[8][9] Progressive boasts being the first auto insurance company to have a website and to allow customers to purchase policies via that site.

[22] In 2012, Progressive introduced another character, a personified box (voiced by Chris Parnell) representing the company's products.

[23] Progressive later added more characters like Flobot, Mara (Natalie Palamides), Dr. Rick, and Motaur to its advertising series.

In 2019, Progressive began the At Home with Baker Mayfield ad campaign during the National Football League season.

[24] After he was traded to the Carolina Panthers in the 2022 offseason, Mayfield stated that the advertisements will end, calling it a "missed opportunity".

[25][26] In 2022, Jon Hamm appeared in several TV commercials, as himself, unsuccessfully pursuing a romantic relationship with spokesperson Flo.

Snapshot is a voluntary discount program where drivers can save money on their car insurance by sharing their driving habits with Progressive.

[30] Drivers plug a device the size of a garage door opener into the on-board diagnostic (OBD) port of their car.

The Progressive Automotive X PRIZE is an international competition designed to inspire a new generation of viable, super fuel-efficient vehicles.

The competition is open to teams from around the world that can design, build, and bring to market 100 MPGe (miles per gallon energy equivalent) vehicles.

Starting in 2021, Progressive sponsored Sesame Street on PBS Kids replacing Blue Lizard Australian Sunscreen.

[38] In 2002, the company settled with the State of Georgia in a class action lawsuit over diminished value claims brought by policyholders.

[40] In 2009, Progressive was sued for allegedly deceiving policyholders by employing illegally operated, unlicensed body shops to make repairs on vehicles for their clients in order to save money.

Fisher's insurance policy with Progressive included coverage in the event of an accident with an underinsured driver.

"[47] The company's position was that fault for the accident had not been clearly established, since three witnesses (the driver of the other car, that car's passenger, and Ms. Fisher's passenger) believed that Fisher had run a red light, and filed a motion to intervene to assert that she had been at fault, and therefore was not liable to pay the underinsured motorist claim.

As noted, Progressive lost the case and was ordered to pay the underinsured motorist claim in addition to a separate settlement with the Fisher family "to avoid a hearing before the state insurance commissioner".