In 2007, the company apologized after it was revealed they hired private investigators to infiltrate a church group and pose as congregation members to collect information on litigants seeking redress from the company. Another lawsuit was filed by the litigants over the affair against the company for invasion of privacy and fraud.

In 2009, the company 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. The court ruled in Progressive’s favor on two of the counts and the other four were dropped, pending appeal.

Also in 2009, the company was accused of ordering their advertisements off the air during the show broadcast of Glenn Beck on the Fox News Channel over comments made about U.S. President Barack Obama. Progressive responded that they never authorized their ads to be aired during Beck’s program, and they aired in that timeslot due to Fox’s error.

In 2012, the company was widely criticized online for how it handled the claims filed by the family of Kaitlynn Fisher. She died at the age of 24 when a car she was driving was hit by a car that had run a red light in Baltimore. Progressive fought to avoid payment due to Fisher’s estate. Fisher’s insurance policy with Progressive included coverage in the event of an accident with an underinsured driver. The underinsured driver was found to be negligent in a jury trial brought by the Fisher family, with the Fisher family contending that Progressive provided legal assistance to the defense. In two follow-up statements, Progressive explained that they did not “serve as the attorney for the defendant in this case” and then clarified that ” a defendant in this case, Progressive participated in the trial procedures on our own behalf.” Progressive’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. The lawyer for the Fisher family countered by noting that two of the three witnesses were not independent, adding “I have an issue with how they examined the evidence to abandon their insured” and introduced the idea the state insurance commissioner could find Progressive had acted in bad faith. 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”.