To anyone who travelled by plane this last holiday season or tuned into the news, you’re well versed in the Southwest Airlines (Southwest) issues that plagued December 2022. Southwest ended up cancelling over 15,000 flights over the Christmas season, forcing thousands of stranded passengers to sleep at the airport and miss time with loved ones. With the disruptions leading to an estimated $825 million loss for the company, federal regulators have scrutinized Southwest to ensure compliance with its customer service plan and to take mitigating steps to prevent another catastrophe. This failure presents an opportunity beyond mere investigation for the Department of Transportation (DOT) to take important regulatory steps to ensure infrastructure and technology is aligned with the modern expectations of travel.