You're right, mine didn't update until it was already on the flight from what I remember (and it had that weird double departure scan). I'm sure you'll get word that yours is safe and sound in Alaska soon
I'm trying to stay positive and hope that mine is on the next flight from Louisville to Newark, which departs in about 30 minutes - no departure scan yet, but hoping there's still plenty of time. I tried to chat UPS today to see if they could provide me with an estimated delivery date and their response was "we're not sure, just keep tracking your package" -__-