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July 22, 2013 – Flight 345: A Boeing 737-700 (registration N753SW) suffered a hard landing at New York's LaGuardia Airport after a flight from Nashville International Airport. The nose gear collapsed and penetrated the electronics bay, causing the aircraft to slide off the runway. The captain was dismissed, and the aircraft was scrapped. Ten passengers sustained minor injuries.

August 4, 2016 – Flight 149: A Boeing 737-300 (registration N368SW) suffered a nose gear collapse during pushback at Baltimore/Washington International Airport after a tug operator exceeded safe towing speed. The aircraft sustained severe damage and was written off. No one was injured.

August 27, 2016 – Flight 3472: A Boeing 737-700 (registration N766SW) suffered an uncontained engine failure while en route from New Orleans to Orlando, damaging the engine nacelle and fuselage. The aircraft diverted safely to Pensacola International Airport. No one was injured.

April 17, 2018 – Flight 1380: A Boeing 737-700 (registration N772SW) suffered an uncontained engine failure while en route from New York–LaGuardia to Dallas, causing debris to shatter a window. Cabin depressurization partially ejected a passenger, who later died from her injuries. Eight other passengers sustained minor injuries.

Controversies and passenger incidents

In October 2019, a Southwest flight attendant filed a lawsuit against the airline, claiming that two pilots had livestreamed footage from a camera hidden in the plane's toilet to an iPad, and that one of the pilots said that such cameras were a "top-secret security measure" installed in all of the airline's 737-800 aircraft. Southwest and the pilot union stated that the film was a hoax and a "poor attempt at humor" by one of the pilots, who had previously recorded himself on a different aircraft, fully clothed.

In February 2020, a report conducted by the DOT inspector general found that Southwest was flying airplanes with safety concerns and that the Federal Aviation Administration was failing to properly oversee the airline.

Citing four whistleblowers, federal investigators with the US Office of Special Counsel released a report on July 27, 2022, that follows up on the 2020 DOT inspector general's report. The 2022 report claims that Southwest stonewalled Federal Aviation Administration (FAA) investigations into maintenance and piloting safety lapses, and criticized the FAA for failing to adequately oversee the airline, stating that senior FAA staff "mismanaged and interfered" with investigations "in the face of SWA's intimidation tactics". The report accuses Southwest of misusing the FAA's Aviation Safety Action Program (ASAP) to hide pilot errors, while accusing the FAA of failing to adequately oversee Southwest's mechanics, and of failing to adequately vet maintenance records provided by the airline for forty-nine 737 aircraft purchased from foreign carriers whose documentation practices did not meet FAA standards.

Christmas 2022 meltdown

The airline experienced severe delays and thousands of flight cancellations starting on December 21, 2022, and continuing through Christmas. Many cancellations were due to bad weather from the severe late December winter storm across much of the United States, but industry experts and SWAPA also blamed inadequate staffing and the airline's "outdated" employee scheduling system, citing reports of pilots awaiting work assignments for up to eight hours. On December 26, the airline initiated a massive system "reset", preemptively canceling thousands of flights and halting ticket sales over concerns that travelers might buy tickets for flights that were subsequently canceled.

In December 2023, the airline reached a settlement with the United States Department of Transportation for a record-breaking $140 million fine, exceeding the previous record by a factor of roughly 30. The financial impact from the crisis exceeded $1.1 billion in losses. The settlement included a $35 million fine payable directly to the federal government. However, USDOT waived the final $11 million payment of the fine.