My filly Wiry Feeling is working with random jockeys, although she has them assigned…
@Hilda_with_Clicker
Out of curiousity, which jockey do you have assigned as her primary jockey? I had recurring issues with one particular jockey in the past doing this on several horses. I need to check my notes to see which one it was…and then check any ponies I have currently assigned to him/her.
She has K. Berry as her first jockey.
I want to say if multiple horses have the same primary jockey, that during workouts that jockey isn’t “available” so you get choice 2, 3, or random for some horses like in races. I could be wrong, though. I feel this has always happened with Berry.
Maybe! But her other two are Mitchell and Stroud, and she works with everyone else… seems random.
Of course I’ve deleted my notes 
…but I know I swapped all horses assigned to that jockey to others so the issue wouldn’t persist. I looked back through most of my ponies, though, and no one has K.Berry assigned. Pretty sure that’s the “bad” jockey who passes all his morning workouts to random trainers each day.