I assume the out/in were blank as autofill will not replace an existing value. Also if the entry is locked/closed it won't be touched. Have you tried the autofill now button in the entry itself to command the autofill?
Looks like the leg "closed" out before the times auto updated. When I looked at the leg, it had defaulted to the "scheduled" times instead of updating the "actual" out/in times for the DH. Is there a timeframe the program has to update the times before it closes the leg?
The second screenshot shows the screen just prior to me updating the times manually. I had to "unlock" the screen to update the times.