Have you ever had that experience up here in VT or even northern NH? I really can't imagine it happening here. But yes, as I said, I would NOT request an airborne pickup if I didn't have outs. I can always stay VFR, but I may not be able to go where I intended. Usually they do not even ask whether you can maintain separation (did you mean traffic, or terrain?), and if they do, it still won't get you an immediately effective clearance regardless of what you answer. If I need to be IFR before reaching the MIA, I have to get my clearance on the ground. That's been pretty much an absolute ever since I moved here. Not sure what you mean. If you're departing IFR from the ground, it's not an airborne pickup. When I was doing an IPC a couple of months ago, we tried to get a "pop-up on the ground", i.e. a clearance from ZBW before departing, but without filing. We were told to go to FSS. I imagine the same thing would have happened if we'd been airborne. I don't really know what it is with ZBW, I hope it's a management issue that will change someday, but for now, I've learned not to even try to pick up a clearance in the air unless i can reach 5400 feet under VFR.