I was a cadet as well, and I've also adjusted the travellers on my benefits a few times. From my experience it takes a day or two for the Skywest travel page to sync with mainline travel programs. I would make sure you have your travellers set up a few days before the 18th and then give it a day or two and it should be good to go. Worst case scenario by the 20th or 21st it should be activated.