[9] In October 2023, the company filed for Chapter 11 bankruptcy, due to a large debt load and thousands of lawsuits alleging involvement in the opioid crisis.

One year later, Rite Aid acquired Perry, entering Metro Detroit for the first time, and expanding its presence in Michigan even further.

[26] On August 23, 2006, The Wall Street Journal announced that Rite Aid would acquire the U.S. subsidiary of Quebec-based Jean Coutu Group, including 1,858 Eckerd Pharmacy and Brooks Pharmacy stores, for US$3.4 billion in cash and issuing stock, which would also give Jean Coutu a 32% equity stake in Rite Aid.

On January 4, 2008, Rite Aid announced the closure of all 28 of its stores in the Las Vegas Valley, and the sale of patient prescription files from the market to Walgreens.

In 2015, Rite Aid purchased EnvisionRx, a pharmacy benefit manager, which owns subsidiary PBMs MedTrak, Connect Health Solutions, and Smith Premier Services.

[38]On October 27, 2015, Walgreens Boots Alliance announced that it expected to acquire Rite Aid for $9.4 billion, pending shareholder and regulatory approval.

[44] In January 2017, Rite Aid and Walgreens further delayed the merger's closing to July, and reduced the sale price to approximately $6.8 billion.

[44] 1199SEIU United Healthcare Workers East, a labor union representing 6,000 Rite Aid employees, announced its opposition to the merger on January 31.

[46][47][48] Further negotiations led to a fourth revised deal, in which Walgreens would purchase 1,932 Rite Aid locations for $4.38 billion, which was approved by the FTC on September 19.

[52][53] On February 20, 2018, Albertsons announced plans to acquire the remainder of Rite Aid, in a merger of equals, subject to shareholder and regulatory approval.

[56] In October 2020, Rite Aid announced the acquisition of the privately held Bartell Drugs, a 67-location Seattle-area chain, for $95 million.

[60][61] As of fiscal year 2022, Pennsylvania, with 494 stores, is home to the largest number of Rite Aid locations, followed by California and New York, with 487 and 281 respectively.

[62] On August 25, 2023, Rite Aid announced that it was preparing to file for Chapter 11 bankruptcy protection within the coming weeks, in an effort to settle federal and state lawsuits over the company's role in the opioid crisis.

[69] On October 18, Rite Aid warned investors that it may not be able to survive its bankruptcy filing and might have to permanently shutter or sell all of its remaining stores over the next twelve months.

[81] On December 21, Rite Aid cancelled an auction for its Elixir division after no other higher bids came in, and would sell the insurance-related company to MedImpact Healthcare Systems for approximately $575 million.

[82] In June 2024, the Detroit Free Press reported that Rite Aid was preparing to close all remaining stores in Michigan.

[83] Soon thereafter, the chain filed a WARN notice disclosing plans to close its Waterford, Michigan distribution center in August 2024, laying off nearly 200 employees.

[94][95][96] On July 25, 2004, Rite Aid agreed to pay $7 million to settle allegations that the company had submitted false prescription claims to United States government health insurance programs.

[97] On July 14, 2022, Rite Aid inked a $10.5 million settlement with counties in Georgia, North Carolina, and Ohio, which allowed the company to sit out the next wave of trials stemming from the opioid epidemic in the U.S., which were slated to begin against national pharmacy chains by 2023.

[98] On March 14, 2023, the United States government sued Rite Aid for missing "red flags" as it illegally filled hundreds of thousands of prescriptions for controlled substances, including opioids from May 2014 to June 2019.

[100] In July 2020, the Reuters news agency reported that during the 2010s Rite Aid had deployed facial recognition video surveillance systems and components from FaceFirst, DeepCam LLC, and other vendors at some retail locations in the United States.

[101] Cathy Langley, Rite Aid's vice president of asset protection, used the phrase "feature matching" to refer to the systems, a technical term related to the process of image feature extraction in the field of artificial intelligence for video surveillance, and said that usage of the systems resulted in less violence and organized crime in the company's stores, while former vice president of asset protection Bob Oberosler emphasized improved safety for staff and a reduced need for the involvement of law enforcement organizations.

[101] In a 2020 statement to Reuters in response to the reporting, Rite Aid said that it had ceased using the facial recognition software and switched off the cameras.

[101] The Home Depot, Menards, Walmart, and 7-Eleven were among other US retailers also engaged in pilot programs or deployments of facial recognition technology at that time.

Rite Aid said that the selection of locations was "data-driven", based on the theft histories of individual stores, local and national crime data, and site infrastructure.

[102][103] A partnership with Drugstore.com in June 1999 allowed customers of Rite Aid to place medical prescription orders online for same-day, in-store pickup.

The new service is called Counter[104] and launched in the US after being used in the UK with the Next clothing chain and in Italy with Giunti Al Punto Librerie, Fermopoint and SisalPay stores.