You'd have to explain your logic more fully. Oswald had a long history of lying when it wasn't necessary, doing seemingly inexplicable things and doing other things just for their shock value. This is what I mean by Oswald being Oswald on his passport application. It would be exceedingly unlikely, it seems to me, for a Cold War defector being guided by an intelligence agency to list on his passport application, for absolutely no reason, the Russia to which he would be defecting and Cuba as well. Why would he do this, or be allowed by the intelligence agency to do this, and how could he be sure it wouldn't raise red flags (no pun intended) in the processing of his application? Perhaps you're suggesting he would do something so unlikely and risky just to show he wasn't a false defector because no real false defector would do that? Well ...
Well, it didn't "raise any red flags" anyway (or so they tell us), so what difference does it make? If he was guided by "intelligence agencies", wouldn't it be those same intelligence agencies who would be looking for red flags? I'm not sure how anybody could know what a "real false defector" would or would not do.
By the way, feel free to give specific, confirmable examples of Oswald's "long history of lying when it wasn't necessary".