How It Became a Shopping Phenomenon—and What It Means for You

What Exactly Is Cyber Monday?

Cyber Monday is the Monday after Thanksgiving. It’s a day when retailers roll out some of their best online deals all year. No matter what gifts are on your holiday wish list, you’re likely to find a deal for them online on Cyber Monday.

When it first started, Cyber Monday was meant to be the online alternative to dealing with the crowds during Black Friday’s in-store chaos, back when shopping on the internet wasn’t as prevalent as it is today. Since then, it has grown into a major retail event of its own. In fact, many retailers now offer online and in-store deals for Cyber Week, starting Thanksgiving Day and encompassing everything in between Black Friday and Cyber Monday to increase holiday sales.

The History of Cyber Monday

Back in 2005, the National Retail Federation noticed an interesting pattern: on the Monday after Thanksgiving, there was a jump in online shopping. This had happened year after year. This was because at that time, many people had slow internet connections at home—so they waited to do their shopping until they were back at work on Monday, where the internet was faster.

Shop.org, a division of the National Retail Federation, introduced the term Cyber Monday in a 2005 press release. The name caught on. Retailers took advantage of the publicity by offering online-only deals, limited-time discounts, and free shipping to pull people in. As people grew more comfortable shopping online, Cyber Monday quickly became known as the day to grab big online bargains without battling Black Friday crowds.

By the early 2010s, smartphones took things even further. Suddenly, you didn’t need to be at a computer—you could shop on your phone from your couch, on your lunch break, or even while waiting in line at a store. This shift helped move Cyber Monday from a clever marketing idea to one of the biggest shopping events of the year.

Cyber Monday Milestones

Cyber Monday’s rise didn’t happen all at once. It grew year by year as technology and the way we shop changed. Here are some of the biggest moments that shaped it into the shopping event we know today.

2005: The Name Makes Its Debut

Cyber Monday officially launched in 2005, when Shop.org rolled out the name in a press release. What started as a simple marketing idea turned into a nationwide talking point almost overnight. Retailers jumped in with online deals, and shoppers began to treat the day as a new digital tradition.

Late 2000s: Free Shipping Changes the Game

In the early days of online shopping, shipping costs were one of the biggest reasons people hesitated to buy online. Retailers caught on and started using Cyber Monday to promote free shipping or reduced shipping fees. Now, online shopping wasn’t just convenient, it was a better deal.

2010–2013: Smartphones Take Over

As smartphones and tablets became everyday household items, Cyber Monday shopping moved from desktop computers to mobile screens. Browsing on your phone while watching TV, ordering a gift during your lunch break at the office, or even using your phone to find the best deal while shopping in-store became the norm.

2020: The Pandemic Pushes Shopping Fully Online

During the height of the COVID-19 pandemic, many people skipped in-store holiday shopping entirely. That year, Cyber Monday hit its largest online sales ever recorded in the U.S., according to Adobe Analytics. With so many people buying from home, retailers expanded Cyber Monday into Cyber Week, stretching deals across several days.

Today: Personalized Deals and Seamless Digital Shopping

Now, Cyber Monday runs on data. Retailers use analytics, algorithms, and real-time pricing tools to deliver personalized recommendations, flash sales, and targeted promotions. Mobile shopping continues to grow, and consumers have come to expect fast delivery, simple returns, and deals tailored to their interests.

The Future: AI Impacts Online Shopping

As artificial intelligence (AI) continues to evolve, it’s set to become a defining force behind the next phase of online shopping, especially during events like Cyber Monday.

AI-powered shopping dominance could reshape how deals are delivered and how quickly they’re claimed.

Black Friday and Small Business Saturday

Cyber Monday’s blitz of online deals is part of a cluster of shopping days that shape the modern holiday gift-giving season. Cyber Monday now rounds out a long holiday shopping weekend that starts with Black Friday’s doorbusters and continues with Small Business Saturday’s focus on local retailers.

Black Friday

Black Friday, the day after Thanksgiving, started in the 1950s, when police in Philadelphia reportedly used the term to describe the congestion and chaos caused by crowds heading downtown for post-holiday shopping just before the Army-Navy football game. While the trend of shopping on Black Friday grew in Philadelphia, it had a negative connotation that retailers wanted to move away from. 

By the 1980s, retailers were telling a different story: Black Friday was portrayed as the moment stores moved from operating in the red (at a loss) to in the black (profit), reinforcing its image as a crucial sales day. Today, it remains one of the busiest shopping days of the year, with chains offering limited-time in-store and online deals.

Small Business Saturday

Small Business Saturday was created by American Express in 2010 to encourage shoppers to support local and independent businesses on the Saturday between Black Friday and Cyber Monday. The U.S. Small Business Administration later became an official co-sponsor, helping promote the event nationwide. For many small, local retailers, this day has become an important part of their annual sales.

The Bottom Line

Cyber Monday began as a simple marketing idea in 2005, designed to encourage online shopping the Monday after Thanksgiving. Thanks to broadband connections, mobile devices, major online marketplaces, and increasingly sophisticated digital marketing, it has grown into one of the biggest shopping days of the year.