Fiona's bugged that they still haven't found him, and we realize that the body they've all been passing by and ignoring this whole time wasn't even Frank: He's waking up in Toronto on a snowy park bench with no idea where he is, and because it is Canada and he is an uncouth vagrant, they chuck him in jail immediately. It's Canadian jail, so it's not even really something they feel great about, and he's taken in by a Mountie, which is like getting a kiss from a Monchichi, but we do what must be done.
Frank's got no passport, so they don't believe that he's American, and of course he's doing himself no favors -- "Whole country's a bunch of parka-wearing, draft-dodging, chickenshit cowards who didn't have the balls to stay home and fight the Vietcong to preserve our American way of life!" -- and finally this dude recognizes his "Chicago" accent among the annoying James Lipton Fellatio speeches William H. Macy likes to deliver in this role every five seconds, because he got his Economics PhD at the University of Chicago. He offers to help in exchange for a cigarette or cash -- neither of which Frank has, of course -- and then asks for a "reach-around hand job" through the bars, which... If you don't know what a term actually means, I say just avoid it.
It's not even a good joke anyway -- What, being in the drunk tank overnight changes a man so desperately? -- but then, by misusing the central phrase of the joke, rendering it incomprehensible, you've caused two problems. Three, if you count the ongoing gay joke that this show thinks it's not telling. Not that I have the time or the inclination to tell you what "reach-around" actually entails, but... Maybe they do things differently in Canada.
Tony brings over an email from the Embassy explaining Frank's in Canadian lockup -- "He admitted to drug charges, but that's before they accused him, so they're thinking he's a juicer headcase" -- but it doesn't matter anyway because it's Frank Gallagher: They just want him off Canadian soil, and the US doesn't want him back. Well, not without a passport, although if they knew Frank that wouldn't change things. So he needs to get an emergency passport at the Embassy, which involves sending illiterate Kev -- who does have a passport and is probably the only one -- to get him through the paperwork and grab some cheap pharmaceuticals for one of Veronica's many enterprises (Tony's uncomfortable/adorable). Except, they remember, the border patrol asks for proof of insurance to get back in, and Kev doesn't have that.