Caldwell then suffered from back to back ACL tears, missing the 2012 and 2013 competitive seasons. Upon returning she claimed the silver medal at her first world cup event in China earning a spot to the 2014 Winter Olympics in Sochi, Russia. She placed 10th place after a bad landing on her first finals jump. She competed again in Beijing in December 2014 winning gold, alongside her 19-year-old teammate Kiley McKinnon, who won silver. She became the first female skier to land a quadruple twisting triple back flip at the 2017 World Championship in Sierra Nevada, Spain. Caldwell won the event alongside teammate Jonathon Lillis.
