Headcanon that Ransom and Holster periodically roadtrip up to NY (where there are Tim Horton’s) during Roll up the Rim season. Or you know which ever closest state has a Timmies.
Did Jack go, you ask?
99% of the time he says no, because obviously he had to concentrate on school work and captain-y stuff. Also the coffee at Annie’s is probably superior anyway. But Rans and Holster usually bring him back some sort of drink anyway cause they’re good bros. Jack rolls his eyes but goes along with it anyway, sometimes warming up the now cold coffee or just dumping it. Jack’s cup is almost always a winner, which pisses Holster and Ransom off to no end, but they keep doing it anyway.
The first year after Jack has graduated, the boys show up on his doorstep the day Roll up the Rim starts with a cup for him.
Jack does not cry because he loves his friends and their stupid traditions. He doesn’t. Really.