The card was introduced on December 4, 2006, to enhance the technology of the transit system and eliminate the burden of carrying and collecting tokens.

The first public phase of the conversion – contactless card and smartphone payments on the subway and bus systems – was launched on August 1, 2024.

Second-generation CharlieCards, a new mobile app, and new fare machines are expected to be placed in service in 2025, with the system extended to commuter rail and ferry in 2026.

[10] On June 22, 2020, a pilot program started accepting CharlieCards on the Fairmount Line, by validation at fare vending machines and obtaining proof of payment.

[25] In November 2017, the MBTA Fiscal and Management Control Board approved a $723 million contract with Cubic Corporation to replace the original CharlieCard and CharlieTicket with a new system ("AFC 2.0", for Automated Fare Collection) by 2021, that would allow fare gates to be compatible with contactless payment systems that have since been built into many credit cards and smartphones.

[31] As of May 2024[update], the second-generation CharlieCard system, including a mobile app and new fare vending machines, is planned to be introduced in 2025.

[32] The CharlieCard can store a cash balance and daily, weekly and monthly passes that allow unlimited rides during the set period of time.

[38] Physical fare media are not used on The RIDE; passengers maintain an account by web site, phone, mail, or in-person visits.

[39] Prior to 2021, if a user needed to replace an expired CharlieCard, they had to go to the Downtown Crossing pass sales office during business hours or mail the card to MBTA.

[40] They also announced plans to have the new machines dispense “tappable” paper CharlieTickets, which can be scanned on future fare card readers that were under testing in 2021.

[48][49] The MBTA continues providing the cards free of charge at pass offices, stations throughout the system and local retailers.

[52][53] CharlieCards can be reloaded,[34] and CharlieTickets can be purchased at Fare Vending Machines (FVMs) in transit stations, and elsewhere in the system, including buses.

[60] Additionally, MBTA inspectors with handheld validators were stationed at the busiest stops to deduct money from and verify monthly passes on CharlieCards, also allowing riders to enter through any door.

[64] In July 2012, the MBTA reverted to a "front door only" boarding policy on surface stations outside of peak hours to combat fare evasion.

[66][67] The "Fare Transformation" project is currently in the process of converting all surface trolley and bus lines to all-door boarding using a proof of payment (POP) system.

Security flaws in the CharlieCard technology were studied and reported in a presentation by Henryk Plötz and Karsten Nohl at the Chaos Communication Congress in December 2007, which described a partial reverse-engineering of the algorithm used in the MIFARE Classic chip.

[68] The MIFARE Classic smartcard[69] from NXP Semiconductors, owned by Philips, was reported as compromised in March 2008 by a group of researchers led by Karsten Nohl, a Ph.D. student in the Department of Computer Science, University of Virginia.

They were scheduled to give a talk about their findings at DEFCON 16 in August 2008,[73] but were stopped after a federal lawsuit was filed against them by the MBTA, which resulted in a restraining order being issued.

[78] In 2023, four Medford Vocational Technical High School students found new vulnerabilities in MiFARE Classic that allowed them edit values on CharlieCards.