally, during the COVID-19 pandemic, we saw a month of deals that I started to call Cyber November.

So happy online shopping season. And remember, AI can be your friend, shopping companion and helpful tool in November and December. But the bad actors are using AI as well to try and make the scams more appealing (and harder to detect) than ever before.