Southwest Airlines has experienced several high-profile system failures, most notably the "Holiday Meltdown" of December 2022, when an outdated crew-scheduling software system crashed during a major winter storm. This failure resulted in the cancellation of over 16,700 flights, leaving millions of passengers stranded and costing the company over $800 million. The root cause was identified as "SkySolver," a legacy system that was unable to handle the volume of reassignments needed during a crisis. In response, Southwest launched a massive $1.3 billion technology overhaul. While there have been minor "technical glitches" and brief ground stops in 2024 and 2025 as new systems were integrated, as of early 2026, the airline has significantly modernized its infrastructure. The 2022 crash remains a textbook case in the aviation industry of the dangers of "technical debt," and it prompted the U.S. Department of Transportation to implement stricter rules regarding passenger compensation and airline accountability during controllable system failures.