Caldwell later moved to New York City to continue her career. She performed regularly at NYC venues, including Drom, Milk River, and the Village Underground. Caldwell says one of the major moments of her young career came when director/comedian Tyler Perry attended one of her shows and posted about her performance on Facebook; “One of my favorite spots in NYC, the Village Underground. Ron Grant’s open mic night. Listen to this girl. SHE’S AMAZING!!! Her name is Ali Caldwell. So much fun.”

In 2014, Caldwell had the opportunity to tour in Russia, performing 40+ shows that year. Caldwell later provided supporting vocals for Christina Aguilera during her record-breaking concert at Mawazine, one of the largest music festivals in the world which takes place in Morocco. To date, Caldwell has also headlined five multi-city tours in Europe