It appears that the season pass might have been messed up during the recent changes that were made to Horses because I can no longer complete complete the season pass challenge "Horses, the Adventurer's Companion" whilst doing the Mountain of Eternal Winter starting area. I already traded in both the emblem that you get around level 20 and the one that you get at 51 when you travel to Media, and the challenge won't complete itself so I can't proggress with my season pass.