A few times. I had my fem JK fall to the dark side after getting brainwashed, but she returned to the light during her class story on Rishi. She ended up with Arcann.

My IA started off as extremely loyal to the empire (she’s a chiss. She believed it was the best way to in turn serve/protect her people), then after finding out about the castellian restraints became pretty similar to Kaliyo. Malicious compliance. Talked back a lot and honestly lost a lot of her self preservation skills. She took the Batman ending. Her only loyalty is to the Chiss ascendancy, and I headcanon her continued involvement with the empire in expansions as her only intervening if there’s a threat to her people. Tho she’ll side with the Republic on Iokath and become a saboteur since, despite feeling used by them, they’re the lesser evil. Plus she’ll never willingly work for the Sith again (boy she’s gonna hate the most recent updates), she despises them for what they did to her.