Quick update. I ended up calling the customer service desk, and they ended up transferring me to reservations. At first the reservation rep didn't seem to know the rules of the gold guest upgrade, but after realizing my fare code (K) was still eligible, she ended up upgrading me. I thanked her as I knew this was no fault of Alaska's. She did disclose to me that it looked like someone had cancelled my original ticket (she could see it was booked by a travel agency), but minutes later a new ticket was purchased by me ("you") and not a travel agency. Obviously it wasn't really "me" but series of events sounds weird. She suggested I call chase travel to see what happened, but I tried calling a couple times and there were 20+ minute wait times so haven't attempted to call again yet.